The Viall Files - E294 Olivia O’Brien - I’ll Write a Song About You
Episode Date: July 21, 2021On today's episode of The Viall Files we are joined by recording artist, Olivia Obrien. Olivia uses so much of her personal life in her writing and music and she is not shy about sharing those stories... with us today. Relationships, mental health, insecurities, and the challenge to overcome it all, not only leads to a reflective and honest conversation between Nick and Olivia, but also to some really amazing music. “I popped out of the womb and started flirting.” Please make sure to subscribe so you don’t miss an episode and as always send in your relationship questions to asknick@kastmedia.com to be a part of our Monday episodes. For merch visit www.viallfiles.com today! Don't forget to nominate The Viall Files for a People's Choice Podcast Award: https://www.podcastawards.com/ THANK YOU TO OUR SPONSORS: Beam: http://www.beamtlc.com/VIALL or go to http://www.beamtlc.com and use code VIALL at checkout. Subscribe to dream for awesome perks like free delivery and 35% off your first month. Vizzy: http://vizzyhardseltzer.com/VIALL To find out where you can purchase Vizzy. Upgrade your hard seltzer to Vizzy Masterclass: http://www.masterclass.com/VIALL for 15% off an annual membership. Wondery - Even The Rich: Listen to the latest season of Even The Rich: The Making of Madonna on Apple Podcasts, Amazon Music, or you can listen ad-free by joining Wondery Plus in the Wondery app. Wondery…Feel the Story. Episode Socials: @viallfiles @nickviall @oliviaobrien See omnystudio.com/listener for privacy information.
Transcript
Discussion (0)
What's going on everybody welcome back to another episode of the vile files I am your host Nick
joined by the dynamic team of Chrissy Alley and Amanda. How is everyone doing today?
And Travis is here, recently engaged.
Congratulations, Mr. Romance.
Himself, our sound engineer
fixing the mic.
Everyone good? Great? Everyone's fine?
Yeah. I wanted to ask you,
are you a member of SAG?
Yes. Should I join? Should we be
members together? Yeah.
Can you... Yeah. Can you?
Yeah.
I feel like a professional actor now.
Congratulations.
Nice flex.
I also got an apartment, so we're on the up and up.
Great.
I started a new job as a matchmaker, and I love it.
What do you mean?
I'm a matchmaker now.
How does that work?
How does one become a matchmaker?
So I work with clients, and I do an intake call with them, get a sense of what they're looking for. And then I go through both,
like we have our own database, but then we also have external recruiting efforts.
And so it's so cool because I just get to spend like hours talking about to people about like
what they look for in a partner and a lover. And it's just like a fascinating insight into
human condition and dating. Did you start already?
Yeah, I did. I have four clients. Did you start, start already? Yeah, I had did.
I have four clients. Have you set anyone up yet? I'm in the process. So we have to screen anybody who we want to set our clients up with. Like we have to screen them on a separate call. So I have
some screenings booked for the end of this week. It's what happens? Like, how do you get rate?
Like how, like a performance review performance review like how how are you reviewed
like what if does someone need to get married within the first year on the job or how like how
does one define success well there's so at the end of a date clients will fill out a feedback
form for the date so if you set people up on a lot of five-star dates or just there's sort of
like a bunch of like data things that they keep track of like how quickly you're able to find uh clients for people and it's also
just about kind of someone's own personal experience so if a client thinks you're not
doing a good enough job they can say peace i want a new matchmaker and do you have women
men clients both i have both okay i'm gonna ask more questions about this job as it
as it continues we have a great episode for you. The wonderful
and very talented Olivia O'Brien is with us today. And we talk a lot, as we always do,
about relationships. She is a young, talented, and very honest person. And by her own admission,
so much of her music is inspired by her own personal life and relationships that she's had. And we have a fun conversation about her career and her music and her relationships
and all the things that we've learned along the way. So thanks for listening. I know you will
love this episode. We are back as always with you on Mondays for our Ask Nick episode. So if you are
tuning in to listen to Olivia, welcome.
We do a lot of fun things like we recap The Bachelor when it's on on Tuesday.
We also have a Q&A episode called Questions with Nick where people call in and tell us
of their relationship stories or problems.
I give them insight and hopefully help fix their problems.
So be sure to check that out.
If there's nothing else, let's get to Olivia.
Olivia, thanks for coming. Thanks for having me. Yeah. We were talking about pimple popping.
I think again, thanks for coming on. I was telling you when you came in here that
I've been on TikTok and I was just kind of on your page through the for you
page and you had one of these kind of relatable relationship things and it was and then i was
talking to my girlfriend about you and she's a big fan of your music and then i was listening
to your lyrics i know i'm not your target demo lyrics i've always liked like women like i was
a big britney spears i am a britney spears fan. Free Britney. But like, Call Her Maybe.
I'm sorry, I like it.
I don't.
So it's honest music about relationships
and we obviously talk a lot about it.
So thanks for coming on.
Thanks for having me.
So you, is that true?
I mean, music wise,
you obviously have been writing songs and making music for some time now. When you started doing it, was it always about relationships? What was always your motivation, even when you started? Or did that start when you started dating and getting into kind of romantic relationships?
romantic relationships?
Well, I've kind of been, like, I was, I popped out of the womb and was immediately, like,
flirting with everyone and, like, obsessed with boys.
And, yeah, my mom always tells me stories about when I was, like, literally two years old and she'd bring me to, like, weddings and I would, like, go up to all the hot guys
and, like, sit on their laps and, like, she said she knew that I was going to be, like,
a lot to handle as I grew up and I was like, you're right.
But I just wrote, like I I used to write songs
when I was like seven I went to Montessori school so it was very like we did like musical things
yeah until like second grade and so it was very creative and I had all these no I found all these
notebooks in my like mom's garage of all these songs I wrote when I was little they're not good
I was like seven so but they're all about boys pretty much so I was little, they're not good, I was like seven, so.
But they're all about boys pretty much.
So I think I've just kind of always
wanted to write about that.
It's been the, like other than my mental illness,
it's been the one thing that inspires my music the most,
I feel like, so.
What is your, what mental illness,
would you talk about?
All of them, every single one.
What's?
All the illness.
Anxiety? No. Yeah.
I recently got diagnosed with OCD.
I didn't know I had it until like sometime last year when I started going to therapy again.
But I've always had, I had depression since I was like 11.
How did you come to be diagnosed?
What was like maybe something that you discovered like if someone's listening and
wonder if they have it because i feel like those sometimes there's a lot of these kind of
uh diagnosis that people wonder and they don't know and what was the thing that kind of made
you realize that you finally with ocd yeah um well i knew that i always had anxiety and i didn't
realize ocd is like it's an anxiety disorder but people always think of it as like, Oh, someone who has to keep their space super clean and organized. And like, that's,
that's the stereotypical OCD thing. And I've never been necessarily the most organized or
clean person. I mean, I'm not like disgusting, but I never keep my room perfect. Yeah.
I've wondered if I sometimes am, and I'm definitely not that I have a friend who would,
he would like, everything has to be perfect. and i actually used to like fuck with them and and but i was i'm wondering
yeah and please continue like what was it what does it mean what's not true about the stereotypes
and what i mean how do you suffer from it can be true like there are people that are like that
that's where the stereotype came from.
There's some truth to it, but it also it's obsessive compulsive.
So just having like weird things that you obsess over that you can't control in your brain.
Like I had a really, I used to have really bad death anxiety.
I still do sometimes, but like I would lay awake at night just like thinking about all these things that I can't control about everyone I know and love dying and me dying and what happens, blah, blah, blah.
And I would like have panic attacks every night before I would go to sleep and I wouldn't be able to sleep and uh I
also really the one thing that is kind of stereotypical OCD I guess is I'm really weird
about my bed like I if someone comes into my room and like sits on my bed I like I have like a I
can't do it it like gives me so much anxiety or like and I'm not I'm not super super organized
but if someone comes in and touches things in my room I get upset like I like like and I'm not super, super organized, but if someone comes in and touches things in my room,
I get upset.
Like, and it's not like I get angry.
It's this weird feeling of like,
please don't do that.
Wow, okay.
Yeah, so. But your bed though, how do you introduce,
I mean, literally a guy into your bed?
I don't invite men to my house.
I always go to them.
Interesting.
Yeah, I don't like people in my space
boyfriends well i've had like two boyfriends in my life okay well how did that work well they would
come over and it would be it was fine one of them was like the first like actual boyfriend that i
had i was like 17 and he was 24 okay and i it's really like it was kind of looking back. I'm like, that was not good.
And I was like, we only dated for like a month and I, and I went on tour and I was like,
I can't see this.
Every time we would hang out, he was like a club promoter.
And I was like, oh God, my life.
Fuck.
Okay.
Yeah.
He was like a club promoter.
We've all done some shit where we look back and be like, ah.
I was 17, like whatever.
But I, he would, we would go to the club and we would get drunk and we decided we were dating when i
was drunk in the club and then i would break up with him and i would go out to that club and we
would like get back together when i was drunk and this is a 24 year old man like it's so and like
that's so not okay whatever but he would like come over every once in a while after like club hours
and we would just like fall asleep in my bed or whatever.
What's the club?
What club was it?
Oh,
I was,
I was going to guess the other one.
One Oak.
One Oak.
Oh God.
I mean, they're all the fucking same shit basically.
The club promoter story is a common story,
but that's okay.
You let You learned.
And then your second boyfriend.
He would sleep.
Actually, I never even went to his house.
I feel like whoever has the power in the relationship is the person that, like, you go to their house.
That's what I realized.
Like, I had all the power in that relationship,
and I never went to his house.
He always came to me.
But it was like he knew his place. Whoever has the power in the relationship and i never went to his house he always came to me but it was like he
knew his place like he would sit in his power in the relationship like whoever's house you are
consistently going to they have all the power it's interesting i've never thought about that
it's been at least always true for me it's also like really insightful i don't a lot of people
i talk about power a lot in relationships but it's one thing people don't talk about or honest with.
Because even healthy relationships, power always exists,
and it's kind of something we struggle with early on.
And even when you're in a healthy relationship, the power can change a little bit.
You almost sometimes feel it,
especially the worst part is when you feel like you have the power.
And then one day you wake up and you feel a little less powerful and even maybe
that's okay.
But it's interesting.
You say that.
I think you're probably right.
Yeah.
The,
whoever,
whoever has the power,
it's that their house,
is it because they're lazy?
No,
I don't.
I,
it also like,
there are definitely instances where it's like,
okay,
if one person has like five roommates and one person lives alone,
you're obviously going to go to that person's house.
But like,
I just think about consistently how it's been with me like the
guys that i've really really liked that didn't want to date me like i would always go to their
house they never came over so when you thought about that is that something you thought about
after the relationship was over you kind of reflected on it or were you aware of that power
dynamic when you were dating them um i think it's just something over the years i've just come to
realize i mean my friends have talked about it because like we all kind of have the same types of relationships
and like the same kind of asshole guys. And so it's just kind of been the same patterns over
and over again. And we kind of noticed like, oh, well, that happens with you and this happens with
me. That's crazy. This happened with him and him and him. So do you like again, because like when
you write your music, it's really insightful. It's really kind of reflective and i i guess as a songwriter you're kind of prone
to do that i give like a lot of relationship advice in the show people always ask me do i
take my own advice do i apply it in the moment i do try do you try as well as how does that work in theory you're honestly you don't i try i mean i'm 21 so i
part of me is like i do i like a relationship sounds like it could be nice and fun and cool
and whatever with the right person but then part of me is like so terrified that's why like every
time i do get into a real relationship i'm always the one that ends it because i'm like i don't like
i don't want this right now i want to be i want to be free until i meet the one that ends it, because I'm, like, I don't, like, I don't want this right now, I want to be, I want to be free until I meet the person that, like, I, is really
worth, like, putting that time, I don't want to say wasting my time with, but, like, putting that
time and energy into that, because I work a lot, and I like to have fun, and I like to go out,
and I like to flirt with random people, and be crazy, and I don't want to not enjoy my life right now while i i'm still
young and able to do all this stuff so i'm like kind of afraid to take my own advice so i go for
guys i know are gonna be assholes to me so that i can one write songs about it and two uh we're not
gonna bug and date so that's fine so you're you're, you're almost actively dating not to find a boyfriend.
Yeah.
But then I still,
I still get hurt by it though.
It's,
it's really shocking.
It's like,
I know,
but it's like,
I'm so self-aware.
Like I know exactly what I'm doing.
I know he's going to be hooking up with other girls.
I know he's going to like,
say whatever he wants to my face and do whatever he wants behind my back.
But I still,
there's still like a part of me that is a little bit like,
Oh,
but maybe like,
maybe he really,
maybe he really likes me.
And then I like still get hurt when they do the exact thing that I signed up
for.
Essentially.
Do you think it's your ego or do you think it's your genuine interest in
them?
I think I'm just,
I don't know.
I really,
I'm just fucked.
I think you're going to be just fine.
Like you're actively dating and don't want a boyfriend but it's but like i you know this is something that's very relatable to like
a lot of people yeah and i'm sure like if i met someone that i was like holy shit like this person
is like i will never find someone better and like this is the person for me then i would fully i'm
sure i would date them but i just haven't met that person, I guess.
There's guys that I've really, really, really, really liked
and in the back of my mind wanted to date,
but I go into it with kind of the mindset that I just explained
of it's not going to work out.
But I probably would want it to if it did, but it's not going to,
and I know that.
When it comes to recovery, performance, immunity,
and feeling less stressed, sleep is everything. And I actually found the answer to better sleep in a delicious,
healthy cup of cocoa. It's the Dream CBD Powder with Beam, and it's changed the way I sleep.
With Dream Powder, you're getting more than just quality shut-eye. You're providing your body with
sleepy vitamins and minerals. Dream is essentially a guilt-free, sleepy-induced
warm cup of organic cocoa or organic cinnamon without any calories or added sugar. And there's
proof in the powder. After taking Dream, 99% of people feel an improvement in the quality of their
sleep and 97% felt more energized the next day. Those are results I love to hear. If you want
better sleep and better days delivered every month,
subscribe to Dream for the awesome perks like free delivery and 35% off your first month.
Plus, you can pause or cancel anytime. Subscribe today and you'll save 35% by going to beam.com
slash V-I-A-L-L. That is B-E-A-M.com slash V-I-A-L-L. Or go to beam.com and use code V-I-A-L-L
at checkout. Sweet dreams.
Hey, do you like alcoholic drinks but also want to take care of your body? It doesn't even seem
like it's impossible, but it is with Vizzy. V-I-Z-Z-Y. Vizzy, Vizzy, Vizzy. Hard seltzer
crafted with antioxidant vitamin C. It's truly amazing. I love vitamin C. Can't get enough of
it. It's got 30 times more vitamin C per cup than an orange.
30 times more vitamin C per cup than an orange.
Amazing.
Comes in amazing flavors like pineapple mango, black cherry lime, strawberry kiwi, my favorite,
blueberry pomegranate, papaya passion fruit, watermelon, strawberry.
The list goes on.
There's a blackberry and lemon, also really tasty.
Vizzy is also launching its own lemonade hard seltzer in four delicious flavors, watermelon,
peach, raspberry, and strawberry,
with the same antioxidant vitamin C.
So get your vitamin C on.
Upgrade your hard seltzer today with Vizzy.
Find out where you can purchase Vizzy at go to vizzyhardseltzer.com
slash V-I-A-L-L.
That is vizzyhardseltzer.com slash V-I-A-L-L.
Must be 21 or older.
Do you like the chase I saw on a TikTokiktok you did about you know your god what
was it like this is my man and and he was very and what i liked about because like a lot of i'll
go i'll go i question all the time and and somewhere in their question uh and you know
the girl will say well he told me i didn't want to date, but, and then they'll give me all these other things he said and did
and all these kind of breadcrumbs that made him confused,
but I'm like, he literally told you he didn't want to date,
and you mentioned that in the TikTok, and yet that was like,
what do you think it is about you or other women
who will hear a guy say whenever
this isn't going to happen and yet you stick around is it because you are honest about like
what's going on or do you think it's a challenge or what do you think is causing that to happen
well i think it's just like the human condition to want what you can't have it's everything with
with dating with jobs people tell you you can't have it's everything with with dating with jobs people
tell you you can't have something and you immediately want it even if you didn't want it
before and if you already did want it before and you are attracted to this person you really like
them and they tell you oh no we can't date but like we can still hang out then in the back of
your mind you're like it's almost a competitiveness it's like oh well he doesn't he doesn't want to
date me but he still wants to hang out like i going to convince him to fall in love with me.
Like I'm going to do this.
Never fucking works, obviously.
But yeah, I think that's just what it is.
You just, you can't help it.
Okay.
Yeah.
You also mentioned on a TikTok that you realized,
you called yourself old, which I'm kind of funny,
but that you realized that everyone else has had their first love.
And then that you,
you won't be anyone's first love was kind of the,
yeah,
well,
I've,
I've had relationships and like,
I've been like fully like obsessed with guys before,
like just would drop anything and everything for them.
But those are always the guys I never dated.
And then the guys that I do date,
they may be like really, really into me and i'll be like semi into them but not
enough to be like oh my god i'm in love with this person i've never had one of those relationships
that like in high school when people date it's like their first love and it's so special because
they think that they're never gonna find it ever again and it's so exciting it's the first time
it's ever happened so they're just like so obsessed with each other and it's so dramatic
i never had that with anyone ever because i didn't finish high school i moved
to la i started hanging out with all these fucking asshole guys and then whatever's happened has
happened but i i never had that experience where it's like kind of like a mutual thing like i've
been really into guys and guys have been really into me and we've dated and whatever but i've
never had that okay like a
mutual obsession do you want like if you could fast forward whenever whenever it is you meet a
guy thinking about that do you want do you wish you were someone's first love like do you care
about that it's weird i feel like i have these ideas in my head based off of just like shit i've
seen in movies and like people I know
talking about all their life experiences and then I feel like oh I'm missing out on something but
then it's like am I missing out on something because I got to go have fun while they were
in their little weird relationship that didn't work out so what's the point of that but then I
guess you learn lessons but then it's like are those lessons even worth it because you're like
16 I don't know I really truly my thoughts are all over the place so I think that's part maybe part
of the problem but it's really it's an interesting um I like I said it's an interesting relatable
thing because we like I like you said that we kind of have these fantastical dreams and fantasies
about uh like how we want love to work out for us or and being someone's first
whether it's losing your virginity or your first love and we almost kind of waste a lot of energy
trying to make that happen as opposed to like just genuinely focusing on finding a real connection
yeah I asked my audience once and I was kind of surprised by the answer. If they actually, let me ask you, do you,
do you judge people for having a lot of exes?
You meet a guy and he's like,
yeah,
I've had like six or seven girlfriends.
I've been in love three times.
Like you're subconscious.
Does your subconscious kind of be like,
I don't know.
Yes.
But only because I am so picky with people that I actually like, I mean, I guess I've dated people that I wasn't super, super into, but like actually fully dating and having like a serious relationship with someone would take them being like so fucking amazing and me being so compatible with them.
And I don't think that that many people exist in the world that are that compatible with me that I would be that into.
I just don't genuinely like a lot of people.
That's why when I do like someone,
I fucking obsess over them because it feels so rare to me.
So people that can just date a bunch of people
and commit themselves to a bunch of different people
kind of scares me.
I feel like maybe they're just very basic
and don't have a lot of individuality or unique thoughts.
So they just can get along well with everyone.
And their personality is mild
and doesn't rub people the wrong way.
And everyone likes them, which also concerns me.
Because if everyone likes you, then you probably suck.
Yeah.
Or you're not yourself.
Yeah.
If everyone likes you,
you definitely don't know how to be yourself.
True.
But on the flip side,
if you have a handful of exes,
it's like test driving, you know?
Yeah.
But I guess it depends on how serious
these relationships were.
And guys that I like,
I don't know if they've necessarily had a lot of exes,
but they've had sex with every single person
I've ever met in my life.
So that's LA. So I've just come to, it's like i just have to accept it at this point but more
more the relationships of like you know i had a couple valentine's days with a girl or a couple
okay that's already too crazy so you don't so a long-term relationship is a negative
i mean imagine all the practice he's getting to not fuck up with you
i guess it depends on like also how old they are like if they're constantly in a new relationship
then it's concerning but like if they're waiting until like at least if there's like a few
months in between and they like are dating around and then they find the person that
then they're with that but I guess it really it really depends on the situation but it does
it does kind of scare me if someone's always like in love with a new person yeah because then you're like what's makes hockey
trust their feelings towards you and also like how are you falling actually deeply obsessively
in love with that many people you're obviously like just insane or there's something wrong with
you like how are you doing that that's not real that's like they must be idealizing the person and falling in love with the idea of people versus the actual
person because you can't just continuously fall deeply and obsessively in love with a person every
fucking month like 100 do you think a lot of people do that yeah i think some people it's
i've definitely been with guys that are like that for sure oh you think guys do as
much as women yeah not as much there's different types there's different types of guys like i
have that i have dated personally there's type a and type b type a they are the asshole guys that
i'm obsessed with that give me an inch and i take a mile like they they tell me like that i look
pretty one time and then they like hook up with someone else but i'm like oh but he told me like i was
pretty so like he obviously is in love with me and i that's who i write all my songs about that's
who inspires me and then type b is the guys that are obsessed with me and they treat me so well
and they're so nice but they're just kind of like like they do that to probably every girl that they end up liking like
it's not actually like they're just kind of almost not weak but like kind of weak like they just
like and they let me boss them around like don't do that why are you doing that and also they don't
have their own boundaries well i don't know it's i guess it's your fault in the sense of
well no i don't think it's your fault in the sense of,
well, no, I don't think it's your fault because we're talking about a romantic relationship.
In a romantic relationship,
like you're not their mother or their caretaker, right?
Like their friend or their mom would be like,
hey, you're supposed to like,
don't let her talk to you that way.
Yeah. Right?
But in a relationship,
like you have to have your boundaries,
he has to have his,
and if you're these nice guys do you
think that i saw actually something today like and then we've talked about this before but
like people say oh nice guys finish last and you're last and you're kind of describing a nice
guy but there's got to be something about like an insecurity that they have like kind of like
you point is they're not setting boundaries what's causing them not to send boundaries
is it the fear that like if you if they say no to you
you'll leave but it's it's not even necessarily nice guys because who's to say that like
nice is also subjective it's like people can to your face be so nice and do all these things for
you but they might have their weird ulterior motives or it's based off their own insecurities
or it's just some weird and and it can feel fake when
someone is that's why i'm not into like super romancey gushy gushy gross things like that
because i'm like this is fake like i don't i would never fucking say that to you like stop don't do
that right now like i know you're not whatever so people that do that aren't i don't necessarily
think of them as nice guys and then they're like the guys that are kind of players they can still be nice people like i end up being friends with most of the people that are an asshole
to me when like i i don't really care at the end of the day i'll swear and love more whatever do you
but they can be really really really nice to me and compliment me and be great and they just aren't
the right partner and they don't want to date me and that's that doesn't mean they're not a nice
guy so nice guys finish last. It's like,
yeah,
if you're being weird,
I,
yeah,
I think it's more like,
do you think it's respectful guy?
Like they're not,
they're,
it's like they should replace respectful.
Well,
they shouldn't replace respectful.
Cause like nice guys might finish last because maybe it's not a nice thing
and they're not setting boundaries,
but like the,
the asshole guys,
do you find them while they might still be nice to you in moments? Do you think they're respectful? boundaries, but like the, the asshole guys, do you find them
while they might still be nice to you in moments? Do you think they're respectful? Like, do you
think they, do you feel like their respect towards you? Never a bad time to learn anything. Never.
It's never too late to become an expert in whatever you want to be, whether that's dog
training, whether that's filmmaking, whether that's photography, skateboarding, home design,
the list goes on. And the coolest thing about Masterclass is you're learning from truly the
best. Did I say skateboarding? Well, I mean, talking about Tony Hawk is there to teach you
how to fucking skateboard. How cool is that? Martin Scorsese, one of the greatest film
makers of all time, teaching you how to make film. That is incredible. You have the lovely Robin Roberts.
Let's see, Neil Tyson Degrassi, Anna Winter, Gordon Ramsay, how to cook. Oh my God, this is
amazing. Anyways, I've used it. I've used it long before they were a sponsor of the show. It makes
a great gift. Try and be a master in your class, whatever it is. I highly
recommend you check it out. Get unlimited access to every masterclass. And as a Vile File listener,
you get 50% off an annual membership. Go to masterclass.com slash V-I-A-L-L. That is
masterclass.com slash V-I-A-L-L for 15% off masterclass. I don't know if you know this,
but Madonna is an American icon in more ways than one. She's the embodiment of the American dream.
A woman from humble beginnings who transformed herself into the material girl
and became not only the biggest pop star on the planet,
but a movie star and the world's number one trendsetter.
And an all-new season of Wonder is Even the Rich.
The host tells a rags-to-riches story of how Madonna became the queen of pop.
What makes Madonna remarkable is that she stayed on top for four decades,
four decades, while countless other pop stars came and went.
Listen, a lot of Madonna fans out there, I know I am,
and this sounds so fascinating, so be sure to check it out.
Listen to the latest season of Even the Rich,
The Making of Madonna on Apple Podcasts, Amazon Music,
or you can listen and add free by joining Wondery Plus on the Wondery app.
Wondery, feel the story.
It's weird because, again, it depends on the person,
but whoever, the people that are coming to mind,
they're relatively respectful.
I know if I asked, hey, did you hook up with this girl
or did you do this or whatever,
they'd be honest with me and they usually are but then i think it's it's just more like it's it's weird it's
complicated because they're they generally are nice to me like i wouldn't i wouldn't hang out
with a guy who was like actually being mean to me that's not, I have a little bit of self-respect, but.
Do you not?
Yeah.
I feel like you have a lot.
Yeah.
I have a lot of self-respect.
You downplay yourself a lot. I know what I'm doing.
I know what I'm doing,
basically,
is what I'm saying.
You wrote a song about,
my girlfriend told me
you wrote a song about Logan Paul.
Is that accurate?
Is my information correct?
We don't have to talk about it.
You slouched out.
One song,
10 songs,
who's to count you've read
more than one song uh that's and have you talked to him about that oh i made him a cd for his
birthday with all the songs i wrote about him oh that was very flattering and i yeah no he he's a
he's uh has no emotion so i can do and say whatever I want. And he thinks it's hilarious.
We're still friends. Is that a good thing?
You're still friends?
Yeah.
He has no emotion.
No,
I don't think so.
I think he has,
he's kind of,
uh,
got sympathy down,
but empathy is,
uh,
sympathy,
but not,
he's lacking a little.
Yeah.
You know,
like he knows when to feel bad for people and when to be nice,
but the actual emotions of like,
you don't think
he's like a narcissist do you i'm not i'm not a psychiatrist but i i'm really into psychology
i'm just kidding no but yeah no what it's not called sociopath that's about him so
what what like all right so you're obviously very self-deprecating about like the choices you've
made but you must have learned a ton from this like what have you learned what's the biggest
takeaway from interacting and dating logan paul like what can you say like thanks logan
i learned this because of your nonsense according to him he's like i gave you so much content like
i'm amazing he thinks he's amazing because he gave me so much content like i'm amazing he thinks he's amazing
because he gave me so much content and i i do i say i'm like thank you so much you gave me my some
of my best songs um i really appreciate it and i love also i love all his friends his friends are
the best people ever my i one of his best friends is now my actual best friend i'm like he's i talked
to him every single day he lives in l London. But he and all of his,
one of his friends just called me earlier
and invited me to go to game night tonight.
Like I'm like best friends with all of his friends
and I love them.
So that's great.
I gained a lot of cool relationships.
I feel like I'm better now at navigating
when people are lying to me
or being just like saying shit to say shit.
Like he's the kind of guy that'll like,
like he just likes to fuck with me. like he just likes to fuck with people that's his thing and it's funny it's very entertaining and he'll say things just for the sake of bullshitting and then
you're he kind of expects you to realize that it's not real and you and now and now i'm really
good at gauging that with him because like we're friends. I hang out with him sometimes.
And he will still pull the same bullshit.
And I'm just like, mm-hmm, yeah.
Dope.
How do you spot a liar now?
I mean, you can just tell by people's demeanor.
I just don't let myself get caught up in bullshit anymore.
And not that I ever was really, really bad at seeing when people were fucking with me.
But like, I'm just, I think I'm just really, really good at it.
I also, I like, now I'm kind of bullshitting people more.
So you learn how to bullshit from Logan.
And I don't know if it was from him, but yeah.
Okay.
But at the end of the day, if I wanted him to be honest about something,
I could just ask him and him to be honest about something i could just
ask him and he'll be honest about it but it's fun to just like fuck around and kind of bullshit and
lie to each other do you like do you think it's good do you like being staying friends with like
how am i curious how would you just do you consider him an ex no we didn't date okay no how long you
guys hang out for first time was like a month and then we didn't talk for like a long time.
And then hung out again for like a couple months.
Didn't talk again for a while.
Hung out again for a couple months.
Didn't talk again for a while.
Who started it?
Who started it up?
Did you always initiate?
Did he?
Was it boredom?
Yeah, it was usually just like boredom or like the most recent time that it happened.
It was like i
had just gotten out of something and the night that i i had gotten essentially kind of it wasn't
dating this guy but i like got dumped over text and i was like i had i had seen him for the first
logan for the first time in a long time at a party the night before and so i was like fuck this i'm
gonna go i'm gonna go hang out with him and like whatever so then i just i started up again i don't know if i'm gonna want to put this in but i went to a party with my friend
and i saw him and i went up to him and i said logan i just got dumped and i need you to have
sex with me tonight because i you're the only person that i can hook up with and not feel
anything for and he was like okay let's. And he probably asked for a thank you afterwards.
It was, yeah.
Anyway, I just, I like every time,
I'm the kind of person that if I am hung up on someone
and then something bad happens,
I will go right back to the last person
that made me feel anything
and hook up with them to get over that person.
And then I'll probably get stuck on them again.
And then they'll dump me
and then I'll go back to the other person after you hooked up did
did it work what you hoped would work like did you feel better worse
oh i did not cry about the other guy until i stopped hooking up with him again until you
stopped so you almost hook like it was like it like it like puts my emotions for the other person on pause.
Like, oh, I don't have to deal with it right now.
Cause I'm like doing this little stupid thing that I know I shouldn't be doing.
And then you stopped that and then it all, and then you had to deal with it.
And then I was like, oh God, fuck.
Yeah.
How did you deal with it?
Um, I didn't.
You're still dealing with it.
Yeah.
Well, I mean, it's, it's like not, it wasn't.
We can talk about it.
I'm really good at helping out in these situations.
I mean, I just talk to people that know the guy that did.
It's a complicated story.
But I talk to people that know him and they're like, you dodged a fucking bullet.
Like, don't worry about it.
Does that make you feel better?
Because that happens a lot, right?
Like, I'll have friends that come to me and this happened. And people say that all the time. Like, you dod worry about it. Does that make you feel better? Because that happens a lot, right? Like I'll have friends that come to me and this happened.
And people will say that all the time, like you dodged a bullet.
But unfortunately, that often in that moment doesn't really make that person feel good.
Or does that make you feel good?
Because like, I don't know.
It's a weird thing people always say.
But you're just like, I wanted to be bulletproof.
No, but I know I wouldn't have been happy with this guy.
He like, I know that he already, I already felt like I had to be bulletproof. No, but I know I wouldn't have been happy with this guy. He like, I know that he already,
I already felt like I had to like walk on eggshells with him and like be like
a caretaker.
So I was like, I don't want to,
I don't want to do that at the end of the day.
He was really cool.
But yeah.
And it's just, it's weird when like someone,
so he basically started dating someone else and didn't tell me.
And that's why things ended. And then like having to see that on the internet is like what really gets to you it's
like i don't want to see that please and like you can't escape it like it'll just be in random
places yeah it's uh how how big do you think your ego is my ego yeah i have a big one like just no
no judgment space here like we all i mean we all do
but how do you it's got to be tough like you get a lot of attention you're talented you're good
looking you're on the internet people follow you it's it's it's a bugaboo to try to control our
egos well i will tell you i am very grateful because i was bullied when i was growing up oh
i had i got a nose job when i was 16 i had had a big ass honker in the middle of my fucking face.
And,
uh,
I was,
I was just a tall,
skinny,
lanky,
awkward little girl.
And,
uh,
everyone fucking just hate and not hated me,
but like people were just assholes to me.
I never,
it was really,
really hard for me to fit in.
Um,
and when I started making SoundCloud covers,
like everyone would just make fun of me for that. I started posting original music. Everyone would make fun of me for that. And then it turned from like, it was really really hard for me to fit in um and when i started making soundcloud covers like
everyone would just make fun of me for that i started posting original music everyone make fun
of me for that and then it turned from like oh she's like so weird to oh my god she thinks she's
so cool because she has a song and i'm like okay well i can't fucking learn with you goddamn people
and then it was like when i got a nose job i was like oh she got a fucking nose job it's like well
you guys all told me it was ugly so i got it fixed for you what do you want me to do um so yeah i'm like i feel like i was so insecure for most of my life that once i finally
got confidence and was like okay whatever it took me so many years and then it was like you have to
fake it for a little while and then like being on instagram and everything like i would like
facetune my photos and like try to be cute and then i just recently not in the past like year
or so i think also quarantine really helped me kind of like solidify my confidence i was spending
so much time with myself going back to therapy figuring out everything that's wrong with me
mentally and everything and now i feel like i'm pretty fucking confident like i don't i don't know
i'd say my ego is probably pretty big right now but that's okay but also
like it's not it's not from like a place of like i'm fucking better than everyone it's like i used
to literally hate myself so much and now i don't so now i'm like proud of that so i'm like proud
of not only that but also like learning to be proud of my accomplishments and who i am without
feeling bad about it like not being like oh well i can't be a bitch about how I'm doing this like because other people aren't but it's like I spent
so long not being proud of that and not thinking I was anything great and now I'm doing that so
yeah I was I was bullied in middle school and as a result and I got cool in high school
and then I found like I almost overcompensated overreacted and then i think i
wasn't a bully at all but like i was kind of a dick sometimes and you look back and then
yeah so it's it's a process i also think that our egos are superpowers we just have to learn
they're i don't do you like comic books at all no well yeah it's a superpower that we can't control
okay like imagine like being superman and
not knowing how to control his powers and every time superman got angry his powers would just
pop off and so like he's superman he's great but like he knows how to control his powers
imagine superman being teased and picked on or needing to feel good or having attention. And that,
because our egos can do great things.
It's a motivating thing.
I'm assuming like when you get your heartbroken,
your egos bruised,
you're out there writing music and you're being super creative.
And it's like,
you might see someone,
you know,
who's also in the business.
You're like,
I can do what she's doing.
I can do what he's doing.
I can write like,
that's a great power to have to like,
it's work ethic.
It's challenging.
But like sometimes when like we get hurt and we don't know how to control it our egos will just
like fuck with us or sometimes hurt people around us because you know we'll be sensitive and we'll
say or do things to really like get back on them because we're we're just so butthurt about our or
just we're so hurt with our egos it's um it's a yeah i've decided it's
a superpower i also talk shit a lot about ego a lot like and i like thought about it because i'm
like i feel like i'm giving ego a bad name but like it does so much for me it's it's helped me
uh get over a lot of things people with the biggest egos a lot of times are the most successful
because and also like it can make you kind of like charismatic and shit like because you just have the confidence and
nobody like it's not fun to hang out with someone who's super super like insecure about everything
about themselves and i know that because i was not fun to hang out with when i was like 17
i don't know how i had friends i was so like i would go home crying every time we would go out
and like i there was one night i was crying in my bathtub and
i there was like two inches of water and i was like i'm gonna fucking drown myself and my friends
were like olivia please get out and i was like i had to take me out of my bathtub and then my
neighbor this girl was i'm friends with used to be my neighbor and i put on like a towel and went
walked over to the her house in a towel and then i laid down in the middle of the street and was like i want someone to run me over when i was really really drunk but i'm like why
did they fucking hang out with me when i acted like that like that's crazy that's crazy that's
what friends are for but now now when i get drunk i'm happy because i don't have the the demons of
being insecure um yeah so i don't know i i think that's that's an interesting perspective of saying
it's a superpower yeah some people that i know that have really really big egos are actually like fun to be
around yeah it's just you just have to learn how to control it but then it's like the difference
between someone that just has like a big ego versus someone who like is actually really insecure
and then acts like an arrogant prick just to to overcompate or not. That happens all the time.
Is that still having an ego?
We all have egos.
I mean, but like a big ego.
Well, that would be, you know, well, I think what, yeah,
when you describe it with like someone comes,
like I think the biggest sign of someone's confidence, talking about confidence is the ability.
Like I think from my, I just met met you you seem like a very confident person
because you are so open to talk about your insecurities that takes confidence like it's
how many people do we meet who you'll ask like oh what's an insecurity what's this and they're
like nothing i don't know nothing really bothers me and they'll say something like you know like
my biggest weakness is i'm a perfectionist you you know, shit like that. And it's just like, so full of shit.
And all you see is this kind of like, you know,
they boast and they're constantly like doing things for attention and
validation. And then they never like to talk about their insecurities.
And when they do, it's not, it's not an insecurity that you see.
Like the hardest insecurities we talk
about is ones that we're all aware about like we all see the insecurity everyone knows about it
it's the elephant in the room and then someone's like oh like what's your insecurity they're just
like you know i'm i'm not good at spelling you know and it's just like no one gives a shit you
know like and uh and i think know, our ego sometimes will stop us
from recognizing that and getting that confidence.
I'm like, our egos, again, can give us confidence,
but they also can stop us from showing our confidence
because we're just not able to talk about our insecurities.
And I think like you, for example,
like that's the impression I'm getting from you
is that you might have insecurities,
but you're overall very confident person. Yeah, and I feel like I just had to kind of is that you might have insecurities but you're overall very confident
person yeah and i feel like i just had to kind of learn to talk about my insecurities because
i was like writing about them and putting it on the internet for everyone to see like
it's hard to do yeah i was i was writing songs and about all of this shit that i'm feeling and
that's i can't be like oh actually no i don't feel like that i just wrote it because i wanted to like
like how would i i don't know so i i just wrote it because i wanted to like like how
would i i don't know so i think i just have learned how to talk about it and um be okay with talking
about it also i know that i have a lot of like young girls that look up to me and i when i was
younger and i was on the internet and i would see people like if someone talked about something that
i wasn't secure about it would immediately make me feel so much fucking better about myself so i will if if someone else like is relating to me and i know
that a lot of people do relate to me that's like the number one thing i get like you're so relatable
i relate to your music i relate to what you post on social media whatever so i feel like it's just
a benefit for everyone if i talk about shit because do you ever find that people you have
tried to use you being honest
about your insecurities against you where like you say hey this bothers me or this makes me feel a
certain way and then whether it's like a troll or something um definitely internet trolls but then
it's at that point it's like i mean and i used to really really let that stuff get to me and now
how are you better with that because i feel like it's something we all struggle with and it's all relative like whether you're olivia bryan who has all these
followers or you're like jill down the street who has 600 followers like trolls exist all over the
place well what i realized is like they are who like who are they who the fuck are they like
they have zero followers i know but but you genuinely have to be like also the what i always tell my friends that are like in social media is
like the people that are commenting mean shit on your videos or mean shit on your posts whatever
everyone that i know like all of us normal people out here we wouldn't comment something mean on
someone's post like we just wouldn't like i don't know any single person that would take
their time to go on the internet and comment something mean maybe they'll send it in the
group chat and say look this guy look at this fucking guy but we're not gonna comment take the
time out of our day to comment or message someone and be an asshole like that's that takes a special
kind of person that is so deeply insecure and sad about their own life that they are trying to make
themselves feel better by going on the internet and saying all this shit also they may be the loudest fucking voices because they
won't shut the fuck up and they will just keep going and saying things and whatever and they
probably make multiple accounts when you block them and they're crazy but the majority of people
like what you get a couple hate comments and the rest are nice and then there's besides people just
commenting there's however many people like saw it and just said nothing and probably still liked it you know what i mean like
they're they're the loudest but they're not the majority just because they're the loudest doesn't
mean that they're the most important or or the the thing that everyone agrees with so that you're
right it's just it seems like you have a good handle on it and i've i've even myself have
struggled with it like you and it's especially when they like it when i'm having a bad day and i see something
and it's like just gets me just the right way like it's just they know exactly the right thing
also like i know i'm not supposed to give you any any attention but like it's all i can think about
i used to reply to everyone now i just block i used to reply to everyone and be like well i don't
understand why you would say that about me because whatever kazzy kazzy david in her book and i i'll she's a fred and i'll occasionally
text i'll occasionally text her to remind her just how how like it's one of the best things
she's ever said to and she wrote in her book so she said it to everyone but it's something that's
really helped me and she said uh any response to an internet troll no matter how good it is
is insane yeah and it's so true and i've since having her say that i've had weak moments where
i'm like i know like i know this is a good i could disprove this i know and i've sometimes i've done
it and i but it's true you never feel better because all they want
is the validation of the attention and to know that you saw it even just like they just want to
get in your head and also especially like since so i used to for like a really long time i was
like i would not tell anyone that my songs were about logan or that i ever talked to logan because
i was so scared he has so many crazy fucking people find People find out everything. And even if they don't know exactly what's happening,
they like think they do because they,
they like are spies.
And a lot of the guys that I've like,
not like the dated and not like actually dated,
but dated have fan bases like that.
And it's always terrified me.
So I never wanted to talk about it.
But then ever since I started like,
just being like,
okay,
whatever everyone,
everyone fucking knew everyone knew I went on his podcast and still
didn't say that it was about him we like pretended like it wasn't but he knew yes he knew i don't
know him at all but i feel like he's the type of guy who would want people to know you wrote a song
about he's never he's never cared he's never cared it was always like me being like no please don't
post that please don't tell anyone whatever like i't tell anyone, whatever. Like I never want anyone to know. And then now that I do talk about it, I get so many comments every single day.
Like you just want to use him for his clout and you're a fucking liar.
And then they'll like DM me and be like, you shouldn't talk to him ever again.
Like he has the craziest internet troll fans.
And ever since I started talking about it, I've been dealing with,
that's been the craziest shit I've been dealing with is like those people.
But it's, it's kind of taught me to like ignore it because they just there's no like there's just it's funny to me now i just like look
at them and i laugh do you think you will continue to write songs about men you date yeah fuck yeah
okay of course and if a guy goes on a date with you and and he's like hey are you gonna write a
song about me if it doesn't go well will you be like fuck yeah well it don't flatter yourself it's like i it takes a lot for me to actually write
a song about someone like i've dated fully dated guys and never written a song really about them
so i could picture some sort of narcissistic guy just be like i just want to write a song
and just do terrible fucking shit and just be like i'm just trying to push your buttons no it takes it
takes a really special kind of guy to to get me to write especially because like i i have a tattoo
this is a tally mark of the three guys that i've written my songs about um there's only been three
and i've obviously there's been a lot more than that in and out of my life but those three i wrote
like fucking like 20 songs about each of them
you know what i mean like i i go through it's like each era is like inspired by a different
person which is so like ew i hate that i'm like relying on like like misfortune in relationships
to inspire me but that it's working right now whatever i don't give a fuck failure is a great
i mean i've you know people always like why do you give relationship advice or whatever like but it's working right now. Whatever. I don't give a fuck. Failure is a great, I mean, I've,
you know,
people always like,
why do you give relationship advice or whatever?
Like,
and I was just like,
I don't know.
I've been through the fucking ringer.
I have learned I've,
uh, you make mistakes and like you do it through,
through songs.
And I always,
I always get it really.
I don't want,
I personally don't want to hear from people,
whether it's through music or advice or whatever.
When someone says to me, like like i've always had it good i've only been in this one relationship and it's perfect perfect
yeah i don't really have anything like you know what you should do here's the advice i have for
you they're just like get it right you date someone perfect how is that helpful like yeah um
you can always learn from, from those things.
One,
when you ever,
when you find love,
do you,
if,
if you find love,
how do you envision it's going to be?
Like,
how do you want to be at,
like,
what's your dream scenario?
I am more worried that I will not find someone that I want to spend the rest of my life with.
I am very worried about that because I
am crazy. I've had that fear. I think it's a relatable fear, right? Is it not a relatable fear?
Yeah, totally. I think it's like a universal fear. Yeah. For me, I don't know if you relate,
like I've, you know, I've been in love. I had my heart broken, you know, like my first relationship. And it was so like, you know, it was the rom-com stuff.
And for me to get over that, I had to like learn and like be analytical and process.
And at least a concern for me was, and then I went on a TV show and, you know, it's all dramatized.
Obviously, the best way to find love is to go on The Bachelor.
Of course, that's why everyone goes on you go on and you say i am here because i am ready for marriage
i was truly afraid after all that that i'll never i'll never know like i thought my fear was because
if the surefire way to find love didn't work for you the bachelor exactly what will work how will
work but i was what i was like i always like would meet a bunch of a bunch like kind of way you described i meet all these nice
girls hot girls and like have these good dates and sometimes you hook up and sometimes you don't
and it's like it's cool like i don't but i don't know if i love you like you know i want to be
fucking obsessed with someone that it makes me want to die and i want to be able to write so
many songs about them and i want to i want to go on many songs about them. And I want to go on adventures. I want to travel the world.
I want, I need someone to be at least as successful,
if not more successful than me
because men get really emasculated in relationships,
whether they will admit it or not.
They feel uncomfortable
if the girl is like doing better than them.
And that success is, you you know it's relative but i want
someone that is at least like has the same kind of mindset with me as me about work and success
and life goals and all that stuff could you fall in love with let's say
the best high school teacher in america loves his job passion teacher of the year award he's
crushing it you know financially obviously teachers we know are underpaid and sometimes
underappreciated but he's the fucking best he's like coach the year he's i mean if could you do
that or does it need to be someone like no if we were really compatible and like that's fine and as long as he's not like insecure and emasculated by the fact that i'm going on tour
and doing all these crazy things and hanging out with random hot people all the time and as long
as he's secure like i don't care what he just has to relate yeah and that's what i've realized a lot
of the time is guys that aren't in the entertainment industry don't get it they don't understand like
i have a
lot of guy friends that people might think are like really hot guys but i'm not attracted to
them at all and they are not anything that someone i'm dating should worry about but like being in
this world is like probably very it's just unknown to a lot of people so i've had more success with
people that are in the entertainment industry and understand my life i guess do you
like um like when you said the confident guys how what is a confident guy to you and
do you like guys who are protective and can they be both do they have to be
confident to be protective or can a guy be overprotective while showing an insecurity does
that make sense i i mean there's definitely like a level of of protectiveness that you want like
if someone's you know being an asshole you want them to like come to your come to your rescue the
classic thing but uh there's definitely like if i'm doing something that's totally fine and normal
and they're getting like overprotective about it then that's that's an insecurity thing that's like a trust problem so i don't know um it just really i i really don't ever
want to say like this is what i want out of a relationship or like this is the kind of person
that i want because i don't know until i meet someone i've definitely had a type um i do you
have a physical type or personality like both i like like not like super
super muscular guys but like tall pretty muscular like like guys that really like to work out and
play sports or whatever um athletic athletic guys yeah and then but i've just dated a lot of like
youtubers and internet boys and they hooked up with a lot of internet boys are they generally athletic yeah okay my friends make fun of me so much like it's insane
they make like i i'm the butt of every joke but yeah that's my type so i i would love to move on
from that i'm not saying like i only want to date those kinds of guys but i just i i just my main
thing is i just want to be obsessed with someone because it has to inspire
me. But what if we talk, what if I told you, cause we've learned this on the show that sometimes the
initial spark is a red flag and not necessarily, but how do you, how do you, how you how are we gonna get you to know the and i don't
know the i don't necessarily have an answer because i love that i want to be i i'm i'm
obsessed with my girlfriend i'm 100 obsessed but at the same time uh like i definitely didn't feel
that spark at first probably because i was kind of void if i don't feel the spark i will not hang out with
them again like i just don't i don't want to waste my time and i don't i mean so you have to be
obsessed right away but i'm also like when i go on dates and stuff like i'm i'm really really
sarcastic i'm i like to kind of fuck with people and like feel them out a little bit and like say
really crazy things to see if they laugh or if they're uncomfortable um you're like yeah so i it doesn't necessarily have to be like that crazy spark but like i have to know that
they're going to be the kind of person that i can get along with and be weird and psychotic with
so and i i i don't have like different personalities but there's a lot of like
i can be really really emotional but i can
also be just i just want to have fun a lot of the time and i need someone that can kind of handle
both of those things and i'd like to feel people out and a lot of times i'll they just aren't we're
not vibing like that and i'm not gonna hang out with them again so but you might not be obsessed
right away i might not be obsessed right away but they have to at
least have that thing it's like that thing that you can't i've heard that someday and like you
know 10 years from now or five years from now or three years when you're gonna whoever you end up
with you're you'll be surprised you'll be like i never would have thought do you like that idea
or not you don't like that because i don't want to end up with someone boring and lame that i'm
like well no they'll be exciting you don't know who idea. Because I don't want to end up with someone boring and lame that I'm like. Well, no, they'll be exciting.
Who said anything about boring and lame?
Because I just said I want someone exciting.
And you're saying that I'm not going to have that because it's going to be something I don't expect.
You're going to end up with someone really boring.
Going to be an accountant.
I did not say that.
For the record, I did not say that.
No.
For example, I used to always date women who are kind of like what you're describing.
Like I love to challenge. Right. So I would equate that to right off the bat.
Just, you know, I'd love those little games and they would kind of challenge me.
And I kind of took that as the challenge, so to speak.
And so much that I didn't realize at the time.
But like their challenge was kind of, you know,
like challenging my ego.
And so then I would get attracted to the challenge,
so to speak, rather than them.
And then like, for example, like Natalie,
she never did that.
You know, it wasn't boring at all, but.
But it wasn't the like stupid games.
It wasn't the games.
And the challenge as the relationship evolved was more like just kind of conversations and then when that when she would challenge me
about something it's like either this bothers me or i think you could i don't like how you did that
etc etc it became less of a competition and more of like i got i got felt better about it i don't
know but it was just it was i just saw it differently yeah you know and i
and i had to date like the same girl 20 different times like you know like we all like we do that
like it's normal and you always tell ourselves like no this one's different and everyone's like
no it's like it's a different hair color you're like and i wouldn't even date different hair colors it would be I'll be brunettes
a couple blondes
alright this has been great
Olivia before we let you go are you done to play a fun
game called do you know me sure
don't
obviously so excited
I appreciate the low energy
it's really simple it's called
do you know me or I'm gonna ask I'm gonna ask you I appreciate the low energy. It's really simple. It's called Do You Know Me? I already said that.
I'm going to ask you questions.
Okay.
Has Olivia done this?
Has Olivia ever thought this, done this?
Don't answer right away.
We're going to guess.
Oh, okay.
If we know you.
Okay.
Hence the name.
Simply yes or no questions.
Answers are fine.
Anecdotal stories about your
answers are welcomed but not expected okay question number one has olivia ever paid
for a psychic reading yes yes 100 percent
um it's so funny all of my friends
are going to
the same psychic
right now
and they're all
one of my friends
paid her $700
to be her like
psychic fourth a month
and like
but I haven't
gone to her
because I'm scared
I'm so scared
that I'm gonna go
to a psychic
and they're gonna
tell me
exactly everything
that I don't wanna hear
like he's not
the guy for you
stop talking to him
you're not gonna
end up with him
you are the worst
dater ever you need to do this and I'm like i don't want to hear it i'm having my little stupid fun
right now so i don't believe in psychics yeah to an extent i think there are definitely people
that are like scammers out there but i but i've had some experiences with people that are and
people that i know have had really crazy experiences where stuff is real um and sometimes
i feel like i'm a little psychic like i think I have, I just am like intuitive.
And I'd actually did a YouTube video
with these girls, the psychic twins.
They are these, they're like in their 50s or 60s, I think.
And they like live together still and they're twins.
And they're like, I actually,
like I believed everything that they said to me
and they'd predicted I was gonna play Coachella.
And I didn't, Coachella didn't happen, but like I believed everything that they said to me. And they predicted I was going to play Coachella. And Coachella didn't happen.
But, like, I did get booked for it.
Are they going to book you back?
I'm not allowed to speak on the subject.
Congrats.
Shut up.
There you go.
I should not confirm anything.
I cannot confirm or deny anything.
But they predicted a lot of stuff.
And I really was like, okay, hell yeah. Max max you were there right yeah with them they um i walked into the room and i had just
lost one of my best friends and she like stopped olivia in the middle and looked at me and was like
um somebody's coming for you like did you just lose something in a car accident and i was like
i can't do this i'm gonna start crying here.
No,
like I believe in that shit.
And they told me that they think I have like mild psychic abilities.
And I was like,
I believe you.
When I was a little kid,
I literally thought I had superpowers.
I thought I was like a fairy and a mermaid.
I just got a fairy and a mermaid tattooed on me because of my weird obsession as a child.
And I thought I was psychic.
I was like,
I'm literally psychic.
My grandma's like into astrology and I'm really into astrology.
So I just like think that I have this weird like intuitive thing.
Okay.
But yes, I have.
I'm afraid of psychics.
I'm skeptical, but I also, there's a part of me.
That they're going to tell you some crazy shit.
I don't want to have you go down a rabbit hole because I know you said you think about death.
But like, do you want to know?
No.
Neither do I.
No.
Fuck no. Do you want to know? I like the mystery. Yeah. I don't want to know no either do i no fuck no do you want to know i like the mystery yeah i don't want
to know i'd be too afraid has olivia ever quit a job yes i don't think so
like just for clarification she's like i quit yeah like i think there's gotta be some like
situation where you're like growing up and like working at the mall or something like that when
you're growing up i don't mean like resign you're like i'm out of here like quit like when you
walked into work you weren't expecting on quitting but you're like fuck this i'm out
like then she'd have every job she's ever had before this. I see the difference.
Resigning versus quitting.
I think once when you were younger.
Yeah, like a mall job.
I'm going to say no.
She saw it through.
She finished the shift, so to speak.
Well, plot twist.
I've never had a job.
I started music when I was 15, so this is my first job. I was an intern in a dress shop when I was 15 so this is my first job
I was an intern in a dress shop when I was 8
and I used to seam rip dresses
that's a job
but I didn't get paid and I was 8
and I didn't quit
it is wild to me
whether it's you or other musicians
when you hear
you're writing songs and music that came it's like it's
i couldn't it's really awesome it's pretty random like when your your songs that you've come out and
like i could i was excited when i learned how to ride a bike i was excited when i learned how to
ride a bike too well then you had like a platinum album and i was like running track um all right question number three would olivia rather
give up social media or give up television
you know let's say like on a on a personal level like not like because obviously social
media is important for your like brand yeah like your entertainment yeah thank you for yeah so would you wait let's let's say that like because my career is on social media is important for your like brand yeah like your entertainment yeah thank you for
yeah so would you wait let's let's say that like because my career is on social media like someone
else could run and post for me but i just wouldn't be able to be on your career still thrives okay so
that's the question but like it's sunday night you're trying to avoid the monday scaries and
you just want to be entertained and you could add to you know tiktok or i'm gonna say you'd
rather give up social media i agree i was gonna say that but then you know tiktok or i'm gonna say you'd rather give up social media
i agree i was gonna say that but then you said tiktok and i was like no everybody loves tiktok
so i understand that but i feel like she's talked about mental health and things like that and i
know it fucks my mental health up and you know like i watched uh sex and life last night and
while it was like weird i still went to bed fine like i've gone on tikt night and while it was like weird, I still went to bed fine.
Like I've gone on TikTok and it's just like fucked up my sleep.
I don't know.
That's just me.
I think she'd give up social.
Yeah, I would give up social media.
But I,
only because like I wish that I could.
Like I wish I could so badly
and I love TV.
Like I based my last project
based on like TV and movies.
Like it's like, it's called Episodes and it's like about Like I based my last project based on like TV and movies. Like it's like,
it's called episodes
and it's like about,
I don't know,
each song like has like a genre
of like a TV show or movie
that I like relate it to
and like production wise.
Anyway,
so I'm like,
love,
love,
love TV
and stupid TV shows.
What's your favorite shows?
Right now I'm rewatching Modern Family
which is absolutely elite.
So well written.
The characters are incredible.
New Girl,
fucking love that show. I've watched so many tv shows i'm definitely more into tv shows and movies because
i i like to binge like i would rather watch like eight seasons or something than like one movie
and it's over um vampire diaries i watched when i was younger i'm obsessed with that show gossip
girl um i just re-watched Girl I've seen it like four times
it's crazy
there's literally
so many shows I love
I can't even
Nathan For You
Nathan For You
is the best
like stupid shit
like the Eric Andre
show is fun to watch
when I'm just like
his follow through
is amazing
dude every
like there's
yeah
I couldn't go up to you
ever
okay
has Olivia ever spent over $1,000 at Target in one shot?
I mean, there's an option for $100 here.
I'm like, you could blink and spend $100 at Target.
Yeah, for real.
I'm going to say $500.
I mean, $1,000, sorry.
Have you gone to Target?
I'm not just going to go to Target.
And you walked out $1,000 later. She's thinking about it. I you gone to Target? I'm not just going to go to Target. And you walked out a thousand dollars later.
She's thinking about it.
I don't even know if I...
No.
I don't remember.
No.
Yeah, I don't...
I wouldn't remember.
Interesting.
Amanda picked these questions, by the way.
I didn't pick these questions.
Well, I just...
There's like a...
This kind of like could be described
as potentially like sexist
because like, can Olivia name six NFL teams?
Like as a guy, I don't,
it's what a prayer for like,
I don't, I make no assumptions
on your interest in sports or lack thereof.
Yeah.
Can Olivia name six NFL teams?
Before you answer. six NFL teams for your answer six NFL teams she's from Napa let's say yes sure yeah I have so many friends in the NFL of course I'm I know like three of them. We're going to need you to confirm.
49ers, the Raiders, the Chargers, the Giants.
Rattling them off.
All right.
Thank you.
You can keep going.
The Buccaneers.
Yeah.
Steelers.
That's six.
Does Olivia know her Uber rating and what is it?
No.
I think Olivia's friends have ruined her Uber rating.
I think you have like a medium low.
It's always the friends.
Dude.
My friend, I bought, I got, so my friend Kelsey's banned from Uber because she was using her grandma's credit card by accident.
She was on her like family account. She didn't realize that it was connected to using her grandma's credit card by accident. Like she, it was, she was on her like family account.
She didn't realize that it was connected to like her grandma's credit card and her grandma
didn't know that she was using it.
So she reported it as all like fraud.
So then Kelsey's account got banned anyway.
So she had to use my Uber account and she was at a gay bar with my friend and she takes
a drink out with her and goes and sits in the Uber with the drink,
spills it everywhere.
The Uber was like, and of course it's on my account.
It's like, Olivia brought alcohol into my car and spilled it everywhere.
I'm like, oh, I didn't do that.
And then I had to like.
You would think Uber would come up with something to like, like your response.
Like, you know, sometimes you might call an Uber for someone and then that's all on you.
But also, but.
Here's the thing.
I had an Uber account that got hacked
i can't use uber anymore because it's linked with my phone number so unless i get a new phone number
i've not been able to call it actually i can't get to where now either because they won't let
me update my credit card information so i'm stuck with lyft it's wandering aimlessly oh i learned this today don't ever plug your phone in with their chargers and
don't ever put your phone on like one of those chargers because it's super easy for anyone
to buy the technology where it goes both ways they can download all your information off your phone just fun fact so don't ever i always
do that because my phone's like always dying so do i which is why i like just psa for everyone
and and you especially delete everything um yeah don't ever use an uber charger they're probably
mostly fine but they're it's becoming a bigger bigger scam i found out today was someone who knows what they're talking about and if someone don't let someone put their
phone on top of your phone because they can that there's technology that allow them to download
your data all your whole phone i don't like i don't even want to know these things like i would
just rather be ignorant in life and just or just don't charge your phone get a middle middle mofe get one of
those like portable chargers ugly i used to have one has olivia ever lived alone i don't even know
if she lives alone now um yeah she lives she's lived alone she's a rock star like she's had to
be independent i don't think so i think family or friends or dudes i've never lived with a dude
well gay dude my best friend drew but never with with a dude. Well, gay dude, my best friend Drew,
but never with like a guy like that.
Like that I was dating or anything.
Yeah, I've never lived alone technically.
I just bought a house,
but my friend Quinn is still like
kind of living with me right now.
So I'm gonna hopefully live alone soon.
Not like that I'm kicking her out,
but like I will live alone in that house at some point.
Living alone is the best.
I didn't live alone.
I always had good roommates and I was kind of afraid to live alone.
And then,
and then my girlfriend and I broke up and I was kind of like,
Oh,
what's this going to be like?
And like two days in,
I was like,
this is awesome.
Like there's no,
are you guys watching this or can I do this?
You're just so freeing.
For me, I've always like, for some reason,
wanted my friends to live with me
and not pay as much money.
So like I'll pay like double what all of them are paying combined
and get the master bedroom.
And then I don't feel like I have to like ask them
before I do.
I mean, it fits something like about with their stuff,
but everything else, it's like,
this is my house.
So like I can do whatever I want.
So then it was like vibes i don't have
to and then it was i was always living with my best friends i've definitely had like drama
with roommates before and stuff but i'm scared to live alone because i i self-isolate like i'm
either the life of the party and like love partying and so much fun or like i will literally not want
to talk to anyone not want to leave my house not want to hang out with anyone and not in like a
not even like oh i'm really depressed it's just like i like to be at home and i like to be alone but my friend quinn who's living with me right now she like we like
cross paths every once in a while but like i like it's basically like i live alone like i walk around
the house naked and play my music really loud and all that stuff so are you an ambivert introvert
extrovert i'm an extroverted introvert in what way like i love socializing in the right settings sure um but
if it's not the right setting i literally can't be there and i always need to recharge at home
like i always have to have my alone time i like to be alone like if i'm with people all day i won't
also want to go out that night like i'll i need to be alone and then i'll go and like have my
little moment and then i really that's like right right you're right in the middle my mom
told me it was called extrovert introvert but whatever it's ambivert like ambidextrous like
you're both you know whatever you're you're well your mom's right final question again amanda
picked this out has olivia ever been streaking no but you're like okay well let me what no not in no not in your house it has to be like we're going
streaking and like i feel like she's flashed someone i didn't say flash that's not the question
i feel like who hasn't done that my answer is has not
gone streaking but certainly has flash well like who goes streaking anymore like i've definitely
like gone skinny dipping me and my friends have all jumped in my pool naked holding hands and
we've like i like have been at parties with my friends and like accidentally shown everyone my non-existent boobs like it's
i don't know it's i'm i'm i'm like my friends know me as the person that's always naked
so is that what's your policy on nudes given when the dating situation are like if i feel like
sitting well i will but don't fucking ask for one okay no also like yeah one time when i was in high school i accidentally posted an aspect on
my story that i meant to send to a guy i was like 15 child porn wow so bad we learned from
lala that you should watermark your nudes and that's probably maybe the greatest thing i learned
watermark she watermarks her nudes so she'll take a nude like this i'm feeling good i'm sending
it to my guy and she'll put his name in a watermark oh so know who so like if it ever gets
out she fucking knows who did it and like yeah it's fucking genius no no i accidentally posted
it on my snapchat story it was my own goddamn fault whenever she said that i just i i it's the
greatest it's the smartest thing ever and i'm sure there's like an app you just get like a watermark app and just slap it on literally
just put like gets any any app that you can put text on a photo you just make it really small
if you like chad you did this uh olivia thanks so much for coming so much fun uh obviously a lot
of people know where they can find you on social but for those who don't where can they follow you and all the things social uh your music where can they listen obviously
spotify things like that let them know yeah music i think is on pretty much everything you can listen
to music on um all my socials are just my instagram is olivia o'brien my twitter is olivia g o'brien
and my tiktok is also olivia g o'brien i think if you just look up my name it should come up
it's amazing music.
I don't know if you guys haven't heard it.
You should check it out.
It's really good.
I don't bullshit people.
You're a very talented musician,
and I hope to see more of your music out there
as you meet more guys and get in situations
that help you be creative.
If you know anyone that you think I would like,
let me know, and maybe set me up so I can write some songs.
I'm lacking inspiration right now.
I don't know if I have anyone.
I'm a matchmaker.
What's that?
I'm a professional matchmaker.
You're a professional matchmaker.
Okay, cool.
Yeah, but when you meet them
and then you're done writing songs,
you can come to me on like an Ask Nick episode
and you can be like, this is what happened.
And I'll be like, yeah, don't worry about it.
I'll explain why you should just get over it.
Okay, great. And then we'll be like a team. what happened. And I'll be like, yeah, don't worry about it. I'll explain why you should just get over it. Okay, great.
And then we'll be like a team.
Thanks so much.
I really appreciate it.
Thanks, guys, for listening.
Don't forget to send in your questions
at asknickatcastmedia.com,
cast with a K for Ask Nick episodes.
And we will see you back on Monday.
Thanks.