The Ben and Ashley I Almost Famous Podcast - Do Men Want You To Pick Up The Check?
Episode Date: March 21, 2026Resident real guy, Mr. Right is answering more of your questions! He’s giving you his brutally honest answers on how men feel when women make more money in the relationship and so...me key tips on what men like to see in online dating profiles! Email us at: IDOPOD@iheartradio.com or call us at 844-4-I Do Pod (844-443-6763)Follow I Do, Part 2 on Instagram and TikTokSee omnystudio.com/listener for privacy information.
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I do part two.
I'm one of your mentors, Mr. Wright.
And I'm here to continue answering some of those questions that we got last week.
So let's dive right into some of those voicemails and emails asking about dating in Chapter 2.
Hi, I'm calling in for the hotline questions.
This is going to be an anonymous question.
If I've been talking to a guy for almost a year, we text before, we have great
chemistry, but he's never planned a real date. Am I being patient or am I being delusional?
Let me know. Well, Anonymous, I'm going to have to say it's been a year and you haven't planned a
real date. I'm thinking there might be some issues there. I'm not saying you're being delusional
because the heart wants what their heart wants, but I just, I think, you know, much quicker
than a year, there should be some momentum there. There should be momentum in the relationship.
There should be progress. And a year's a long time to wait. So,
So, gosh, I can't think of a situation in which this makes a lot of sense to keep pursuing.
So I would put you kind of more, in your words, in your words, not mine, in the delusional category to think that this is going to work out.
Now, Anonymous, this sounds like it could be a long distance relationship.
So maybe you're dating an astronaut.
You know, he's been out of the country, out of the orbit for a while and he can't do anything.
but maybe, you know, if it is long distance and not an astronaut, but if it is long distance,
and that's the reason that a real date hasn't been established, I think this might be some time,
you know, a time frame should be put on this and start building to something, you know,
towards something and put it on the calendar. And if the person on the other end kind of box at that,
then I think that you could probably answer that question and not waste any more time if it isn't going anywhere.
Now, I think if you are going to end this with this person, I think there should be some wrap-up.
There should be some conclusion to it. I don't want to think you should just leave it hanging.
You know, I think you should definitely say, you know, it's been amazing, you know, talking to you over this last year,
but it doesn't look as though we're really making any progress.
You know, I really wish this could have worked out, but I'm looking for something more.
And so I think you can take some responsibility for yourself because, you know, you haven't pressed the issue to the point where something's happened.
So take some responsibility in it.
Don't just put it on the other person.
And then maybe, you know, maybe, you know, that would push that other person to make a bigger
effort to say, oh my gosh, I do not want to lose you.
I'm going to take a flight out.
I'm going to drive out to see you or let's meet somewhere.
So don't just, you know, don't just ghost them.
That's the worst.
But give an opportunity for it to be made right.
And, you know, maybe it doesn't, but maybe it does.
That was a great, great question.
I got another email here coming in from.
Kathy, she says that she's been dating a man that she met through a mutual friend for eight months.
I really like where our relationship is going, but I want to talk about finances and don't know how to bring it up.
I think I make more money than him.
Do guys care about that stuff when we're in our 50s?
My ex-husband was terrible with money, and I need to be with someone who isn't like that again.
All right, Kathy, this is one of the biggest deltas between a first relationship, a first marriage, and a second marriage.
The first marriage, you're just starting off, you know, you might have made more money than your ex, but like, you know, it's kind of a horse race.
Who knows where it's going to go because you're starting off, you're young, you're building your life.
In this second chapter, in this second go-round, if you think that this might be the man of your second dreams, I think that it is important.
to make sure that everything is out on the table.
You know, past, you know, history with other relationships,
all these sorts of criminal records.
And I think that finances are right there with those topics.
I think it's just as important.
You want to make sure that there is no confusion
because maybe it isn't a big deal at all.
But if you don't know, the not knowing is going to eat at you,
especially if you're bringing it up right now,
it is going to eat at you.
And, you know, if I was a good thing,
guy on the other side, you know, maybe, you know, I'd be inspired that my partner is doing better
than I am. And I hope that you would be with somebody that would not be jealous of you,
that would want to be as successful as possible. So this might be a great way to figure out
what kind of guy this is. So don't be scared, especially if, you know, if you guys are in similar
situations, he should expect that because, you know, that's just one of the ways that you go and
avoid a landmine down the road.
Now, what does Mr. Wright think about how guys feel about the woman making more money?
I think if he's a good guy, he would be inspired by that.
I think that, you know, you don't want a guy that's going to be, you know, kind of a gold digger going the other direction.
But I think that guys might feel an initial intimidation by it.
But really, if you've got a good guy, he wants to say, oh, God, this woman has been accomplished.
She's done things.
She's, you know, she's smart with her money.
works hard, whatever the case may be.
But I don't think guys are going to be intimidated by that.
And if so, I think that might be a red flag.
And Kathy, I'm going to let you know right now that guys talk about finances, about their dates,
you know, the women they're dating, all that sort of stuff.
That does come up.
Usually what the caution is, is this person dating you for your money?
Are they a gold digger?
So it's usually that direction.
Now, conversely, if, you know, if the woman,
you know, is successful or independently wealthy, able to take care of herself, that's usually
something to brag about. And so, you know, the joke is, you know, I'll be able to golf all I want
because, you know, my new wife, girlfriend, person I'm dating is going to take care of me.
So usually when we're talking about finances between guys, we're making sure that the other guy
isn't getting taken for, you know, and someone dating him just for his money. But if it's the other way
around, that's usually a pretty cool thing. So taking Kathy's email a little bit further,
you know, there are situations in Chapter 2 and, you know, guys are now dating a divorcee,
and their previous lifestyle might have been extremely extravagant. Now, they might have gotten
a big settlement, they might have gotten a bunch of money, they might be a widower, all sorts of
situations. And I think the guy has to be mindful of, are they going to be able to keep up?
are they going to be able to provide or keep up with what the, you know, what the woman is expecting?
So I think, you know, in that conversation about finances, I think there's a big conversation about
expectations as well. And, you know, in chapter two, I mean, love is so important. Love is so
important. Compatibility is also equally important. And I think that's where in chapter two,
really finances do start to play into it. And I think that that is part of a conversation.
that needs to be had before you have kind of these false expectations and find yourself all of a sudden,
wait a second. Why didn't we talk about this earlier? This was so obvious. And that's, you know,
this is really a chapter two issue that doesn't come up in chapter one. In chapter one, you know,
you're thinking we're going to spend the rest of our lives together. We're going to build towards a
common goal. In chapter two, it's like, yeah, I'm kind of, we've kind of done a lot of that stuff
independently, do our lives merge? And that includes finances. That includes lifestyle. That includes
vacations. All those sorts of things. Those have to mesh as well. All right, Kathy, now you brought up,
you know, kind of a hornet's nest. Now, if we're talking about finances and we've got to talk about
debt. We've got to talk about things like leverage and credit scores. And, you know,
when you're bringing on a partner in chapter two, you've got to make sure you know what you're getting.
It's just like investing in a company a little bit. You want to make sure.
that the balance sheet works. And, I mean, there's always mitigating circumstances. I mean,
maybe the guy just got taken to the cleaners by his ex-wife, the settlement, child support,
all these sort of things. So there could be mitigating circumstances here. So I don't want to just
make a blanket statement. But I do think you need to be careful if one or other is coming into
the relationship. It can be man or woman is coming in with a bunch of debt. It's coming in with a
bunch of credit cards they can't pay off, are coming in and they're not employed, or are living
a lifestyle that is obviously outside of their means. Those are things to be very, very mindful of
because it doesn't get better. It gets worse. And if you are coming into it and you're going to be
the one expected to bridge that gap, you've got to be ready to bridge that gap all the way and
continue to bridge that gap if it's a lifestyle thing. So this is probably,
be the least romantic thing we'll ever talk about, you know, on this podcast. But there is,
you know, there's credit scores and debt. Those things do mean a lot, especially in Chapter 2.
I mean, if this is a topic that is compelling to people, I would say bring in those questions,
or there's voicemails, emails, and we can talk about some of the less romantic parts about
relationships, and, you know, especially in Chapter 2. What are the things to be mindful of? What are the things
that guys and girls should be looking for aside from just that spark. Sparks are important.
Don't get me wrong. But as you get into chapter two, you get in a different phase of your life,
you know, you're thinking about your security, your safety, you're thinking about maybe your kids,
you know, and where they are in their lives. So there are parts of this chapter two, this next
phase of your life that have to be considered that are just really not considered in chapter one.
Getting ready for a game means being ready for anything.
Like packing a spare stick.
I like to be prepared.
That's why I remember, 988, Canada's suicide crisis helpline.
It's good to know, just in case.
Anyone can call or text for free confidential support from a train responder anytime.
988 suicide crisis helpline is funded by the government in Canada.
I'm Nancy Glass, host of the Burden of Guilt Season 2 podcast.
This is a story about a horrendous lie.
that destroyed two families.
Late one night, Bobby Gumpright
became the victim of a random crime.
He pulls the gun, tells me to lie down on the ground.
He identified Tremaine Hudson as the perpetrator.
Germain was sentenced to 99 years.
I'm like, Lord, this can't be real.
I thought it was a mistaken identity.
The best lie is partial truth.
For 22 years, only two people knew the truth
until a confession changed everything.
I was a monster.
Listen to Burden of Guilt Season 2 on the IHeart Radio app,
Apple Podcasts, or wherever you get your podcasts.
Hey there, this is Josh from Stuff You Should Know
with a message that could change your life.
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Well, great question, Kathy.
And, you know, that got us on all kinds of tangents.
And let's get it centered here with our next voicemail.
Hey, it's Emily.
I'm in my 40s and just thinking about getting onto dating apps for the very first time.
It's so scary.
Can you tell me what we should be putting on our profile that won't make you just, like, swipe by immediately?
Like, what are the top things that men want to?
to see when they see these profiles. Thank you so much for your help. All right. This is a great question.
Now, Mr. Wright, this is what I feel. There have three things have changed the trajectory of dating
in mankind. It's been alcohol, deodorant, and social media. There is nothing that has been
more responsible for hooking people up than those three things. Unfortunately, the third part,
The social media part, the profiles, what do you put on there?
I mean, there is so much fluff out there.
There is so much filter and fluff, which is fine.
And it's great for likes and clicks and all that kind of stuff and follows.
But if you're at that point in your life where you're trying to, you know, find somebody through social media or even a dating app, what should you put on there?
I would say put on the truth.
I mean, you can put some fluff pictures.
you can put some filter pictures,
but if you want that first date to go to a second and a third and a fourth
and whatever else comes after that,
you don't want to be selling a false bill of goods.
And if you're into hiking, then put some hiking photos in there.
If you're not into hiking, don't put hiking photos in there.
Don't put outdoorsy photos in there.
Be honest about the sort of guy that you're trying to attract,
not just for the first time, but for the first 10 times.
And so, of course, you can show pictures of what,
you look like in your best of best, but also put a picture in there when you've just finished a
marathon or when you've just finished a hard day or you're at the beat, like mix it up, I guess is
what I'm trying to say. If there's 10 glam shots in a row, that might attract the wrong type of guy.
And what I mean by a wrong type of guy is a guy that's maybe not getting the full picture of who
you are. And so it's tough to say because it's not going to give you the likes and the follows and
whatever else if it's just bikini picture after glam picture after prom picture. But an honest
profile, an honest set of pictures, I think is going to attract the right type of guy that you're
going to eventually be looking for. Now, I'll say for guys, you know, for your profiles, be honest.
You know, make sure that you're not, you know, portraying yourself to be six foot five when you're
five foot five. There's nothing wrong with being five foot five. There is something wrong at showing up
for a date with a girl that thinks you're six foot five and you're five foot five that's lying.
So just be honest about it.
You can, you know, you don't have to be obvious about it, but just don't, don't lie.
Don't, don't be fake.
You know, if, you know, if you, if every hat or a picture that you have has a hat in it,
then they're probably trying to hide something.
Don't need to hide it.
Be honest, because you don't want to end up at that first date and think you're going to
fool them forever.
So be honest.
I think that posting pictures with your friends is important
because I think a lot of times girls are looking at profiles and saying,
who does he have friends to begin with?
Are they all hanging out watching video games,
smoking pot and eating popcorn?
Or are they going out and doing things?
Are they involved in a community?
Are they going to the beach and parties and traveling and stuff like that?
Those are the photos that I would highlight.
If you have kids, show your kids.
Show what you like to do with your kids.
I think that's an important part as well
to give kind of a full picture of the person that you are.
Now, I would say almost the exact same thing for the women as well in your profile.
Show things that you like to do.
Show places that you like to go.
Now, if you've only gone to Hawaii once, you don't need to spam 500 Hawaii pictures,
but, you know, mix it up.
Show the guys that might be looking at your profile, the type of person that you are.
Also show your friends.
Also show if you have kids.
That's important part of it as well.
And especially don't think about, hey, I just want to get the first date.
Think about how is this going to first date going to turn into 10 dates or to maybe
happily ever after?
And I think if you're not being honest with your profiles and your pictures, if you're,
if you're using too many filters or, you know, hiding your, you know, your hairline or
hiding your eyes or whatever that is, it might work once, but it's not going to work a second
time.
And lastly, I want to talk about this new thing that I've seen on dating apps, which are the
voice memos or the voice notes.
I think it's great.
I think every kind of like turning a person from 1D into 3D as much as you can is great.
I think there should be video notes.
I think as much of that out there as possible, I think is a great thing.
So there's less suspense when you're going to go meet the person.
There's more kind of expectations are going to be realized once you see them or meet them.
You know, and that's why I think it's also a great thing to talk to somebody on the phone, text with them before you ever meet them.
So you can kind of get a familiarity.
you kind of get a rhythm and a pace to the way you communicate
before you just have that awkward first hug
when you meet each other at the restaurant of the bar, wherever it is.
So I'm all a fan of as many different ways
to break the ice with someone before you actually meet them.
Getting ready for a game means being ready for anything.
Like packing a spare stick.
I like to be prepared.
That's why I remember 988, Canada's Suicide Crisis Helpline.
It's good to know just in case.
Anyone can call or text for free confidential support from a train responder anytime.
9-88 suicide crisis helpline is funded by the government in Canada.
I'm Nancy Glass, host of the Burden of Guilt Season 2 podcast.
This is a story about a horrendous lie that destroyed two families.
Late one night, Bobby Gumpbright became the victim of a random crime.
He pulls the gun.
Tells me to lie down on the ground.
He identified Termaine Hudson as the perpetrator.
Germain was sentenced to 99 years.
I'm like, Lord, this can't be real.
I thought it was a mistaken identity.
The best lie is partial truth.
For 22 years, only two people knew the truth,
until a confession changed everything.
I was a monster.
Listen to Burden of Guilt Season 2,
on the I Heart Radio app, Apple Podcasts, or wherever you get your podcasts.
Let's go!
Our IHeart Radio Music Awards are coming back.
Thursday, March 26th, live on Fox.
Watch as we honor the biggest stars from all genres of music
that you loved listening to all year long on your favorite IHeart Radio station
and the IHart Radio app.
Hosted by Ludacris.
Icon Award recipient John Mellencamp.
Innovator Award recipient.
Myly Cyrus.
With performances by Alex Warren.
Karen, Kalani, Lainey Wilson, Ludacris, Ray, TLC, Salt and Pepper, and Invoke.
Taylor Swift makes her first award show appearance this year.
Nicole Scherzinger, Nikki Glazer, Somber, Weiser, and more.
Watch live on Fox, Thursday, March 26th, at 87 Central.
And listen on IHeart Radio Stations Across America and the free IHard app.
Hey there, this is Josh from Stuff You Should Know, with a message that could change your life.
The Stuff You Should Know Think Spring Podcast playlist is available now.
Whether spring has sprung in your neck of the woods yet or not,
the stuff you should know, think spring playlist will make you want to get your overalls on,
get outside, and get your hands in the dirt.
You can get the Stuff You should know Think Spring playlist on the IHeart Radio app,
Apple Podcasts, or wherever you get your podcasts.
All right, we have one more email here from Layla, and she writes,
I'm trying to date with more intention the older I get.
How soon into dating a guy do I mention my timeline when it comes to getting engaged and married?
I feel like I wasn't up front quickly enough in past relationships, and I don't have time to wait anymore.
All right, Layla, great question, especially, you know, as we're working in Chapter 2, we're working in this next part of our lives.
Yeah, you do want to date with more intention, but I'd be careful about timelines.
timelines are just boxes and your box and somebody else's box might not be identical.
They might be similar, but as soon as you start putting a box into something and a deadline,
the other person might start to feel trapped by it.
Now, you want to make sure that you are continuing to make progress,
and I think that that's more of a personal responsibility thing,
where you're saying, okay, by the fifth date, I want to make sure I've met his family.
By the 10th date, I want to meet his kids, or whatever those little kind of,
hurdles are that you want to hit, make sure you're doing those. But maybe use those with the other
person as opposed to getting engaged and getting married. I think that stuff will come more
kind of organically as you're hitting these milestones. And it can be up to you to set those
milestones for that other person. So they know, okay, yeah. So meeting my family is important. Okay,
great. Meeting my friends is great. Okay. So put those things out there. Don't put a timeline on
engagement necessarily or a marriage necessarily. You can talk about that's your goal in life.
I do want to get remarried. I do want to, you know, have all these things and talk about those
things. But as soon as you say that I want that on June 15th this year, you might find a little bit
of apprehension from the other side. Maybe you won't, which is great. But I would tend to think
that the other person might have a similar timeline, but maybe not the exact same one. It would be
a shame to break up a relationship because you're off by a couple of months.
So I think that timelines definitely are more important to women than the art of men.
And again, a lot of it depends on how long has the person come out of a relationship.
You know, where is their headspace at right now?
And maybe that they, you know, both people want to get remarried.
And maybe they want to get remarried to each other.
One person's timeline says, I've been out of a relationship for five years.
I want to get married now.
The other person might say, listen, this is the third person I've dated.
I just need a little bit of time.
You know, before I'm actually ready.
So I think that, you know, it depends, you know, in, you know, timelines, I think for chapter one when you're first getting married.
I think that there's, you know, women definitely have very hard and fast timelines for it because they want to have babies and they want to start a family and all these other things.
In this next chapter, even though you might not think it, we have time.
You know, there is time to make sure that you are comfortable, that you're in the right headspace, that your finances are right, that your situations are right, that your kids are right.
right? There's all these mitigating factors in there where it might not just be the guy or the
girl that says, you know, I need some time, not because I haven't made up my decision about the other
person, but because I need to get my landscape right. I need to get my life kind of organized
so I can be the best partner I can be for the other person. So I think ultimately that, you know,
two compatible people are working towards the same thing. And hopefully you've talked about it.
Hopefully you've talked about your goals of if it is marriage, getting married. If it is moving
in together, it is moving in together. But I would just be careful about setting too many expectations
on exact dates. And like I said before, put in these little pieces, little little kind of hurdles that
you want to see happen along the way that are ultimately going to lead there. Meeting friends,
meeting family, meeting kids, vacation together. And, you know, and then the other things just
kind of come organically. And make sure that you're being responsible for yourself and protecting
your heart to make sure that you know the other person is working towards the same thing that you are.
But again, I'm just, I would be cautious about putting a firm deadline saying that we need to be engaged
by the end of the year. Because maybe that's not quite what the other person's thinking.
And again, it would be a shame to mess up something really great, you know, over a calendar.
All right, it looks like we have one last voicemail on this topic today. So let's hear it.
Hi, my name is Stephanie, and my question is, is it ever appropriate to have sex in a public setting when you are, let's say, above the age of 30? Or is it just entirely gross? Maybe like outside or in a restaurant, bathroom, etc.? Thanks. Bye.
Stephanie, that's a dozy to end up with. I love it. Is it gross to have sex in a public place
after you're 30? Well, usually the options for public spaces are pretty gross to begin with.
I mean, we're talking about bathrooms. You know, it might be hot and heavy and romantic in the
moment, maybe, but I'd still put that on the gross factor, especially, you know, if you're a mature adult,
I don't know what the 30 threshold is, but like, you know, if you've got, you know, kids, friends, anyone that could possibly ever find out about it, I think I'd be mortified. I like the idea. I mean, it's, you know, it's definitely a sexy thought. But I think that, I think probably sex in a park after 30, I just, I just can't imagine that that's anything that anyone would want to see. But if I'm thinking about it, okay, what are public places?
I'm just thinking, you know, in the bleachers of a ballgame,
which I think is probably a little bit more of an extreme thought,
but maybe if you're thinking about Mile High Club,
you know, if you have the flexibility and if you're back and hold up,
then that's an option.
And that's obviously something that people like to brag about
that they've accomplished.
You know, camping, I guess, is that a public spot?
I'm not really sure if it is or not.
But if it is, I think that's fine as long as, you know,
you haven't been camping for too long.
So I think that it probably depends on the place, the time, the situation.
And, you know, that's a, that there's a lot of factors, a lot of mitigating factors in there.
But generally, I think that, you know, sex in a bathroom and a bar probably leave that to the kids.
Well, I got to say that for our first time out, that was amazing.
I was not expecting the wide variety and colorful questions.
and thoughts, but I hope it was helpful, my Mr. Wright perspective on all these things.
And, you know, if you're single and in your chapter two and need some advice,
call us, email us, find all the info in the show notes, and make sure you follow us on socials.
And if you like this podcast, rate it, review it.
It's great to get some response on this.
This is I Do Part 2, an IHeart Radio podcast where falling in love is the main objective.
It's so interesting, host of the Spirit Daughter podcast where we talk about astrology,
natal charts, and how to step into your most vibrant life.
And today I'm talking with my dear friend, Krista Williams.
It can change you in the best way possible.
Dance with the change.
Dance with the breakdowns.
The embodiment of Pisces intuition with Capricorn power moves.
So I'm like delusionally proud of my chart.
Listen to the Spirit Daughter podcast starting on February 24th on the IHeart Radio
app, Apple Podcasts, or wherever you listen to your podcast.
I'm Nancy Glass, host of the Burden of Guilt Season 2 podcast.
This is a story about a horrendous lie that destroyed two families.
Late one night, Bobby Gumpright became the victim of a random crime.
The perpetrator was sentenced to 99 years until a confession changed everything.
I was a monster.
Listen to Burden of Guilt Season 2 on the
I Heart Radio app, Apple Podcasts, or wherever you get your podcasts.
Hey there, this is Josh from Stuff You Should Know with a message that could change your life.
The Stuff You Should Know Think Spring podcast playlist is available now.
Whether Spring has sprung in your neck of the woods yet or not,
the stuff you should know, think spring playlist will make you want to get your overalls on,
get outside, and get your hands in the dirt.
You can get the Stuff You should know Think Spring playlist on the IHeart Radio app,
Apple Podcasts, or wherever you get your podcasts.
Let's go!
Our IHeart Radio Music Awards are coming back.
Thursday, March 26th, live on Fox.
Watch as we honor the biggest stars from all genres of music
that you loved listening to all year long
on your favorite IHeart Radio station and the IHart Radio app.
Hosted by Lutocris.
Icon Award recipient, John Mellencamp,
Innovator Award recipient,
Miley Cyrus, with performances by Alex Warren,
Kalani, Laini Wilson,
Ludicrous
Ray
TLC
Sault and Pepper
and in vogue
Plus Taylor Swift
makes her
first award show
appearance this year
Nicole Scherzinger
Nikki Glazer
Somber
Weiser and more
Watch live on Fox
Thursday March 26th
at 87 Central
and listen on
IHeart radio stations
across America
and the free
IHeart app
This is an IHeart
podcast
Guaranteed Human
Thank you.
