Bad Dates with Jameela Jamil - Speed Dates: The Power Of Twinkly Lights (w/ Megan Gailey)

Episode Date: April 17, 2025

On this Speed Dates bonus episode, host Joel Kim Booster welcomes his good friend, comedian and podcaster Megan Gailey, to talk about planning a wedding, the good kind of bad boy, and the small thing that’s making her believe in love this week. Subscribe to our YouTube Channel for video clips.Merch available at SiriusXMStore.com/BadDates. Joel Kim Booster: Psychosexual, Fire Island, Loot Season 2Megan Gailey: @bettermegangailey on Insta, Los Angeles area: don’t miss the taping of Megan’s new stand-up special, May 10th and 11th 2025. RSVP is required, check Megan’s Insta for links and details! Subscribe to SiriusXM Podcasts+ to listen to new episodes of Bad Dates ad-free. Start a free trial now on Apple Podcasts or by visiting siriusxm.com/podcastsplus.

Bad Dates! Speed Dates! Hello, hello, hello and welcome to another Bad Dates mini episode, Speed Date. This is where we slow things down a little bit. No, no three guests shouting over top each other. No, no, no, no, no. This is just me one on one with a dear close personal friend of mine. And we're going to talk a little bit about their POV on love. Doesn't that sound exciting? And you should be excited because this guest joining me today is actually a friend of over a decade, somebody who is the first people, one of the

first people to ever be nice to me in the comedy scene in Chicago. I will never forget. She is a comedian, actress, and podcaster who has worked on Paws with Sam Jay and The Roast of Tom Brady. She co-hosts the podcast Sports Bitches. She also wrote a good portion of the Critics' Choice Award monologue with Chelsea Handler, which is not on the sheet today, but I know it,

and I know she's so excellent at it. It is Megan Gailey. Welcome, Megan. Thank you, and I know it and I know she's so excellent at it. It is Megan Gailey. Welcome, Megan. Megan Gailey Thank you. And I am joining you hot on the tails of receiving your save the date. Jared Sautner Oh, isn't I, it was such a harrowing process to decide it was like the hunger games of figuring out like, okay, I have to invite this person, but I would rather this gay person be there instead.

And it was like, what, and like all of like, the history of the comedy community that I would love to have there. You are actually, I think, one of the few comics that will be there. So you made the cut. Unfortunately, children didn't. No, no, no, no.

Someone actually texted, a dear friend texted me last week and was like, can I vent about something? I just got a wedding invite and it's no kids. And I think that's crazy. And I go, I you're misremembering my wedding. There were no kids. So like, your son, your kid wasn't there. I don't know.

I don't know if you hallucinated your child was there. But I, and she was like, Oh really? But like your niece and nephews were there. I'm like through dinner cause they were in the wedding. And then I sent them skedaddling. Yeah. Yeah. We're, and we are by the way, like outs, like sourcing childcare and covering it for people.

Oh my gosh. So it's like, there is no room for complaint. And it's like, I'm not even bringing my kid. I want to, I'm probably going to take my shirt off at my gosh. So it's like, there is no room for complaint. And it's like, I'm not even bringing my kid. I'm probably going to take my shirt off at my reception. I don't need children to see my nipples. You know, I famously did Molly at my own wedding. I know. So it's not for children.

No, weddings are for adults and adults only, unless you're Christian, I guess. Yeah. But, do you have any advice for me going into my wedding as I'm like about 270 days away right now? What is your best advice for me as a married lady who planned their own beautiful wedding with their own beautiful husband?

You know, I had expectations that everyone was going to bring their best self to my wedding experience. And I would throw that out the window. Everyone is actually gonna bring their worst self. Everyone, you're gonna go, oh my God, I've known you my whole life and this is the worst I've ever seen you behave. And like, I really, I had like a lot of different dynamics

happening on my wedding day, as you will too. Like that's just what it is. And I did not enjoy all the moments as much as I wish I had. The Molly helps, you know, then I was really in the group. But like, I wish there's definitely like, when I saw the video, there's like, I'm like smiling for pictures. And then when the photographer is done,

I like immediately I'm like, you know, it's like so sad. And so I would just say like as hard as it is and as many crazy people and strange, bizarro things that'll come at you, just tunnel vision on like, I want to have a lovely, beautiful time today. No, yeah, I told my planner, I was like,

I've never personally planned a party and enjoyed it while I was there because I'm so type A and so such a control freak. And I was like, I would like to not be in that headspace on my way. So like, you already have a planner and yeah, so you're you're way ahead of the game. So that's amazing. I guess now I'll start with the question that I always start with all of our guests with. And this is a pop culture related question, but it is, can you think of a moment or a couple from pop culture or a song even, um, that really sort of altered the way and sort

of set your POV on what love is? Like this can be something you watched as a child. It can be something you heard as an adult. Um, anything really that kind of like shaped the way you approached love or viewed love. Oh, you know, to come to mind, both from movies, one is like for some reason when they're dancing outside under the twinkly lights in She's All That. I really am just like, whenever I see a twinkly light now, it could be over a garbage truck.

I'm like, that's romantic. No, it's true. It's really true how that movie really indoctrinated us to the power of twinkly lights. Like, I see twinkly lights in a lesbian wedding in a Capital One commercial, and I'm crying. Stunning. And I'm crying.

Yeah. It's fair inunning. And I'm crying. Yeah. It's fair in love. Yeah. And then also right around that same time period when Heath Ledger sings during soccer practice of 10 Things I Hate About You, and it's like so embarrassing, but it's also such a gesture of like, I'm a bad boy, but in this like fun way, it really kind of exemplifies exactly who I married.

Has CJ ever done a big sweeping romantic gesture like that for you? No, but like he did tape toilet paper to his own shoe at his own high school graduation. And that's the type of bad boy that I like. Who would you say is the Freddie Prince and who would you say is the Rachael Lee Cook in your relationship?

I'm the Freddie Prince. No, I totally see that. I totally see that. I found him at Columbia College majoring in stand-up comedy and was like, get out of here, get those glasses off. And he took his glasses off

and I said, he's Filipino. You couldn't tell with the glasses. With the glasses, he looks straight up Chinese. And I love that so much. This is my thing. For people who don't know your backstory with CJ is that you were friends for many, many, many years before you even considered him

as a viable romantic partner. Is that correct? That is correct. And there was a real turning point for me and it was the 2016 election where I said, listen, I've done as much as I can. I voted correctly, I donated money. What I can do is stop having sex with white men.

And I never looked back. Not gonna be one inside of me for the rest of my life. CJ was the next penis I picked up, and I haven't put it down. white man. Like what changed? Like what changed in terms of how you saw him? Like when did you suddenly see him as like a viable sexual partner? Because it wasn't love first. It was a hookup first, correct? If I'm wrong? It was a hookup and it was, I'm going to say some success and a little glow up on both of our parts. Yeah, for sure. some success and a little glow up on both of our parts. Like, we both lost a little weight,

got a little better skincare, better clothes, and he had a really cool job and a really nice apartment, and he started dressing a lot better. And I was like, huh. No, and CJ does have an, he has rids, he does, but in a sort of of like in a way We're like it's not like he thinks she's too cool for you or anything like that Like it's very it's a very grounded sort of charisma that like is very natural and like appealing but also he's taping

Toilet paper to his shoe at his graduation. Yes, Like he hasn't always been tapped into it. And that's the trick. That's the trick. Yes. And that's what I would really suggest for any gals. Cause sometimes like a guy will get like quote unquote hot and then becomes like a jerk because he's like, I'm going to collect as much as I can.

And sometimes they're like, wait, I got hot? I didn't even know. Yeah. Sweet days. Sweet days. Sweet days. Sweet days. Sweet days. Sweet days. Sweet days. Sweet days. Sweet days. What a beautiful, inspiring love story

that you just walked us through the lens of two amazing early aughts romantic comedies that we do not get. The children are not getting high school romantic comedies in the way that we did. And it's sad, it's sad. And sometimes I'm like, should I make one or is that like weird that I'm pushing 40

and I'm like, let's have teens fall in love. Well, I mean, I don't even wanna look up what old white guy wrote both of those films. I know. That's a good point. That's like it's it's been happening for a time in Memorial. Like it is not it's not like they discovered a high school student who wrote a screenplay on spec. No. Like, well, you know who wrote Ten Things I Hate About You?

Oh, yeah. Shakespeare. Yeah. Yeah. And like he outdid himself. He sure did. Finally, moving on to our last question, and this is a very open-ended question. It can really be literal, metaphorical, however you wanna answer it.

What is making you believe in love this week, if anything? Oh, my son. And CJ, I was gone for four days and CJ held down the fort while we were in the throes of potty training and I have a two going on three-year-old. I mean, it's just not, even though he's a delight, it's just like a tough person to be one-on-one with

for four days. Yeah, no, I mean, they call it the terrible twos for a reason. Yeah, and he's actually pretty good, but like coming home yesterday, I went to pick him up at daycare, and when he saw me, I was like, a man loves me.

You know, like he threw down whatever he was playing with, and was like, mama! And I was like, come on! And we ran to each other, and I said, I! And I was like, come on! And we ran to each other. And I said, I missed you so much. He said, I missed you so much too. And it really made me forget that we descend every day

deeper into the depths of hell. Yeah, oh, and ain't, that is a tough, I can't even imagine, I mean, like, we're like lightly planning on having kids eventually. Luckily, we're not up against any sort of clocks here other than being old gay guys who are raising children. But that's the dream. I mean, yeah, no, honestly.

But it is like, it's sort of like, what are we doing? It's like, why in the world, looking around, would we want to introduce a new life or two into this world? And I don't say that to be shady to you who's currently in the throes of doing it. But yeah, six months or so. Yeah, like I have a new one coming

and I go on stage after comics all the time that are like, why would anyone have kids? You know, they do 10 minutes on not having kids and then I'm like, hello, bringing another one into the world. But mine are cute and hopefully helpful. Yeah, no, I think they will. And like they're the future. You know, everybody's going to be a little Asian in 20 years.

You know, every kid in L.A. is half Asian. It's crazy. Like I like my dad comes out here and he's like, what is happening? I'm like, they're all half Asian, dad, duh. My cousin and I, my Irish Catholic cousin and I, between the two of us, we've made four Asian men. I love it, I love it. And yes, they are, because in this climate,

one drop, baby, one drop. And that's enough. Yeah. I have to tell you a compliment before we wrap up. Okay. So I was having tea at the peninsula in Chicago with five of my closest girlfriends. And we were talking about Kathy Hilton's Christmas party,

which you lovingly took me along to. And my friend goes, oh my gosh, this girl that I was working with was like, how did she get to go to Kathy Hilton's Christmas party? And my friend goes, oh, well she went this girl that I was working with was like, how did she get to go to Kathy Hilton's Christmas party? And my friend goes, oh, well, she went with her really good friend, Joel Kim Booster, and her coworker goes, he's a gay icon. And you know it's true because a straight woman said it. Said it at work.

And then it was repeated to me at tea at the peninsula. And I go, I think Joel I think I need to hear this. Yeah, no, it is. It is nice to hear that. I have put in a lot of work to lead with my sexuality and every time I do. So, yeah, professionally gay now for quite a long time. Pride is a nightmare. I, you know, like it is

no fun anymore. So glad they're canceling it because of D.E.I is a nightmare. I, you know, like it is no fun anymore. So glad they're canceling it because of DEI initiatives now. It's such a relief, but and such a relief to be talking to such a good friend on the pod. I have loved this conversation so much, Megan. Where can people find you if they're looking to catch you on stage, which I highly recommend. You're still one of the best in the biz. Thank you. If I do say so to myself. My Instagram is at BetterMeganGaley.

I'm gonna be filming a special in Los Angeles over Mother's Day weekend. I will be eight months pregnant. Wow. And I'm so looking forward to that. All the details will be on my Instagram. And then even if you're not a sports fan And then even if you're not a sports fan, even better if you're not a sports fan,

my podcast that I host with two other female friends called Sports Bitches is just like a really fun romp into all the gossip and all of the hatred we feel for so many different things happening in the sports world. Yeah, no, I've picked in when like you guys are covering NBA stuff and it's a lot of fun. And I'm not even like super about it. You know, well, they're the best dressed and like, like the most fun drama to me. Yeah, and they are the richest and they are,

they are black men creating generational wealth. And that also gives me hope right now. You know, I go. It's like they are giving a platform for the world to be able to do what they want. And I think that's the biggest thing. And I think that's the biggest thing. And that also gives me hope right now. You know, I go. It's like they are giving a platform for a woman

to eventually become a real housewife. Yes, exactly. You know, and that is important. We need to be churning out these ladies, you know. The Dallas Mavericks were also at the peninsula and there's a chance Anthony Davis heard you called a gay icon. So I hope that affected his life in many different ways.

Megan, I can't wait. I can't wait to I think I'm here during your special and I would love to come and see it as I recommend everyone else in the LA area do. Even even if you're in the OC, come, you know? Please, escape! Yeah, get out of there. In any case, you can hear another episode of Speed Date, the Bad Dates mini episode every Thursday.

We also are coming out with a new episode of Bad Dates on Monday, so check us out on the main feed. If you like what you're hearing now, rate and review five stars, please. And in any case, now I'm leaving you. That's it, that's it. This has already gone longer than a mini episode should have.

And I hope you feel grateful for that because it'll never happen again. Goodbye. Bad Dates is a production of Smartless Media created by Robert Cohen, executive producers are Richard Corson and Bernie Kaminsky. We will be back for more Bad Dates. Smart. Plus.

Media. Smart. Plus. Media. Bless me I