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Scared to Propose for a YEAR?? w/ David Cross | First Date with Lauren Compton

First Date with Lauren Compton

Tue Apr 28 2026

Summary

Podcast Summary: "Scared to Propose for a YEAR?? w/ David Cross"

First Date with Lauren Compton (YMH Studios)
April 28, 2026

Episode Overview

In this lively episode of First Date with Lauren Compton, Lauren sits down with legendary comedian, actor, and writer David Cross. Together, they embark on a faux first date, exploring David’s uniquely winding road to marriage, his nerdy romantic misadventures, parenting challenges, and the joys and absurdities of long-term relationships. The conversation is candid, laugh-out-loud funny, and sprinkled with memorable anecdotes and philosophical musings on adulthood and family life.

Key Discussion Points & Insights

Life in New York, Family, and Daily Routine

David’s Move to New York:
- Moved in 2001, originally from Atlanta.
- Loves New York despite its cost:
  
  "I would not live there if I didn't love it because it's expensive, but I love it, love it, love it, love it." (00:57)
Dad Duties:
- Most of his day is spent on childcare and basic living, not just creating comedy.
- Daughter (9 years old) goes to public school nearby.

Secrets to a Long Marriage

14 Years Married:
- Married to actress Amber Tamblyn, going on 14 years:
  
  "It will be 14 years in October." (02:46)
Secret Sauce:
- Being with someone who understands the demands of the entertainment industry is crucial.
- Time apart for work can actually strengthen the relationship:
  
  "Spending time apart is good as well." (03:53)
- Humorously credits having a kid:
  
  "Kid helps... It hurts but it helps." (03:11)

The Serendipitous Love Story

Multiple Missed Connections:
- First met at an industry event while David was in a bad place post-breakup.
- David left Amber a note on a film set in NY via a PA—she never responded.
- Months later, they randomly met on a tiny plane to Shreveport. Amber glared at him until he recognized her.
Developing Chemistry:
- Became friends in Shreveport, hung out platonically for six weeks, hesitant due to her being a fan and younger.
- Eventually, the undeniable chemistry led to a first kiss:
  
  "I kissed her. And that was it. And she basically moved in after that... We've been together ever since." (14:35)
Amber as a Fan:
- She had a T-shirt with David’s face and loved Mr. Show and his standup.
- Lauren: "But she loved. She was, like, already in love with you." (14:34)
- David: "Yeah. I didn't know that... I thought she just admired me." (14:37)

The Notorious Year-Long Proposal Saga

David’s Procrastination:
- Custom designed and made a ring—and carried it around for a year, through multiple countries, never finding the “perfect” moment.
Failed Proposal Plans:
- Planned to propose atop the Santa Monica Ferris wheel but backed out:
  
  "If she said no, then I'm at the top of a Ferris wheel... That's why I pussied out." (17:18)
- Next plan: hot air balloon in England—canceled due to weather.
- Considered a safari proposal, but someone famous did it first and “ruined” the idea.
Actual Proposal:
- Finally, after returning home exhausted from another failed attempt, proposed spontaneously in their tiny London flat:
  
  "I just changed... I don't remember a whole lot... I just sort of threw the ring at her and asked her to marry me. And it's really bad, cause I don't remember. I was a mess... I was, like, so fucking nervous." (21:32)

Wedding Details

Epic Wedding Weekend:
- Three-day camp-style celebration at a rented Jewish kids’ camp in upstate New York.
- Activities included ziplining and cabins for guests.
- Food trucks, performances by Yo La Tengo, DJ set by Questlove:
  
  "It was awesome... Had Yola Tengo playing... Questlove DJ'd... Huge party out by the river. It was beautiful." (27:39)

Parenting: The Realest Talk

Lauren’s Journey:
- Delays her own wedding due to pregnancies and wanting to enjoy the party.
- Describes the difficulty of juggling wedding plans and breastfeeding.
Sleep Survival:
- David’s take: hiring a night nurse was life-changing—eventually:
  
  "I want at least two weeks of knowing... not getting any sleep... right before she was supposed to come, she got sick... I was fucking going nuts." (32:29)
Routines & Milestones:
- Both discuss nap routines, toddler eating habits, and sleep training wins.

Food, Tattoos, and Growing Up (Sort Of)

Food Adventures:
- Lauren’s husband owns Black’s Barbecue; both share their kids’ early love for brisket and BBQ.
Tattoos:
- David’s first tattoo: a pretzel, then covered up, then expanded into an elaborate "God spanking Hitler" cartoon, and a pig for BBQ.
- On maturing:
  
  "I didn't really grow up until I was in my mid-40s." (44:17)

Notable Quotes & Memorable Moments

On Life with Kids:

"If you don't [sleep], absolutely nothing works... the wheels fall off the bus." (34:49) — Lauren
On Proposing for a Year:

"And then I just sort of, as she describes it, just sort of threw the ring at her and asked her to marry me. And it's really bad. Cause I don’t remember. I was a mess... And I wasn't high or drunk or anything. I just. I was, like, so fucking nervous." (21:32) — David
On Parenting:

"Get that woman here. I don't care what the fuck she's got. I don't care if she's got aids. Get her here. I can't do this anymore." (33:58) — David (On desperately needing a night nurse)
On Wedding Parties:

"It needs to be a party… I want champagne. I want wine. I want to, like, enjoy it.” (29:31) — Lauren
On Time & Maturity:

"I didn't really grow up until I was in my mid-40s." (44:17) — David

Timestamps for Important Segments

00:57 — David on Loving (and Hating) NYC
03:11 — Secret to 14 Years of Marriage
07:42 — Serendipitous “Meet Cute” with Amber
13:29 — Realization of Chemistry
15:38 — The Year-Long Saga of the Proposal
21:32 — The Actual, Awkward Proposal
24:24 — David’s Shift on Marriage
27:39 — The Legendary Wedding Camp Weekend
30:29 — Lauren on Pregnancy/Wedding Timing
32:29 — The Hell of Sleep Deprivation
37:38 — The Kids’ Diet Chronicles
38:41 — Tattoos and Regret
44:17 — Delayed Adulthood

Final Thoughts

David Cross’ hilarious, brutally honest storytelling combined with Lauren's warm, playful style makes this episode both deeply relatable and thoroughly entertaining. Listeners are treated to tales of awkward romance, spectacular wedding parties, the hazards of parenting, and the unpredictable journey toward growing up—a little. Whether looking for relationship wisdom, parenting tips, or just a good laugh at the chaos of adulthood, this episode delivers.

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Transcript

Interviewer (0:00)

I'm so excited to see you tonight. First Date, baby. First date. I can't wait. First date. What is up, you guys? Thank you for watching another episode of First Date. My guest today is an actor, a writer, producer, comedian. You can see his new special, the Actor the End of the Beginning of the end on YouTube. Now give it up for David Cross. Oh, that's all the interaction we get with a live studio audience.

David Cross (0:37)

Great. I'll take it. I'll take it.

Interviewer (0:39)

How are you?

David Cross (0:39)

I'm good. How are you?

Interviewer (0:40)

I'm good. We were just talking. So you live in New York?

David Cross (0:43)

I do.

Interviewer (0:44)

Were you born there?

David Cross (0:45)

I was not. I was born in Atlanta, where I mostly grew up.

Interviewer (0:52)

When did you move to New York?

David Cross (0:55)

2001.

Interviewer (0:56)

Do you like it?

David Cross (0:57)

I love it. Yeah. I would not live there if I didn't love it because it's expensive, but I love it, love it, love it, love it.

Interviewer (1:05)

What do you do on like a day to day basis in New York?

David Cross (1:08)

Well, I mean, now it's mostly about my kid, but, you know, just chores and like right now I'm putting material together for a new set to go out on tour eventually. So a lot of that just entails walking around and trying to notice things.

Interviewer (1:39)

How old is your kid?

David Cross (1:40)

Nine.

Interviewer (1:41)

Oh, wow. So he's like an adult.

David Cross (1:44)

He is a she, Madam.

Interviewer (1:46)

She is an adult.

David Cross (1:47)

David Cross (4:23)

So initially, I know this is going to. All right. So initially, we met at. It was either. It was like the Golden Globes or a Fox thing or something like that. And I knew she was a fan. I know this sounds creepy as fuck, so I had been in this relationship with somebody and my being away, having to go to LA to work on Arrested Development was not good. And. And I understand we had a bad breakup and she broke up with me in a kind of shitty way. And. But I understand that this was not what she signed up for. We had been going out for like three and a half years, and then I was just gone all of a sudden for quite a bit. And. And then somebody on the show unarrested, knew my wife and said, oh, I've got the perfect person for you. And I was not interested. I wasn't in a place to date or anything at that point. It was still too fresh and I was processing all this stuff. And also, again, it was a shitty breakup. And she told me who it was and I was like, what? She's a child? And I had met her and I had this kind of awkward interaction too, because I was high, as I was so high, anytime I went to those Emmys or any of those things, I. I wasn't comfortable. And I, you know, tried to compensate by drinking and getting high and all kinds of stuff. And so all that is to say that I'd met her prior to. Years later, she was shooting a movie across the street from my apartment in New York, and I had. So I had an interaction with her prior to this. And then I was going to walk my dog. It was A puppy at the time. And I saw she was shooting, and I. It was at a pizza place, video place on the corner. And I tapped on the window when they were on a break, and she gave me the little heart symbol with her hands. And I was like, I'm walking my dog. You know, mouthing, I'm walking my dog, but I'll blow whatever. So I. I got. I left her a note to get I. That I gave to a PA to give to her saying, hey, I don't know how long you're in town for. I live right here on the corner. If. If you don't know New York, I'm happy to tell you where to go or take, you know, whatever. You know, that kind of thing. You know. Let me know if you're interested. Never heard from her again.

David Cross (19:28)

We can't send you up. It's too dangerous. And. And then we're like sitting out in the middle of nowhere. Cause we got a taxi there from a bus station, from a train. And then this. And I've got the ring on me. And then this couple, this very nice couple is like, we can give you a ride back to town to get a bus at least. I was like, all right, thank you. And then. So later that night, and I had to shoot the next morning. And it's a show that I wrote and acted in and produced. So it's early. My hours are, you know, 18 hours a day. And I was like, fuck this. I'm going to propose enough. It's been a year since I've been carrying this fucking thing. And I think I had. In South Africa, too. I think I was going anyway. So that was it. That was the thing. Somebody was on a safari. That was it. So I went on the safari. That's the other thing I was. It was like. I want to say it was Prince William or somebody, but somebody famous was. Was on a safari and proposed to his. Also famous Wife. And I'm like, motherfuck. It was like literally six days before. I'm like, God damn it. And so I said, all right, enough's enough. And I. You know, we're having a completely normal evening. We're in this tiny little flat that had, like, those round stare of things. And I just changed. This is where it's better if she tells the story, because I don't remember a whole lot. But you just blacked out kinda. I went up the stairs and I came back and I started talking to her, like, so, you know, you're really important to me. Whatever I said, I don't remember. You have to ask her, because she. She's like, what the fuck? And she thought. And she said this to me. She. Did you go upstairs and get high? She thought I was high. She thought I had done drugs. And not even, like. Not like an unspecific, unspecified drug, just a drug. You clearly drugged yourself because you're not acting normal. Your eyes are flying all over the place. What. You sound weird. Like, what's going on? And. And then I just sort of, as she describes it, just sort of threw the ring at her and asked her to marry, you know, if she'd marry me. And then. And it's really bad. Cause I don't remember. And I was a mess. And I wasn't high or drunk or anything. I just. I was, like, so fucking nervous.

Interviewer (25:07)

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