Why Won't You Date Me? with Nicole Byer

Episode: Dating as a Child Star, Proposing Naked (w/ Josh Peck)

Release Date: January 31, 2025
Host: Nicole Byer
Guest: Josh Peck

Episode Overview

This episode features actor, comedian, and podcaster Josh Peck joining Nicole for a lively, freewheeling conversation. The two dive into what it was like navigating relationships as a child star, discuss body image, share memorable relationship and proposal stories, and reflect on growth, mental health, and advice for singles. True to the show’s spirit, the exchange is hilarious, candid, and at times surprisingly heartfelt—with both Nicole and Josh trading stories about love, drugs, childhood, and the joys and absurdities of being human.

Key Discussion Points & Insights

Movies, Pop Culture, and Childhood Influences

• Nicole and Josh riff on films they've (and haven't) seen, establishing a quick rapport based on shared and divergent movie memories.
  • Nicole hasn't seen Good Will Hunting, No Country for Old Men, or There Will Be Blood ([04:18–04:40]).
  • Josh reminisces about growing up with TV and classic comedies as his "friends," influencing his drive to perform ([33:22–33:33]).
• Playful banter about action films (John Wick, The Beekeeper) segues into a discussion of secret societies and movie tropes ([05:07–07:32]).

Quote:
“I want to be in some sort of action movie as like the D bop bop bop mechanical...the comedic relief, just insane. And everyone else gets to do the action and maybe they let me do it like one time.”
—Nicole Byer ([07:10])

Relationship Stories: Meeting & Proposing

How Josh Met His Wife

• Met at a Halloween party; Josh was a “waiter,” his (now) wife was Olivia Newton-John from Grease ([08:54–09:04]).
• Friend "Ani" played matchmaker, orchestrating the first conversation ([10:00–10:30]).
• First date happened after Josh returned from filming a dance movie in Paris—Battle of the Year with Chris Brown ([11:38–12:17]).
• Longevity Advice:
  • "Don’t leave. Stay. Stick around." ([12:28])
  • Value in fighting through difficulties together.

Quote:
“I don't know, we recognize the value in each other. Like, even when it got bad or like hard, I knew, like, no, this person's very, very special.”
—Josh Peck ([12:54])

The Naked Proposal

• Josh proposed to his wife naked, right before their trip to Paris ([18:45–22:53]).
• Wanted an unpretentious, intimate proposal—“I wasn’t the guy to do it in Europe” ([19:38–19:45]).

Life, Sobriety & Mental Health

• Nicole and Josh discuss ADHD, substance use, and how they manage or have managed each ([15:27–17:44]).
  • Nicole is candid about liking uppers for focus; Josh has been sober for 16 years ([16:24]).
• They joke about drug use within their relationship to ADHD and coping mechanisms ([16:10–17:44]).
• Josh discusses being “a gigantic teen” and growing up metabolically challenged ([23:15–23:37]), and shares his journey with weight, health, and self-acceptance.

Quote:
“I think I wasn't attracted to me. And that was the vibes I was putting out. Unfortunately.”
—Josh Peck ([25:51])

Body Image and Food Relationships

• Open exchange about body size, attractiveness, and the odd freedom that can come with being heavy ([25:46–29:32]).
• Food nostalgia: Nicole and Josh swap stories of childhood secret snacking and the hierarchy of vending machine snacks ([29:00–29:50]).
• They both discuss diabetes, medication (Manjaro), and the way food “noise” runs in the background of life and how medication can help ([40:20–43:00]).

Quote:
“After you hit a certain point, you just eat whatever you want. You’re already there...like, have a nice time.”
—Nicole Byer ([28:38])

Parenting, Childhood & Career

• Josh talks about moving from NYC to LA at 13 for showbiz, landing on The Amanda Show and then Drake and Josh ([32:57–33:17]).
• Shares about having two sons—“that’s enough souls to take care of” ([30:39])—and the wild joy of parenting.
• Nicole fondly recalls nannying boys and shares her delight in big, chunky babies ([30:56], [49:11–49:30]).

Dating, Apps, and Real-World Advice

• Josh started dating “properly” around 18 after losing weight, feeling he had to make up for lost time ([31:18–31:30]).
• Laments not being from the dating app era, instead recalling “meeting someone at yoga or the local Whole Foods” ([47:04–47:32]).
• Both champion starting conversations with strangers in real life.

Quote:
“You could write them the dumbest shit and they’ll be like, he’s so hilarious... and on the other side, if they’re not into it, you could be Shakespeare and they're not. It’s not gonna hit.”
—Josh Peck ([14:41–14:53])

• Nicole highlights the importance of intention, even if execution is a little wobbly:
  “I live by ‘intention is everything, execution might be lacking’” ([11:03]).

Final Advice for Singles

“Keep at it. The right person will find you. Double down on the things that you know are good.”
—Josh Peck ([46:59])

“Fall on your face. Be rejected. Put yourself out there. Fuck it up. Who cares?...Everyone listening’s going to be forgotten. Thus fall on your face. Be rejected.”
—Josh Peck ([48:15])

Notable Quotes & Memorable Moments

| Timestamp | Speaker | Quote/Context | |-----------|---------|---------------| | 07:10 | Nicole | “I want to be in some sort of action movie as...the comedic relief.” | | 12:28 | Josh | “Don’t leave. Stay. Stick around.” (on relationship longevity) | | 14:41 | Josh | “If this person is down for you, you could write them the dumbest shit and they’ll be like, he’s so hilarious.” (on dating anxiety) | | 18:45 | Nicole | “How did you propose to your wife?” / “Naked.” — Josh | | 23:19 | Josh | “I was huge. I was a gigantic teen.” | | 25:51 | Josh | “I think I wasn’t attracted to me. And that was the vibes I was putting out.” | | 28:38 | Nicole | “After you hit a certain point, you just eat whatever you want. You’re already there…” | | 42:47 | Nicole | (on food cravings returning if off medication): “Yes. Yes. Sure does. It sucks.” | | 46:59 | Josh | “[For singles:] Keep at it. The right person will find you. Double down on the things that you know are good.” |

Highlighted Segments with Timestamps

• Movie Talk & Pop Culture Banter: [02:22]–[07:32]
• How Josh Met & Proposed to His Wife: [08:54]–[22:53]
• ADHD, Sobriety & Drug Stories: [13:41]–[17:44]
• Body Image, Weight, Food Nostalgia: [23:01]–[29:50]
• Parenting & Career Origins: [30:36]–[33:17]
• Advice on Dating, Real-World Connections: [46:59]–[48:49]
• Lightning Round & Sign-Off: [46:52]–[52:23]

Tone & Style

The entire episode is marked by Nicole and Josh’s quick wit, playful self-deprecation, and open-heartedness. Laughter and candid realness punctuate the show, making room for both vulnerable revelations and absurd asides—typical of Nicole’s signature style. Both balance honesty about life’s challenges (body image, health, drugs, grief) with levity, encouragement, and warmth.

For listeners curious about dating as a child star, body confidence journeys, honest takes on love, or simply a fun, inclusive, and raucous conversation—this episode is a can’t-miss.