Dear Chelsea — “Dating the Good Dad with Judy Greer”
Podcast: Dear Chelsea
Host: Chelsea Handler
Guest: Judy Greer
Date: October 2, 2025
Episode Theme: Navigating love, family, step-parenting, sobriety, and core values, highlighted through candid advice and comic honesty.
Episode Overview
Comedian and author Chelsea Handler welcomes actress Judy Greer for a wide-ranging, humorous, and heartfelt episode. They dive deep into the challenges of step-parenting, midlife, career pivots, marriage, and sobriety, responding to listener stories along the way. With Judy’s signature warmth and Chelsea’s irreverence, the pair offer both practical and emotionally honest advice, making for an engaging, relatable listen.
Table of Contents
- Opening Banter & Health Talk
- Judy Greer’s Career Reflections
- Stepmotherhood & Dating “the Good Dad”
- Sobriety, Age, and Changing Generations
- Listener Questions & Advice
- Judy on Family, Only Children, and Marriage Decisions
- Notable Quotes & Memorable Moments
- Timestamps for Key Sections
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1. Opening Banter & Health Talk
- Chelsea Handler describes her peaceful Canadian getaway, the all-female vibe, and her love of gloomy weather (03:51-04:10).
- She candidly shares her current struggles with menopause, hormone replacement therapies, and her vitamin and supplement regimen (04:27-06:20).
- Mental acuity, gratitude journaling, and lifestyle advice are delivered with comedic self-awareness.
- Chelsea: “I have no estrogen and I have no testosterone. So there is a reason that... my words are not making any sense these days.” (04:27)
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2. Judy Greer’s Career Reflections
- Chelsea gives a lightning-fast rundown of Judy’s extensive film and TV credits, with banter about aging and prescription sunglasses (09:01-10:12).
- Discussion of "character acting" and longevity in Hollywood.
- Judy: "I don't know [if I am a character actor]. Aren't we all character actors? ...I think that's a funny description. It just means that you're not the star, that's all." (10:30-10:41)
- They reflect on what it means to “make it” in the entertainment business, surviving and thriving as women in midlife (11:11).
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3. Stepmotherhood & Dating “the Good Dad”
- Judy delves into being a stepmom, navigating boundaries and familial roles (21:23-24:29).
- Judy: “You have all the responsibility and none of the authority. ...Now my kids are old, but when they were young, you are like a babysitter extra sometimes.” (21:33)
- Her experience dating a “good dad” altered her own trajectory—she discovered fulfillment in being a stepmom, influencing her own stance on having biological children.
- Judy: “It influenced my decision not to have one of my own.” (24:29)
- They both analyze societal pressure and the real motivations behind having children.
- Judy: “Women who want their babies get their babies, man.” (25:13)
- Chelsea: “...we always have [the thought] in the back of our minds because of like, society...” (25:23)
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4. Sobriety, Age, and Changing Generations
- Discussion about post-pandemic drinking habits: Judy is now sober, noting many have tried but returned to drinking (19:20-20:11).
- The pair comment on generational culture shifts—Gen Z and young people drinking less, and the impacts on social life and the restaurant industry.
- Chelsea: “Gen Z is, like, not drinking at all... our generation, we're heavy drinkers, and then everyone is getting sober...” (20:55)
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5. Listener Questions & Advice Segment
<a name="q1"></a>Q1: Accidentally Dating a Trump Supporter (41:53-47:56)
- Question from Erica, a Canadian feminist in LA’s music industry, who discovers her promising new boyfriend voted for Trump “for economic reasons.”
- Judy and Chelsea discuss the realities of value conflicts, especially regarding family planning and long-term partnerships.
- Chelsea: “I would hate to say you can’t date somebody that voted for Donald Trump, because I just feel like that is just so narrow minded. But right now... it’s just so ugly...” (43:36)
- Judy: “If that’s what someone’s really looking for... how are you going to raise your kids together?... That would worry me.” (44:09)
- Both agree: Fundamental value differences—especially on key issues—are likely a deal-breaker for serious relationships.
<a name="q2"></a>Q2: Supporting a Partner through Job Loss (48:13-66:41)
- Caller Charlotte describes financial stress as her wife, historically the breadwinner, remains unemployed for a year following her fourth job loss. Charlotte is conflicted, frustrated, and unsure whether to stay or go.
- Chelsea and Judy question the dynamics — is this circumstantial, or a repeated pattern? Judy notes four layoffs in eight years is concerning.
- Chelsea: “She’s not lying around. She’s not a drug addict. She’s not a drunk... You have to figure out a different approach...” (54:46)
- Judy: “You can’t control other people... If you want more money... you have to shift the focus onto yourself.” (56:50 & 57:36)
- Both emphasize support, communication, exploring therapy, and changing mindsets—rather than abandoning the relationship, especially when kids are involved.
- Chelsea: “Sometimes you’re going to be pulling the cart. Sometimes she’s going to be pulling the cart. You guys are doing this together.” (57:32)
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6. Judy on Family, Only Children, and Marriage Decisions
- Judy shares stories about being an only child, her mother’s resilience (including surviving a gunshot), family similarities, and Ohio roots (25:42-29:22).
- Discussion about differences in family dynamics, conflict resolution, and people-pleasing tendencies.
- Judy: “I’m terrible at fighting. ...I think that’s wrong, and I think it shouldn’t be that way. But that, I think, is something maybe that is an only child thing.” (29:36)
- On marriage: Judy didn’t believe in “love at first sight,” but recounts the trajectory of meeting her husband—a “good dad”—and learning to appreciate chemistry without pressure to prescribe meaning or destiny (30:24-34:11).
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7. Notable Quotes & Memorable Moments
- "You have all the responsibility and none of the authority." — Judy Greer on step-parenthood (21:33)
- "Women who want their babies get their babies, man." — Judy Greer (25:13)
- "Sometimes you’re going to be pulling the cart. Sometimes she’s going to be pulling the cart. You guys are doing this together." — Chelsea Handler (57:32)
- "I'm terrible at fighting...a fight means a fight, and it needs to be dealt with and talked about, and you have to go to therapy about it." — Judy Greer (29:39)
- "The best way to change people is by changing yourself." — Chelsea Handler (61:43)
- Judy recounts how Emma Thompson models kindness, boundaries, and not being “afraid of being disliked”—a role model for women who people-please (73:55-74:37).
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8. Timestamps for Key Segments
- Wellness, hormones, supplements: 04:27-06:32
- Judy Greer joins / aging & career: 09:01-13:13
- "The Long Walk" & new movie chat: 13:17-14:52
- Stepmotherhood and marriage: 21:23-25:13
- Sober living & Gen Z shifts: 19:20-20:55
- Only child & family dynamics: 25:42-29:36
- Dating and chemistry: 30:24-34:11
- Listener Q1: Dating a Trump voter: 41:53-47:56
- Listener Q2: Breadwinner wife unemployed: 48:13-66:41
- Closing reflections & Emma Thompson: 73:55-74:38
Takeaways
- Judy and Chelsea bring sincere warmth, vulnerability, and humor to tough family questions.
- Step-parenting, sobriety, and reconciling life’s expectations are recurring themes.
- The advice segment is both practical and compassionate, never black-or-white.
- Memorable lesson: In relationships, when in doubt, focus on changing yourself and on clear communication—there are rarely simple answers, but there are always steps forward.