Dear Chelsea – "Becoming a Male Lion with Haley Lu Richardson"
Date: November 6, 2025
Host: Chelsea Handler (with Katherine Law)
Guest: Haley Lu Richardson
Episode Overview
In this lively and heartfelt episode, comedian and advice power-house Chelsea Handler welcomes actor and writer Haley Lu Richardson for a candid, witty, and deeply relatable conversation. The main theme of the episode centers around navigating growth, heartbreak, womanhood, independence, and self-discovery, all peppered with playful humor and self-reflection. Together with co-host Katherine Law, they offer sincere advice to listeners facing challenges in relationships and dating, while digging deep into what it means to become empowered – or, as Chelsea dubs it, "becoming a male lion."
Key Discussion Points & Insights
1. Chelsea’s Las Vegas Story: Gambling and Karma
[04:15 – 06:07]
- Chelsea shares her post-Vegas show antics, recounting how she gifted her gambling money to friends, lost it all, then borrowed $1,000 from a stranger to win it back.
- Reflects on being content with breaking even and the value of gratitude:
"That's what women can teach men. To not be so avaricious. To just be happy with what you have and be grateful." – Chelsea ([05:46])
- The conversation segues into the necessity of practicing gratitude even when it's hard.
2. Introducing Haley Lu Richardson
[06:13 – 07:12]
- Katherine and Chelsea gush about Haley, with affectionate ribbing about her choice to live in Arizona.
- Chelsea spotlights Haley's book "I'm Sad and Horny" and her knack for raising group spirits.
3. Managing Moods & Self-Care Rituals
[07:16 – 09:02]
- Chelsea and Haley discuss how to handle negative moods:
- Chelsea: "If I'm in that state, I just have to numb out because otherwise I become, like, hysterical."
- Haley shares that crafts like beading and crocheting serve as her own creative Xanax.
4. Reading from "I'm Sad and Horny"
[10:00 – 10:26]
- Chelsea reads Haley’s poem “New Place Alone in South Africa,” a meditation on breakups and being alone.
"To be alone in South Africa is better than being lonely with you." – read by Chelsea, written by Haley ([10:20])
5. On the Value of Being Alone & Transitioning into Womanhood
[11:02 – 12:31]
- Haley and Katherine discuss the fear of being alone, emphasizing it’s better than loneliness within a relationship.
- Chelsea and Haley muse on what it means to feel like a “woman,” a “lioness” – and then, in Chelsea's words, “actually, I feel like a male lion.”
"I didn't really feel like a woman until I turned 50 this year." – Chelsea ([12:03])
"I'm excited to feel like a male lion." – Haley ([12:14])
6. Organic Deodorant & Accepting Imperfections
[13:14 – 14:07]
- A comic detour on Haley’s sweaty armpits leads to talk about organic deodorant, with the group agreeing to “accept the world as it is.”
7. Processing Breakups: Reflection, Journaling, & Growth
[14:07 – 18:21]
- Haley details her experience moving beyond a pivotal 7-year relationship:
"All I saw in my life was just this person for the rest of it… I never even went to the place where I would be like, but what if it doesn't work?" ([14:28])
- Journaling as a healing tool: Haley’s ritual includes reading old journals and ritually destroying them for closure.
- Growth isn’t linear—insight emerges years later.
8. Handling Heartbreak: Taking Responsibility for Healing
[18:21 – 21:33]
- Chelsea reframes heartbreak, underscoring the importance of restoring one’s energy and not blaming exes.
- Haley introduces the idea of compassion for even the “shittiest people,” recognizing everyone’s doing their best in their circumstances.
9. The Drama Triangle & Codependence vs. Interdependence
[27:16 – 31:18]
- Haley introduces the “drama triangle” (bully, victim, rescuer) and the importance of getting off it for healthier relationships.
- Clear distinctions between codependence (needy, self-sacrificing) and interdependence (healthily relying on each other).
10. Books and Pop Culture: Fantasy, Crafting, and the Jonas Brothers
[21:37 – 36:54, 31:18 – 35:54]
- Book talk: Haley gushes about fantasy author Brandon Sanderson.
- Haley’s love for Disney World and the Jonas Brothers, recounting her experience dancing in their music video and her fangirl moments.
11. Writing, Poetry, and Taylor Swift
[36:54 – 41:09]
- Chelsea draws parallels between Haley’s poetic writing and Taylor Swift’s lyricism.
- Discussion on the impact of good parenting, noting both Haley and Taylor Swift’s stable upbringings as the foundation for their current resilience and creativity.
12. Parenting & Sacrifice
[42:24 – 43:21]
- Haley reflects on her parents’ rare dedication:
"The sacrifice my parents made to, like, let me leave high school at 16 and move to LA... they sacrificed and like made it possible for me, which I do think is rare." ([42:28])
Listener Advice Calls
1. Bri, 37: Navigating Breakup, Workplace Crush, & Letting Go
[46:46 – 57:17]
- Bri describes ending a long-term relationship, emotionally transitioning to a coworker (Bryce), but struggling as Bryce pulls away.
- Chelsea’s advice:
"You have to embrace your womanhood... You are so powerful. If you want this to happen with this guy at work, it can happen. But respect the fact that you just got out of something and going straight into something isn't really going to be the most valuable lesson." ([53:37])
- Haley commends Bri’s self-awareness and self-control, encouraging her to view her restraint as “impressive [and] honorable.”
- Both hosts advise letting guilt be a lesson, but not a burden.
2. Lauren, 33: Therapist Seeking Love in a New City
[58:28 – 65:38]
- Lauren, a therapist, is moving to Madison, WI, to improve her dating prospects. She asks for advice on meeting singles in a new city.
- Chelsea prescribes mingling through co-ed activities:
"Join all sorts of clubs you don't give a shit about... tennis, biking, kayaking. All of those are going to yield both sexes. So you're going to meet friends and you're going to [meet men]." ([59:44])
- Both Chelsea and Haley swear by boldness – complimenting strangers, taking risks, and putting oneself forward.
- Haley, also single, humorously shares her own DM-sliding stories and her resolve to "hold on to hope and not become bitter."
- Katherine relays a family anecdote about dating as a job, rotating through first-date outfits.
Notable Quotes & Memorable Moments
- Chelsea on heartbreak:
"You have to pick yourself back up... It's not about other people coming in to save you, it's about you saving yourself." ([18:38])
- Haley on growth:
"The journey of the heartbreak is so nonlinear... but it's nice to see... there's been a growth." ([17:15])
- Haley on parental support:
"My parents always believed in me... and made this life that I live possible. I do think it's rare." ([42:28])
- Chelsea on risk and regret:
"The only thing I think I regret in my life is not actually being as bold as people think I am with regard to meeting guys." ([61:26])
- Haley’s humor:
"I'm enjoying myself. And also so is your vibrator. I have multiple besties these days. Different shapes for different moods. Love them all equally." ([71:31])
- Chelsea’s rallying cry:
"Women are stronger than men. And that's not sexist, it's true." ([53:37])
Timestamps for Important Segments
- Vegas, Gratitude, and Being a Woman – [04:15–06:12]
- Introducing Haley and Book Discussion – [06:13–10:26]
- Book Reading: “South Africa” Poem – [10:00–10:26]
- Breakups, Journaling, and Growth – [14:07–18:21]
- Self-Reliance & Healing – [18:38–21:33]
- Drama Triangle and Relationship Patterns – [27:16–31:18]
- Jonas Brothers/Fangirl Chat – [31:18–35:54]
- Taylor Swift, Family, and Resilience – [36:54–41:09]
- Listener Call: Bri on Coworker Crush – [46:46–57:17]
- Listener Call: Lauren on Dating New City – [58:28–65:38]
- Haley’s Boldness in Dating & Advice Wrap-Up – [65:39–71:50]
Episode Tone & Style
The episode’s signature is conversational, irreverent, and honest, with Chelsea’s trademark blunt compassion and playful sarcasm. Haley’s openness, self-deprecating humor, and thoughtful introspection complement Chelsea’s energy, making for a dialogue that is both therapeutic and fun. Both hosts encourage vulnerability, action, and self-love – and they never shy away from sharing their flaws and learnings.
Final Thoughts
"Becoming a Male Lion" isn’t just a metaphor but a manifesto for reclaiming personal power, whether in heartbreak, career, or the search for love. The episode brims with permission to feel, to try, to fail, and to laugh about it all, leaving listeners with both practical advice and a sense of hopeful camaraderie.
Haley’s book "I’m Sad and Horny" is out now.
Chelsea’s High and Mighty Tour tickets on sale.
[For full transcripts and video episodes, find Dear Chelsea on YouTube or visit chelseahandler.com]