Transcript

Katherine (0:00)

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Chelsea Handler (0:04)

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Ross Matthews (1:06)

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Chelsea Handler (1:36)

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Dr. Wellington Garcia Matthews (1:43)

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Chelsea Handler (1:48)

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Chelsea Handler (1:58)

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Chelsea Handler (2:05)

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Summary

Dear Chelsea – "Tio & Tio with Ross Mathews & Wellinthon Garcia-Mathews"

Episode Date: December 11, 2025
Host: Chelsea Handler
Co-host: Katherine Law
Guests: Ross Mathews (TV host/producer, author) & Dr. Wellinthon Garcia-Mathews (educator, Ross’s husband)

Episode Overview

This episode of "Dear Chelsea" brings together comedian Chelsea Handler and her guests, Ross Mathews and Dr. Wellington Garcia-Mathews (recent children’s book co-authors and married couple), for candid, spirited discussions about relationships, growth, joy, vulnerability, LGBTQ+ family dynamics, and following your own timeline. The crew fields advice calls from listeners, sharing wisdom and wit about intimacy, creative burnout, and being seen for who you truly are.

Key Discussion Points & Insights

1. Ross & Wellington: Life Changes, Openness, & Home

[06:02 – 11:30]

Chelsea reflects on her long friendship with Ross, who recounts meeting Wellington in Puerto Vallarta and how a vacation romance led him to uproot his Palm Springs life and move east.
The couple talks about finding home and redefining life together, with Ross noting:

"You put a saddle on life and just see where it goes. And so that’s what I did. Yippee. And that brought me here." (Ross, 07:25)
Discussion about becoming more settled (bedtime routines, liking the countryside, early dinners), and how aging means embracing the habits and quirks that fit you best, not fighting what feels right.
On letting life surprise you:

"I think people are so rigid in what they think they should be doing or who they think they should be...and that is exhausting to me." (Ross, 11:16)
Wellington adds: "I’m all about just getting rid of all that and just doing what you need to do for yourself and whatever makes you happy." (Wellington, 11:58)

2. The Children’s Book: "Tio & Tio"

[12:30 – 16:57]

The couple shares the inspiration behind "Tio & Tio," based on their nephews’ role as ring bearers at their wedding.
Wellington (an educator) shaped the book to help kids understand their importance in the family, and added sophisticated vocabulary to spark rich parent/child and classroom conversations.
"As a teacher ... it’s important to ensure that we have vocabulary in there ... the best way to get kids to motivated to actually read is teaching them background knowledge." (Wellington, 15:53)

3. On Changing Plans, Growth, and Being Open to Life’s Twists

[16:57 – 18:25]

Wellington speaks about blending lives after Ross relocated, emphasizing empathy and authenticity in relationships.
"It was important for me to have him really grounded...to feel like this is his home. I know how much he’s left..." (Wellington, 17:16)
On Ross’s positive influence: "There’s a reason why he always makes me laugh, no matter what. That’s our love language." (Wellington, 18:25)

4. Positivity, Mood, and How You Respond to Life’s Letdowns

[19:01 – 20:44]

Ross and Chelsea agree that keeping a sense of perspective and humor is crucial.
"If something sucks, we can say it sucks...but right away, pivot to what can we do to make it better." (Ross, 19:01) "There’s two ways to handle everything...it’s hard to remember that sometimes." (Chelsea, 20:36)

Listener Advice Calls

5. Call #1: Joey – Emotional Mismatch in Partnership

[35:29 – 41:50]

Joey, a 39-year-old bartender and recovering addict, seeks help handling frustrations with his emotionally reserved partner, a firefighter.
Key advice:
- You can’t force someone to work on their emotions; you either accept them or recognize the relationship may be mismatched.
- Chelsea cautions against "spiritual narcissism"—working on yourself doesn’t entitle you to demand the same from others if they’re content.
- Ross’s relatable metaphor:
  
  "If you were renovating your kitchen...you wouldn’t go into someone else's kitchen and tell them they need to renovate it." (Ross, 38:54)
On how ketamine therapy helped Joey see himself more kindly:

"Ketamine just, like, disassociates you from yourself...you can see what other people see." (Joey, 39:40)

6. Call #2: Heather aka Bamaslamading Dong – Burnout from Drag Performance

[43:30 – 49:51]

Heather, a cis woman who discovered confidence and community through drag, finds herself burnt out post-COVID and asks whether to walk away.
Ross validates how challenging drag can be and affirms:

"Drag has brought a lot into your life...what it brought you is still there, whether you're in drag or not." (Ross, 45:59)
Chelsea suggests taking a break, describing how distance from stand-up comedy helped her find new creativity:

"If you’re not feeling something, you shouldn’t struggle with it...take a break and walk away." (Chelsea, 47:44)

7. Call #3: Cassidy – Girlfriend’s Difficult ‘Coming Out’ Dynamics

[56:01 – 61:13]

Cassidy’s girlfriend is coming out to family, but her oldest sister pressures her to keep the relationship secret from their parents.
Chelsea encourages boundaries (don’t go as just a "friend," don’t catastrophize), but Ross advocates for a harder line:

"If my very existence is an issue that you’re going to let your sister dictate, then we have a real problem here. It would be a dealbreaker..." (Ross, 58:20)
Wellington echoes:

"You have to be authentic...and the fact that she’s not allowing her to be part of the picture is problematic." (Wellington, 58:45)
The group agrees: authenticity and dignity come first; don’t accept being "put on mute" to please others.

Notable Quotes & Memorable Moments

On getting older:

"I've lived my life as an active senior since I was young. You know what I mean? I love a sensible shoe." (Ross, 10:10)
Chelsea on personal strength:

"When I turned 50 this year, that was like, OK, I’m a woman—a full fledged woman. There’s a different maturity. I’m not responsible for your feelings. I don’t overthink things. I’m unshakable at this point." (Chelsea, 32:42)
On creative process:

"You’re not just going to start doing something and be amazing at it. ... You have to put in the time to get the results." (Chelsea, 51:11)
On being proud even when no one’s looking:

"I like the decisions I make when no one’s watching. Like, I’m proud of who I am when nobody is looking or watching." (Chelsea, 33:33)

Timestamps for Key Segments

Ross & Wellington’s backstory and relocating: 06:02 – 11:30
"Tio & Tio" book inspiration: 12:30 – 16:57
Adapting, openness, and growth: 16:57 – 18:25
Attitude and perspective on life: 19:01 – 20:44
Joey's call: emotional mismatch in couples: 35:29 – 41:50
Heather's call: drag burnout and creative process: 43:30 – 49:51
Cassidy's email: coming out, dignity, boundaries: 56:01 – 61:13

Tone & Style

The tone is blunt, warm, irreverent, and encouraging. Chelsea, Ross, and Wellington share honest, sometimes ribald humor while centering self-compassion and growth. They're quick to poke fun at themselves, swap stories about aging and quirks, and champion listeners to be authentic and keep moving forward, even if that means taking a break or changing direction entirely.

Conclusion

This “Dear Chelsea” episode is a lively, relatable deep dive into love, change, boundaries, and self-acceptance. Through friendship, romantic partnership, and kaleidoscopic family structures, Chelsea, Ross, and Wellington remind us all: stay open, don’t settle for being muted, and if you need to pivot, do it joyfully—and maybe with some help from a good hypnotist or a great children’s book.