The HoneyDew with Ryan Sickler

Episode 349: Kym Whitley – Surprise Motherhood
Release Date: September 1, 2025

Episode Overview

In this memorable episode, comedian and actress Kym Whitley joins Ryan Sickler to share her unique and heartfelt journey into surprise motherhood. The conversation highlights the lows and unexpected turns of Kym’s personal life, her unconventional adoption story, reflections on relationships and career, as well as insights into raising her son Joshua with love, humor, and a devoted chosen family. The episode weaves in jokes, wisdom, family anecdotes, and the honesty and bittersweet laughter characteristic of The HoneyDew.

Key Discussion Points & Insights

Kym’s Background and Early Life

[08:52]

Kym was born in Cleveland, Ohio, later lived in Sudan (Kartoum) for six years during her childhood because her father was building schools as an architect.
She attended British schools, even developing an accent erased quickly after returning to Cleveland.
Two brothers (and a close cousin treated like a brother).
Her mother was a school teacher before she was born, then became a housewife.

Showbiz, Comedy, and Career

[03:04], [04:42]

Kym discusses her path in comedy, emphasizing that while she doesn’t love stand-up as some of her peers do, she thrives onstage and especially enjoys hosting gigs.
Memories of working on shows like "The Parkers" and "Curb Your Enthusiasm" (notably, her pivotal role in the “Carpool Lane” episode).
Quote:
“Everyone talks about me, I complain and complain...until I hit the stage. Once I hit the stage, it is on and cracking.” — Kym [03:16]

The "Long Shot" Story—Comedy Saving a Life

[05:38]

Ryan recounts how Kym’s "Curb Your Enthusiasm" episode inadvertently provided evidence that exonerated a wrongfully accused man, a story detailed in the Netflix doc "Long Shot."
Kym reflects on the fateful convergence of comedy and justice:

“It always comes back to the clowns.” — Kym [07:54]

Relationships & Decisions

[13:13], [13:44]

Honest discussion about her romantic history: Seven engagements, no marriages.
Explains her hesitancy: fear of losing independence, concerns over finances, and self-doubt about being a good wife.

“Seven rings, baby.” — Kym [13:41]
“I was afraid of a lot of things… not being a good wife. I was just afraid.” — Kym [13:53]
She playfully laments not marrying for money, but appreciates her independence in the end.

The Remarkable Story of Surprise Motherhood

[17:55]

Kym details how, in her 40s, she became a mother overnight:

“A girl who I was close to had him, left him at the hospital, and put my name and number on his toe.” — Kym [18:00]
She gets a call from a hospital social worker: a friend has given birth and left the baby for Kym, who has only two hours to prepare for a newborn.
Emotional and humorous family response—her mother’s blunt advice to "go get that baby" because, as she notes:

“You ain’t got no man. You ain’t got no kids… and you old.” — Kym’s mom [21:26]
Kym navigates the logistics of sudden motherhood: dashing to buy a car seat and bassinet, getting a crash course in baby supplies.

[29:10]

Dive into challenges of legal adoption: Parental rights, court involvement, navigating the foster care system's red tape.
Kym briefly advocates for policy reforms to extend foster care support and ease homelessness.

Naming Joshua & Chosen Family

[30:10], [32:47]

With little time to decide, Kym prays and chooses the name Joshua for her son.
She emphasizes the importance and blessing of her support network: celebrity and longtime friends step in as godparents, mentors, and extended family—creating a true village around her child.

“I didn’t say, can you babysit them? I said, can you be in his life for the rest of his life? It’s a different kind of ask.” — Kym [38:29]
Ryan highlights the gift that unconditional love creates for Joshua, and Kym reflects on the ripple effect of support.

Adoption, Honesty, and Parenting Philosophies

[44:20]

Kym discusses the critical importance of honesty about adoption: using the word "adoption" from the start to avoid secrecy or betrayal.

“Never hide adoption from a child because… their whole life becomes a lie.” — Kym [44:47]
She explains how Joshua has always known he is adopted and feels "chosen."
Addresses complexities of biological parent connections, foster care trauma, and why she’s waited to allow Joshua to meet his birth mother.

“They will always worry about their mother... just wait until they’re older.” — Kym (court attorney’s advice) [49:11]

Single Motherhood, Dating, and Discipline

[49:55]

Discusses dating as a mom: being cautious which men are introduced to her son, and the importance of providing healthy models for relationships.
Shares humorous anecdotes about exes’ discipline methods (e.g., making Joshua pick up leaves one by one).

Regrets, Reflections, and Life Advice

[42:06], [56:47]

Kym wishes she’d had children younger and given her son a sibling so he wouldn’t be alone later in life.
Fond, funny stories about her mother’s humor and practicality, even regarding her own funeral arrangements.
To her 16-year-old self:
“Have no fear. Do not let fear stop you from anything. Try it all. Except for cocaine.” — Kym [56:52]

Notable Quotes & Memorable Moments

On Adulthood Arriving in an Instant:
“Just hanging out, mom and dad, getting ready to get something to eat… And all a sudden, boom, you’re a mom.” — Ryan [23:59]
On Adoption and Chosen Family:
“Adoption, as he’s 2, 3, I was like, oh, my son’s adopted in front of him... We were chosen.” — Kym [46:51]
On Parenting Regrets:
“I wish then somebody said, you know, you should have a baby during this age... I’m just living life, having a good time. My mother put some reality on my behind.” — Kym [22:02]
On Honest Storytelling:
“Keep your legs closed.” — Kym, with characteristic candor, when asked to advise her younger self [56:47]

Timestamps for Key Segments

[03:16] — Kym’s comedy career & hosting
[05:38] — The “Long Shot” Curb Your Enthusiasm story
[13:41] — Seven engagements, no marriages
[17:55] — Unconventional adoption: "I didn’t have no baby...left him at the hospital and put my name on his toe"
[21:26] — Kym’s mother’s blunt perspective on sudden motherhood
[29:10] — Legal aspects of adoption and foster care system
[30:32] — Choosing Joshua’s name
[38:29] — Assembling Joshua’s “village” of godparents and friends
[44:47] — Adoption philosophy: honest conversations with Joshua
[49:11] — Advice from family court attorneys about biological parents
[56:47] — Advice to 16-year-old Kym

Episode Tone

The hallmark warmth, self-deprecating humor, and raw honesty of both Kym and Ryan shine through—turning a story with the makings of a melodrama into a tale of resilience, laughter, and gratitude. Kym’s candidness, humor, and heart reveal the complexity and beauty of building an unconventional family.

Closing Thoughts

Kym Whitley’s journey into motherhood is extraordinary—a lesson in openness to life’s surprises, the strength of asking for help, and the transformative power of love. The episode is a must-listen for anyone interested in adoption, single parenthood, the comedy hustle, or simply the unpredictable, hilarious turns that life can bring.

Featured Plugs

Kym Whitley’s Podcast: “Two Funny Mamas” (w/ Sherri Shepherd)
Film: "Happy Gilmore 2" (Netflix), "Killing Mary Sue" (Prime)
Upcoming Comedy Dates: Cleveland, Arlington, Jimmy Kimmel Vegas Residency, Washington Comedy Theater
Social Media: @kymwhitley on all platforms

End of Summary

wavePod

349: Kym Whitley - Surprise Motherhood

Summary