The HoneyDew with Ryan Sickler #365 — Jessica Michelle Singleton

Main Theme / Purpose (03:12)

This episode of The HoneyDew features comedian Jessica Michelle Singleton. Staying true to the show’s mission—“highlighting the lowlights”—Jessica shares raw, darkly humorous stories from her turbulent upbringing. The discussion covers family secrets, parental trauma, surviving Alaska, grappling with identity, and the resilience required to grow up under trying circumstances. Dry wit and candid reflection set the tone, celebrating the ability to laugh at life’s heaviest moments.

Jessica’s Background: Music, Comedy, and Country Roots (04:12–07:00)

• Jessica plugs her new special "Hi, y’all," her podcast ("Hey, Idiots"), and her country music alias, Norma Lee Wild.
• Admits to hiding her love for country music while living in California but embraced it during the pandemic by releasing songs (05:10).
• She and Ryan bond over old-school country music, referencing Stagecoach festival and artists like George Strait.

“Some people hear country music, they think it’s shifting now... People go, ‘What, your cousin?’ and you’re like—I mean, I tried! What do you want me to do? He said no.” —Jessica (05:49)

Family Origins: Mississippi, Germany, and a Waffle House Trauma (07:00–13:40)

• Jessica was born in Germany while her father served in the Air Force, then moved to Mississippi, settling in Ocean Springs (07:12–08:24).
• Her family life featured domestic violence, addiction, loud fights, and police visits—normalized until she noticed other families acted differently (09:03–13:05).
• Her father became addicted to meth after military retirement and may have been involved with the “Dixie Mafia.”
• Major memory: At age eight, Jessica’s father abandoned her at a Waffle House during a one-on-one outing (09:59–12:26).

"He just went to the car, drove away... I saw him drive away and was like, oh, I’m sure he’ll be back.” —Jessica (11:12)

• Community members recognized her and gave her a ride home; Jessica repressed the memory until adulthood, realizing its significance much later.

“Not My Biological Dad”: The Sperm Donor Bombshell (13:40–34:44)

• During her college years, Jessica learns—via a drunk stepbrother’s slip—that neither she nor her brother are the biological children of the man they knew as their father (16:37–17:54).
• Both were conceived at a Beverly Hills sperm bank due to their dad’s Klinefelter syndrome (XXY), which left him infertile and caused significant physical effects (19:10–20:25).
• Jessica discovers her true lineage through 23andMe: She’s predominantly Ashkenazi Jewish, not German/Irish as raised (17:22–18:07).

"When you were born, the first thing I said was, she looks like an ugly Jew baby." —Jessica’s mom (18:07, quoting her mother)

• Her brother’s donor is different (British, not Jewish), making them half-siblings. Jessica grapples with identity, genetic health risks, and the sense of family legacy.

Confronting Parents with the Truth (33:00–34:44)

• Jessica first broaches the sperm donor discovery with her dad, who is ultimately accepting; then with her mother, who confirms it but never told her brother (33:03–33:29).

“Are you going to tell my brother? ... ‘Your mother and I agreed we were never gonna tell you guys.’” —Jessica (33:12)

• Dark humor surfaces as Jessica reflects on which genetic traits she inherits: “At least I don’t have the leave-your-kid-in-a-Waffle House gene.” (34:23)

The Sharp Edges of Alaska Life (41:01–60:54)

The Move North (41:01–43:39)

• After her father left, Jessica’s mother—newly sober but struggling—relocated the family to Anchorage, Alaska, for a government job (41:15).
• The drive out of Mississippi was rushed due to an impending hurricane that ultimately destroyed Jessica’s old bedroom the night after they left (44:33).

“The storm came in, smashed through our house, smashed through my bedroom. I would have died in the night.”—Jessica (44:33)

The “Brady Bunch” Family and School Instability (45:43–47:54)

• Her mom marries Terry, a man she met in AA (and who was missing a finger). They form a blended family with stepbrothers, prompting Jessica to attend four different sixth grades in one year (47:10).

Violence, Mental Illness, and Tragedy in Alaska (49:09–61:03)

Murder and Loss

• Multiple classmates and friends died violently in high school:
  • Friend Delaney was murdered by a peer; Jessica recounts the trauma of the search parties and seeing her killer on “MSNBC Lockup” years later (50:01–53:52).
  • Three brothers she befriended were executed by their paranoid schizophrenic mother, who confessed calmly to police after waiting in the house with their bodies (54:18–57:27).

“That’s a different kind of crazy.” —Jessica (58:12)

• Other friends: One stabbed over a case of beer, one drowned in a swimming pool (59:56–60:33).
• Jessica notes the high prevalence of death and instability fueled her dark sense of humor.

Coping and Reflection

• She escapes Alaska via college in Florida, a move partly to be nearer to her estranged father (60:54).

Life Afterward: Survival, Resilience, and Advice (61:03–65:22)

• After Jessica left for college, her mother took government contracting jobs worldwide, later settling in Baltimore and eventually retiring (61:03–62:13).
• Jessica maintains a relationship with her mother, embracing the dynamic with humor and boundaries.

“You wouldn’t be funny if I was a better mom.” —Jessica, quoting her mother (61:31)

Advice to Young Self & Others (63:00–64:59)

• Jessica’s advice to her 16-year-old self: “Just keep going... Lean on people... Reach out, ask for help.”
• Ryan underscores this point: breaking the trauma response of hyper-independence, learning to trust and accept help.

“You’re not a burden for needing help.” —Jessica (64:42)

Notable Quotes & Moments

• “Left alone in a Waffle House at eight years old”—Jessica (10:38–12:26)
• “At least I don’t have the leave-your-kid-in-a-Waffle-House gene.”—Jessica (34:23)
• “It’s Alaska. You get nine months of winter... winter, still winter, still winter, and then construction.”—Jessica (44:41)
• “My woods in Alaska—bear, murderers, or just a man with an axe... never ran into one, but surprisingly.”—Jessica (49:10)
• “Had three friends who were brothers; their mom killed all of them.”—Jessica (54:18)
• “You're not a burden for needing help.” —Jessica (64:42)

Key Timestamps

• 03:12: Episode starts, Jessica Michelle Singleton introduced
• 07:12: Jessica’s early life—born in Germany, moved to Mississippi
• 09:59: Father's drug use, abandonment at Waffle House
• 16:37: Discovery she was conceived via sperm donor
• 17:54: 23andMe reveals Jewish ancestry; mother’s brutal honesty
• 33:03: Confronting parents about her lineage
• 41:15: Move to Alaska, new beginnings (and more family chaos)
• 44:33: Escape from hurricane, brush with death
• 50:01: Friends lost to violence; Delaney’s murder and MSNB Lockup cameo
• 54:18: Schizophrenic mother murders three friends
• 60:54: College escape, family spreads out
• 63:00: Advice to her younger self
• 65:08: Final plugs and wrap-up

Closing Thoughts

Jessica Michelle Singleton’s episode is a heavy but laugh-out-loud journey through the pain, confusion, and oddities of family history. From being abandoned in a Waffle House to discovering hidden genetic heritage and surviving a series of tragedies in Alaska, Jessica’s storytelling—laced with dark humor and honesty—embodies the “HoneyDew” principle that the most challenging moments often make us who we are.

For follow-up:

• Watch Jessica’s special, “Hi, y’all”
• Listen to her podcast “Hey, Idiots”
• Check out her country music as Norma Lee Wild