Podcast Summary: Jeff Lewis Has Issues

Episode: Kym Whitley & Caroline Rhea: Pools & Prison Clothes
Release Date: April 3, 2026
Host: Jeff Lewis
Guests: Kym Whitley, Caroline Rhea

Overview of Episode

This episode delivers on Jeff Lewis’s promise of no-filter, comedic chaos, and unfiltered takes on personal drama. Joined by comedians Kym Whitley and Caroline Rhea, the trio dives into tales of messy home renovations, pool drama, prison etiquette, comically disastrous travel stories, and secrets about their everyday lives. True to form, Jeff lets his guests riff, argue, and roast one another while exposing the quirks of fame, friendship, and family.

Key Discussion Points and Insights

1. Kym’s Neverending Pool Saga

• Pool Renovation Fiasco:

  • The group detailed hilarious back-and-forth arguments over Kym’s pool depth, pool men disasters, and the saga of deciding between safety rails and step heights.
  • Quip: Kym jokes about her “cinnamon roll” breasts as flotation devices, the difficulties of getting her hair wet, and the ongoing retrofitting of the pool to satisfy each new wish.

• Debate Over Pool Guy Quality:

  • Relatable “bad pool guy” stories turned into a frustrated competition about who had it worst.
  • Jeff: “You better fire that pool man because he is not gonna… I mean, this is… we’re doing Pebble Tech… I don't want your pool man to ruin it.” (04:20)
  • Insight: Maintaining a pool is surprisingly expensive and difficult, with Jeff describing his pool as “having a mortgage.”

• Decision Fatigue and Control Issues:

  • Both Jeff and Caroline discuss Kym’s indecisiveness and need for control, calling her out—humorously—on second-guessing every renovation.
  • Caroline: “She has, like, a selective memory. So right now, I'm telling you live on the radio, tomorrow, your tile is going in at 7am.” (14:01)

• Safety Hazards:

  • The hosts crack jokes about steps so steep “you fall,” and Kym’s desire for a discreet, emerging handrail.
  • Jeff (sarcastically): “How about something that guarantees you'll be electrocuted the minute you get in the pool? How about a lightning rod?” (15:26)

2. The Gift Basket – Prison Themes & Comedic Banter (10:00–13:00)

• Unboxing the Gift:

  • The trio delightfully unpacks a gift basket filled with luxury and oddities: caviar, sardines, mustard, chapstick, liquor, and even magnum condoms—prompting ribald humor.
  • Kym: “The prisoners, they eat sardines with crackers and mustard. So I felt like instead of your caviar, you needed to get with the people.” (10:49)

• Notable Quote:

  • Jeff (re condoms): “God, I haven’t used those in years.” (11:31)
  • Caroline: “Can I borrow the safety pin?” (11:58)

• Underlying Insight:

  • The prison theme sets up a segue to tales about dating ex-inmates, prison fashion faux pas, and the sometimes absurd etiquette for prison visitations.

3. Prison Visits, Clothes, and Dating (23:00–29:00)

• Prison Visitation Wisdom:

  • Caroline recounts being admonished for wearing “too tight” pants when visiting a male prison.
  • Caroline: "They said, your pants are too tight. And he’s smiling at me, me, 100%. They are in no way provocative." (27:13)

• Dating Prisoners:

  • Kym admits to dating men who later went to prison (for conspiracy/drugs)—sharing how she’d send care packages of sardines, crackers, and mustard.
  • Kym: “I didn't date them. When they came out, they went in and then they were a prisoner. That's how I know about sending the care package.” (24:20)

• Prison Etiquette:

  • Informative and hilarious: tight clothes are a no-go, and visitors often end up shopping at Kmart to change.
  • Guests joke about needing "prison boxes" and care packages, and Caroline riffs on being recognized from Sabrina the Teenage Witch by prison guards.

4. Friendship, House Chaos, and Maximalist Living (17:00–21:30)

• House Design and “Stuff”:

  • Jeff and Kym good-naturedly roast Caroline for being a hoarder or maximalist; Caroline defends her curated style.
  • Kym: "Mine are browns and muted colors. Hers are pinks and yellows. You walk in and you're just like, it's beautiful." (17:58)

• Blind Interior Designer Revelation:

  • Caroline reveals her art hanger/designer is legally blind—which, after initial disbelief, is marveled at for her unique talent.
  • Caroline: “Colette is legally blind, and she's the most talented... She does all of this. How does she do it? I don't know!” (22:04)

5. Hilarious Italy Vacation Disasters (35:00–41:00)

• Adventure & Mishaps:
  • The pair relive an Italian vacation, including hat store escapades, suspicious passport white-out, oddball tour guides, and scorpion-filled villas.
  • Caroline (passport): “You put white out on your passport?"
  • Kym (nonplussed): "Absolutely. Why you need to know how old I am?” (36:06)
• Scorpions and Avoidance:
  • Kym is so scared she watches "Shark Tale 3" in her room instead of sightseeing.

6. Parenting & Sneaky Eating (48:17–49:20)

• Kym’s “Mom Guilt” Tricks:

  • Kym confesses to eating fast food in the garage so her son Joshua won’t ask for it, and jokes about “anti-chicken spray” to hide the evidence.
  • Jeff and Kym share strategies for avoiding “parental food theft” detection.
  • Kym (on Chick-fil-A): “Pull in the garage, eat it real fast. Then you have to spray because if they smell the chicken on you...” (49:18)

• Wallet Theft at School:

  • Joshua’s wallet is stolen at public school; the teacher offers little sympathy.
  • Kym: “She said, yeah, it’s supposed to get stolen. ...That’s what the teacher told him.” (48:21)

7. Tour Dates and Comic Closer (46:07–48:02)

• Both comedians promote upcoming dates, riffing about the exhaustion and absurdity of road comedy at their age.
• Caroline: “If there are any twin men in their late 90s, preferably a terminal illness that won’t cause them any pain, that would like to marry us so we can stop doing this road work...” (46:30)

Notable Quotes & Memorable Moments

• On Pool Depth Fights:

  • Caroline: “Hers does. There, that.”
  • Jeff: “Okay, but we’re not seeing nipple, Kim. ...The nipple's tucked under. It's rolled up like a cinnamon bun. When you get old, that's what happened. Just roll them on up.” (02:06)

• On Prison Clothing:

  • Caroline: “I spoke quite extensively to the prison stylist before I arrived here... they go, don't wear a white cotton shirt or khaki pants. And I said, I won't, because I don't work for Southwest Airlines.” (25:30)

• On Comedy Career Fatigue:

  • Caroline: “We work for FedEx.” (47:38)

• On Parenting:

  • Kym: “Pull in the garage, eat it real fast. Then you have to spray because if they smell the chicken on you...” (49:18)

Timestamps for Key Segments

• Pool Renovation Drama: 02:21–17:00
• Gift Basket Unpacking (Prison Theme): 10:00–13:00
• House Design, Hoarding, and Friendship Roasting: 17:00–21:30
• Blind Interior Designer Revelation: 21:50–22:18
• Prison Visitation & Dating Stories: 23:00–29:00
• Italy Vacation Stories: 35:00–41:00
• Parenting, School Theft & Sneaky Eating: 48:17–49:20
• Tour Date Banter: 46:07–48:02

Tone and Language

The episode’s tone is irreverent, fast-paced, and playful, buoyed by three personalities who embrace roasting, self-deprecation, and sharp observational humor. Comedic exaggeration and improv keep the conversation lively. The language is casual, R-rated, and as candid as the “issues” demand.

For new listeners:
This episode captures the heart of Jeff Lewis Has Issues: real-life mess meets comic therapy. Whether you’re eyeing a pool reno nightmare, curious about prison etiquette, or just in need of a hearty laugh at the chaos of friendship and family, this one’s a treat.