The BOB & TOM Show Extra

Episode: Jamie Lissow & Alli Breen with Sexy Time

Date: October 29, 2025

Episode Overview

This Bob & Tom Extra episode blends irreverent comedy and real-life relationship advice, featuring comedian Jamie Lissow and Allie Breen remotely from an airport. The central theme is “Sexy Time,” a segment where the cast addresses listeners’ romantic dilemmas with their trademark banter, humor, and a healthy dose of friendly disagreement. Relationships, jealousy, personal grooming, and the awkward honesty required in love are all run through the group’s comedic wringer.

Key Discussion Points & Insights

1. Jamie Lissow’s Musical Opening

• [02:26–06:07] Jamie performs a humorous, original tune centered on the theme "O C Double D," riffing on affectionate nicknames and playful, mildly risqué wordplay about notable physical features.
• Memorable lyric:
  • “O C Double D, she's got the Amazon swing, like a grapefruit in a sling…” — Jamie Lissow [03:23]

2. Allie Breen Joins from Orlando Airport

• [06:14–06:59] Allie calls in from an isolated airport spot, setting a laid-back, unfiltered tone. Banter ensues about airport lounges and her trying to find quiet, odd spaces (including a massage room).
• Light airport chaos humor:
  • “I thought I could call from here... feels like I'm in the Twilight Zone.” — Allie Breen [06:32]

3. Sexy Time Segment: Listener Relationship Questions

Classic BOB & TOM wit as the hosts debate, roast, and advise on relationship scenarios submitted by listeners.

A. 38-year-old Girlfriend Gets a Tramp Stamp

• [07:57–11:22]
• Listener wonders if it’s a "red flag" that his 38-year-old girlfriend got a tramp stamp.
• The crew alternates between jokes and genuine takes:
  • “Why wait till you're 38 to get one, though?” — Christopher (Bob Kevoian) [08:18]
  • “I think it's a good idea to wait to get a tattoo… this person's an adult… I almost got a Marvin the Martian tattoo when I was young, like, it would have been insane.” — Tom Griswold [08:48]
• Concerns raised about placement vs. style, and whether partners should comment on each other's tattoos.

B. Boyfriend Has a Female Best Friend—Is it a Problem?

• [12:04–13:28]
• Listener is jealous of her boyfriend's close friendship with another woman.
  • “I know there's nothing sexual going on... I think the emotional thing is even worse. What do you guys think?” — Letter [12:16]
• Josh Arnold’s blunt take:
  • “Get out. Pack a bag.” — Josh Arnold [12:24]
• Group explores the emotional vs. physical boundaries in friendships and relationships, with humor about the use of the word "lover."

C. Wife Keeps Cutting Her Hair Shorter—Turn-off?

• [13:34–16:33]
• Listener laments that his wife’s increasingly short haircuts are making him less attracted to her; wonders if he can comment or if it’s “too controlling.”
  • “Shouldn't the person who's having sex with you have some input about your haircut?” — Letter [13:58]
• Tom shares a personal anecdote:
  • “I yield to her for all things physical. Yeah, sure... even haircuts.” — Tom Griswold [15:04]
• Group consensus: each partner can have an opinion, but bodily autonomy wins; some suggest wigs for roleplay.

D. Man Buys His Ex-Wife Jewelry—Too Friendly?

• [16:59–18:09]
• Listener is uncomfortable that her boyfriend buys his ex-wife (and their daughter) jewelry for their shared birthdays.
  • “Isn’t that inappropriate to get your ex jewelry? Do I bring it up or is that going to make me sound crazy?” — Letter [17:16]
• Mixed reactions:
  • “This letter makes you sound crazy.” — Christopher (Bob Kevoian) [17:21]
  • “Yeah, I think it’s weird.” — Jamie Lisso [17:32]
• Ultimately, group leans toward: It’s weird, but context matters—what kind of jewelry? What’s the co-parenting dynamic?

E. Listener Cheated Twice on Girlfriend—Confess or Conceal?

• [18:15–19:26]
• Listener asks whether to confess to cheating with girlfriend's friend, fearing it may destroy the relationship.
  • “I know it was a dumb thing to do… Do I come clean and tell her?” — Letter [18:19]
• Josh Arnold cynically replies:
  • “Isn't there the school of thought... if you tell someone something like that, you’re really... it’s kind of selfish.” — Josh Arnold [19:02]
• Comedy and caution intermingle; the hosts agree that if it’s likely to come out, confession is best, but recognize it could backfire.

Notable Quotes & Memorable Moments

• On tattoo etiquette:
  “If it says, Oh, by the way, don't be surprised when you look at my... I’ve got an arrow down there that says Kilroy was here and 30 other guys...” — Christopher (Bob Kevoian) [10:14]

• On autonomy and looks:
  “This woman should be able to wear her hair however she wants.” — Female Co-host [16:33]

• On relationships and honesty:
  “When you get it off your chest… when my ex wife told me all this? She didn’t tell me. I read it in her diary.” — Tom Griswold [19:17]

• Smart comeback on confessions:
  “Until her best friend gets mad at her and then she goes, 'Oh well, I slept with your boyfriend twice.' And then that happens.” — Caller or Listener [19:08]

Important Segment Timestamps

• Jamie Lissow’s Song: [02:26–06:07]
• Allie Breen Joins from Airport: [06:14–06:59]
• Sexy Time Letters/Advice Starts: [07:57]
• Tramp stamp letter & tattoos: [07:57–11:22]
• Emotional cheating / best friend scenario: [12:04–13:28]
• Haircut debate: [13:34–16:33]
• Jewelry for ex-wife issue: [16:59–18:09]
• Cheating confession dilemma: [18:15–19:26]

Conclusion

This episode delivers the signature BOB & TOM blend of quick-witted banter and unfiltered relationship advice, as Jamie Lisso and Allie Breen help listeners (and each other) stumble through the complications of modern love. Whether defending the right to questionable tattoos, debating the boundaries of jealousy, or just cracking each other up, the cast offers laughs and the occasional genuine insight—no matter how awkward the subject.

For more "Sexy Time" letters or classic BOB & TOM banter, catch them every weekday morning or subscribe for the commercial-free VIP podcast.