The BOB & TOM Show Free Podcast

Episode: B&T Extra: Sexy Time with Alli Breen
Date: September 11, 2025

Overview

This B&T Extra episode is devoted to "Sexy Time with Alli Breen," where the cast dishes out comedic relationship and life advice. Recorded in classic Bob & Tom style, the episode blends humor, playful roasting, and a mix of real talk and absurdism as they navigate listeners’ letters about romantic dilemmas, etiquette, and personal quirks. The banter centers on modern dating, cosmetic enhancements, awkward work situations, and tipping protocol, all with Alli Breen’s wry, New York City–flavored insight at the core.

Key Discussion Points & Insights

1. Luggage Technology & Travel (03:00–07:50)

• The team humorously debates the "discovery" of suitcases with four wheels.
• Tom remarks on how revolutionary spinner suitcases are for him, prompting laughter as others point out they've existed for ages.
• Discussion pivots to travel upgrades and simple tech that took too long to become mainstream.
• Notable insight: Need for "wheel locks" on suitcases for slopey surfaces remains unmet.

Quote:
"This is insane. It's like he just woke up from a coma." — Alli Breen (04:51)

2. Botox, Fillers, and Relationship Honesty (08:58–12:27)

• A listener asks what to do about his wife’s ever-increasing use of Botox/fillers.
• The cast references Lauren Sanchez’s much-dissected appearance as shorthand.
• Alli and crew discuss how beauty routines can spiral and ways partners might “gently” intervene.
• Alli shares her own history with Botox and the rush of hindsight clarity when stopping.

Advice given:

• Use old photos as a gentle nudge for self-reflection.
• Point out mutual friends who might be “overdoing it” as a cautionary tale.

Quotes:

• “It’s just like when you're tanning...you’re never tan enough. Once you start...you gotta keep going. Eventually you’re like, dude, you look weird.” — Alli Breen (09:51)
• “Hold up a picture ... look how beautiful you are, you’re starting to not look like you.” — Alli Breen (10:32)
• "Guys prefer women natural rather than all—I do." — Christopher (12:00)

3. Workplace Infidelity: Should You Tell? (13:49–14:54)

• Letter: Should an employee tell a wife that her husband (a co-worker) is apparently having workplace affairs?
• Responses are swift and practical: mind your business, don’t get drawn into drama, and skip the heroics.
• Jokes veer briefly into blackmail and free food as (comedic) alternatives.

Quotes:

• “Eat your veal parmesan and get out.” — Christopher (14:34)
• “Maybe a tiramisu ... a bottle of wine to take home!” — Christopher (14:54)
• “The key here is blackmail ... tips and blackmail. Tax free.” — Christopher (14:44)

4. First Date Etiquette: Who Pays (15:08–16:58)

• Listener scenario: She offered to split the lunch bill and pay the tip; he let her pay the tip, leaving her annoyed.
• The crew discusses shifting gender roles, modern dating confusion, and unspoken social contracts.
• They conclude that men are just trying to follow evolving expectations, and overthinking the “game” leads to miscommunications and frustration.

Quotes:

• "Men are kind of being told ... to listen to women when they say something." — Christopher (15:38)
• “Mouth shut if you don’t want to ... mind games. The first date.” — Alli Breen (16:14)
• “Sorry you had to leave a tip on a $40 bill. I hope you get that $8 back.” — Christopher (16:40)

5. Tipping Etiquette (16:57–18:45)

• Alli and others share stories of secretly supplementing poor tips after dates or family outings.
• They debate outdated rules (not tipping on alcohol/tax) and the unfair burden of tipping in service industries.

Quotes:

• “I have gone back in and said I have to use the bathroom, and gave a little more money.” — Alli Breen (17:31)
• “Why wouldn’t the restaurants just pay them more too? ... It's kind of antiquated.” — Alli Breen (18:45)

6. Memorable & Comedic Asides

• Artichoke/Vaginal Joke (02:52–03:19): A running joke comparing artichokes to Georgia O’Keeffe's paintings and vaginas, leading to goofy exchanges.
• Frame a Tattoo (13:18–13:37): Off-topic quip about making art from your deceased partner’s tattoo.
• Grass-Fed Dating (17:07–17:12): Confusing “grass-fed” with “free-range” to describe single life.

Notable Quotes (with Timestamps and Attribution)

• “It’s like he just woke up from a coma.”
  — Alli Breen on suitcase wheels (04:51)

• “You look like an idiot. Just tell her that.”
  — Alli Breen on cosmetic honesty (09:48)

• “Maybe she knows and doesn’t care.”
  — Alli Breen on infidelity at work (14:19)

• “Eat your veal parmesan and get out.”
  — Christopher on staying out of workplace affairs (14:34)

• “Men are kind of being told ... to listen to women when they say something.”
  — Christopher on dating etiquette confusion (15:38)

• “I have gone back in and said I have to use the bathroom and gave a little more money.”
  — Alli Breen on supplementing bad date tips (17:31)

Timestamps for Important Segments

• [02:52] — Kicking off with the artichoke/O’Keeffe joke
• [03:30]–[07:50] — Suitcase wheels/luggage tech banter
• [08:58]–[12:27] — Letter: Botox/Filler interventions and relationship honesty
• [13:49]–[14:54] — Letter: Workplace infidelity and the “do I tell her?” dilemma
• [15:08]–[16:58] — Letter: First date bill and tipping etiquette
• [16:57]–[18:45] — Poor tippers, tipping rules, and restaurant practices

Takeaways & Tone

• Advice is always delivered with a wink: even the practical suggestions are laced with sarcasm and playful exaggeration.
• No easy answers: Modern life and relationships are messy; the show is strongest when turning that mess into punchlines.
• Alli’s role: She balances New York cool, candor, and self-deprecation, always willing to share her own missteps to illustrate a point.

For fans of sharp, irreverent humor with real-life dating dilemmas and some surprisingly practical advice, this is classic Sexy Time with Alli Breen.