The BOB & TOM Show Free Podcast

Episode: BT Extra: Alli Breen with Sexy Time

Date: September 18, 2025

Episode Overview

This BOB & TOM Extra brings comedian Allie Breen to the “Sexy Time” segment, where the team field listeners’ questions and letters about love, relationships, and sexual dilemmas with their signature bawdy humor and honest, unfiltered advice. The banter is wild as ever, with generous doses of sarcasm and tongue-in-cheek wisdom, ensuring both entertainment and the occasional nugget of real advice for those navigating modern romance.

Key Discussion Points & Insights

1. Mother-In-Law Oversharing About Conception

[04:33 – 08:44]

• Letter: A woman writes that her mother-in-law is heavily involved in her and her husband's efforts to start a family, offering intimate advice on positions, timing, and even food, which she finds creepy.

• The Panel Reacts:

  • Tom and Chick Magee debate whether this is “cute” or way too invasive.
  • Jokes about standing on her head and saying the Lord’s Prayer (“Well, your mom said after we’re done banging, I’m supposed to stand on my head...” – Tom, 05:22) hit the table.
  • Boundaries are discussed—panel agrees there’s a line the mother-in-law has crossed.
  • “Her mother-in-law is suggesting sexual positions. That is ... yeah, that would be uncomfortable.” (Allie Breen, 05:53)

• Memorable Banter:

  • “You are not mature enough to have kids is what I'm going to say.” (Tom, 08:23)
  • Lively argument about what's more creepy: a mother talking to her daughter-in-law or to her son about sex.

2. Destination Wedding, Destination Disaster

[09:42 – 11:34]

• Letter: Woman’s boyfriend invites her to a destination wedding in the Bahamas, but expects her to pay her way after making it sound like he’d cover everything. She’s only been dating this guy for four and a half months and knows no one else at the event.

• Advice & Humor:

  • General consensus: If you invite someone, you should cover the cost.
  • “If he pays, she better be putting out. That is a contract, okay?” (Tom, 10:40)
  • Allie suggests: “I can’t afford to go, but I’d love to. So if you want to help me out, that’d be great.” (Allie, 10:26)
  • The group scorns destination weddings as “infuriating.”

3. Secret Baby Daddy Drama

[11:34 – 15:31]

• Letter: “One of my best friends is pregnant, but won’t tell anyone who the father is. It’s causing a stir—now we all suspect it’s one of our husbands.”

• Panel Reactions & Laughter:

  • “I hope this is on Netflix. I want to watch.” (Tom, 11:50)
  • Discussion spirals into wild scenarios: “Wouldn’t you think she would tell someone who’s potentially the dad?” (Allie, 13:35)
  • “There should be a big reveal—like a gender party, but for which husband’s the dad.” (Tom, 14:02)
  • “The thing that I find amazing is that they still call her a friend if they think she's screwing their husbands!” (Tom, 14:06)
  • Jokes about DNA-testing, reveal parties, and the wild drama that would ensue.

4. “Beaches” for Benefits—Transactional Fun

[15:31 – 18:14]

• Letter: A woman details a “Friends with Benefits” situation centered on sexual favors (“beaches”) traded for gifts and dinners. Now, the man has a girlfriend but wants the arrangement to continue; she’s unsure whether to keep it going, especially since it’s becoming transactional.

• Panel’s Candid Take:

  • “You’ve gone pro, and it’s only a matter of time before you’re just doing it for cash.” (Tom, 16:48)
  • “This is where I wish it was the Ann Landers thing, so she’d write back: ‘Dear whore, in Walla Walla...’” (Tom, 16:56)
  • Suggestions to “up the ante,” and even a quip about blackmail.
  • Discussion on how transactional sex morphs into something else: “Now he has a girlfriend, but we’re still in this situation. I told him he’s cheating on his girlfriend and he says he’s not.” (Letter, 16:32)
  • Debate gets sillier: “What’s an expensive purse, Christy?” “Birkin!” (17:59)

5. Girlfriend Who “Goes For The Jugular”

[18:20 – 19:21]

• Letter: Man laments his hot girlfriend’s cruel comments when they fight (“look at me and look at you—you should be grateful to be with me”) and insults about him not being good enough.

• Advice & Reactions:

  • “Get out. Get out. Now. That’s the way she actually thinks.” (Tom, 18:33)
  • “What a combo. Mean and lazy. But she’s hot.” (Tom, 18:59)
  • General consensus: Don’t settle for someone treating you poorly, hot or not.

Notable Quotes & Memorable Moments

• “Her mother-in-law is suggesting sexual positions. That is ... yeah, that would be uncomfortable.” — Allie Breen [05:53]
• “You are not mature enough to have kids is what I'm going to say.” — Tom [08:23]
• “If he pays, she better be putting out. That is a contract, okay?” — Tom [10:40]
• “There should be a big reveal—like a gender party, but for which husband’s the dad.” — Tom [14:02]
• “You’ve gone pro, and it’s only a matter of time before you’re just doing it for cash.” — Tom [16:48]
• “Mean and lazy. But she’s hot. What a combo.” — Tom [18:59]

Timestamps for Important Segments

• [03:27] Alli Breen calls in from Mohegan Sun; intro to Sexy Time
• [04:33] Letter 1: Mother-in-law advice on conception
• [09:42] Letter 2: Destination wedding and money expectations
• [11:34] Letter 3: Secret baby daddy and group suspicion
• [15:31] Letter 4: Transactional “beaches for benefits” dilemma
• [18:20] Letter 5: “Hot, mean, and lazy” girlfriend

Episode Tone & Style

The episode is frequently raunchy, fast-paced, and packed with sarcastic jabs, mock seriousness, and laughs. The hosts don’t hold back, freely mixing humor and honesty, often pushing the boundaries, but still delivering solid advice hidden amidst the punchlines. Allie Breen serves as the straight-talking, empathetic center, surrounded by the irreverent BOB & TOM gang.

Summary

Listeners can expect a blend of genuine relationship advice and comedic, often outrageous commentary on the challenges of romance, sex, and modern dating. Alli Breen’s “Sexy Time” segment is a spirited, anything-goes discussion—equal parts laughter, mockery, and real talk about love’s messiest dilemmas.