BT Extra: Alli Breen with Sexy Time

Summary

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The BOB & TOM Show Free Podcast

Episode: BT Extra: Alli Breen with Sexy Time

Date: September 18, 2025

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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.

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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.

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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.”

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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.

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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)

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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.

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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]

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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

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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.

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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.

Transcript

[A]

Thursday Night Football is on and it's only on Prime Video. Tonight, an AFC rivalry ignites as the Miami Dolphins battle the Buffalo Bills in a heated division showdown. Coverage begins at 7pm Eastern with football's best party TNF. Tonight presented by Verizon. Not a Prime member, Not a problem. Simply sign up for a 30 day free trial. It's the Dolphins and the bills tonight at 7pm Eastern, only on Prime Video. Restrictions apply. See Amazon.com Amazon prime for details. This episode is brought to you by Progressive Insurance. Fiscally responsible financial geniuses, monetary magicians. These are things people say about drivers who switch their car insurance to Progressive and save hundreds because Progressive offers discounts for paying in full, owning a home and more. Plus, you can count on their great customer service to help you when you need it. So your dollar goes a long way. Visit progressive.com to see if you could save on car insurance, Progressive Casualty Insurance company and affiliates. Potential savings will vary. Not available in all states or situations. Welcome back. It's another Bob and Tom Extra. This is Christopher. Not only is the Bob and Tom show live every weekday morning, but every afternoon we'll give you a little extra. In case you missed anything on the big show today, comedian Al Kelly Breen with Sexy time. It's coming up in just a minute. When did making plans get this complicated? It's time to streamline with WhatsApp, the secure messaging app that brings the whole group together. Use polls to settle dinner plans, send event invites and pin messages so no one forgets mom's sample and never miss a meme or milestone. All protected with end to end encryption. It's time for WhatsApp message privately with everyone. Learn [e-mail] A happy song It's a world of buns. It's a world of boobs. It's a world of firm perfect babes and dudes it's for you, it's for me. It's on cable tv It's a porn world after all. They show breasts now in almost all the flicks but the women are mad cause they don't show men from the day you are born you're bombarded with porn. It's a porn world after all everybody It's a porn world after all. It's a porn world after all. It's a porn world after all. It's a porn, porn world. There's a lot of strange ways to make a buck but those porn stars they get paid too much they would sit on the face of the whole human race It's A poor world of. We're just waiting for the cast to actually show up for work. Here's more Bob and Tom. Extra. Hello, Chick Magee. And hello to Allie Breen. Oh, she's somewhere. Are you in your bathroom?

[B]

No.

[A]

Is that a shower curtain behind you?

[B]

No, it's like a curtain curtain. I'm at Mohican Sun. I just had a show last night and it's so hot in New York, I think I'm staying here for the afternoon.

[A]

Ah. Oh. Well, great comedian Ally Breen has joined us. She is our hostess for a segment we call Sexy Time. And is that a bathing suit you've got on?

[B]

No.

[A]

Summertime. Okay?

[B]

Exactly. It's a summer top, you creepy man.

[A]

Did you happen to watch ABC News last night? Ginger Z in a bathing suit. Who do you have a crush on? Ginger Z is. She's a knockout. He's been talking about Ginger Z for a year. Michigan. Why was she in a bathing suit on the news? Well, she was in a bathing suit. In my mind. I really couldn't tell.

[B]

It's so hot. Everyone should be in a bathing suit. Are you guys having a heat wave there, too?

[A]

Yeah, it's a little warm.

[B]

Yeah.

[A]

A little toasty. Now, the way. Name. The name of the show, I should say is Sexy Time. And what we do is we try to help people with their love problems. And you have collected a number of letters today. Let's get to our first one.

[B]

Dear Allie, my husband and I are trying to start a family. He told his mom, and now she's been giving me all kinds of advice. Like the most effective sex positions, what time of day to have sex, what foods I should be eating, and more. It's really creeping me out. Is this normal? My husband thinks it's cute.

[A]

I do, too. I don't know. No, it's not cute to grow up. You're two adult women talking about this. No, but you don't want to envision. Well, your mom said after we're done banging, I'm supposed to stand on my head and say the Lord's Prayer. No, see, that's the problem with today's. Today's world. I blame the Internet. Boundaries. No, this is. We need boundaries. Like the way I have a boundary between you guys. Like I have. I have a shield of lies. You guys are two adults. Get over it. Plus, everything she's saying is baloney. Just do it when you're ovulating. Unless. Unless the mom says, hey, you have sex with him. Like, I don't. That's what he wants. Yeah. Pretty soon you'll have touched it more than I did when I was changing his diapers. No, that's. It's incredibly creepy. No, it's not. Only you are turning it into something sick. She's. She isn't. You do that a lot. Her mother in law is suggesting sexual positions. That is. Yeah, that would be uncomfortable.

[B]

That's weird.

[A]

Get over it. Wow. Hey, look at that. That pepper shaker reminds me of Bill's Johnson. Pass the pepper. Hey, do you shake it like this before you. No. It's awful again. Everything you're doing is adding awful to it. She's not being off. That's my. That's my specialty. Ch. I don't notice that. That's how the show works. I appreciate that. Yeah. I don't know. I think it's wrong. I don't know. How do you. How do you undo it? How do you feel about a girl or a guy either yelling mommy or daddy? Oh, that's not for me. Yeah, I don't care for that either. Right. No, Leave them out of it. I'm out. I don't. I don't care for it at all. Yeah. Yeah. Hey, you're my daddy. What do I have to put you on my phone plan now? What the hell is going on? So I guess in the original letter was the question, how do I get this to stop? Is that.

[B]

Yeah, pretty much. Because she thinks it's creepy. He thinks it's cute. She says, is it normal? She wants it to stop.

[A]

I bet it is normal for mothers in law to sort of insert themselves. It's one thing to be recommending sort of technical things or vitamins or something you can drink or. But not sexual position. Your mother in law installed. What are you talking about? With technical things. I like Altman was saying I don't install cable anymore. WI fi, ovulating and that sort of thing. But still the whole thing is a little bit like, why isn't she giving the advice to just her son? I guess that's just as creepy. Exactly. And then he can tell her to stop because he won't want to deal with it. That's creepier. Yeah.

[B]

Yeah. She should say, well, son from say, tell it to him.

[A]

When you were staying at the house lag, we weakened from the cries I was hearing. You're gonna have to turn her over so it's less creepy if it lands on her back. Oh, for a mother to talk to her blood son. It's still creepy about sexual positions than it is for a mother. To talk to her daughter. They're both creepy. They are not equally creepy at all.

[B]

The sun will put an end to.

[A]

It, though, real quick.

[B]

Yes, that's the point. The son will be like, this is creepy. I don't want to hear this.

[A]

Josh, the distinction you're making is like, well, if I jump out of a helicopter into the ocean from 500ft or I jump into a parking lot, which hurts more. You're missing the point. You're still jumping out of the helicopter because the point is invalid. This lady needs to grow up. Exactly. You're not. You are not mature enough to have kids is what I'm going to say. What if she took that advice? It's off. Children, does your father. Does your father in law. I'm sorry? Does the father in law want to be there for the birthing, by the way?

[B]

The mother in law does for sure.

[A]

It looks like junior's crowning.

[B]

We should start a betting pool on which letter is going to make Josh the angriest.

[A]

By the way, is anybody watching the pit? Yes, we're all watching the effing pit. Stop asking us. In fact, most of us have watched it all the way through. Yes, it's been on for a year. Wouldn't you? But the. The birthing segment is rather graphic. Seven times the kid's head's sticking out and all of a sudden he starts singing. Hello. That was an odd choice. Yeah. Did you not see your children being born? I don't want to see it again. I like them. I like them when they're all out. Okay. I like them when they're all out. Our guest is comedian Allie Breen. You can find her a L L I B R E E N on your favorite social media platform or on OnlyFans Ali B. And you can write her with your love troubles. And as you can see, we're really good at fixing them. What's next, Ally?

[B]

Dear Allie, my boyfriend asked me to go to a destination wedding with him in the Bahamas. I said yes, got excited, figured he'd be paying. But he just sent me all of his flight and hotel information, telling me to coordinate and giving me the prices.

[A]

No, no, wrong.

[B]

It's here. I'm responsible for my half. We've been dating four and a half months, so I won't really know anyone at the wedding. Seems like it could be fun. But now I'm really mad at him. I'm only going if he pays for me. Do I tell him this or do I just break up? What do I do?

[A]

Yeah, you Just tell him that. Or just. Yeah, maybe. She must really like the guy. No. Break up if it's even in the plan. He was vetting you out to make.

[B]

Sure you were cool enough to even invite.

[A]

Probably, but just be like, I can't afford to go, but I'd love to.

[B]

So if you want to help me.

[A]

Out, that'd be great. Yeah. I don't know. Do any of us think that he should be making her pay at all? No, he invited her. Yes, exactly. However, if he pays, she better be putting out. That is a contract, okay? Yeah. It's a legal, binding contract. And when you're telling her about it, you need to hit your hands when you're telling her stuff. Yeah. Why would this guy. This is a contract. Yeah. No. Destination weddings are awful anyway. Infuriating. It could have been fun for a new couple to go to the Bahamas, though.

[B]

Yeah.

[A]

Have some drinks.

[B]

Yeah.

[A]

Meet some of his friends. But he ruined it. Yeah.

[B]

Yeah. His only save would be if he's like, oh, I was just showing you, and I was gonna reimburse you all of the money, but I didn't, you know.

[A]

No, no. Right. Even that's. Yeah. You know, he wants her to pay. Clearly. Yeah. Oh, yeah, yeah, yeah. But he's. I just don't think that's proper. He's cheap as the day is long. Okay. Should have phrased it differently, screaming from him. What do you got, Allie?

[B]

Dear Allie, one of my best friends got pregnant and she won't reveal who the father is. It's causing some problems in our friend group because some people are thinking the reason she won't tell us is that it might be one of her husbands. Wow.

[A]

I don't know what. I think this is on Netflix again. I hope this is on Netflix. I want to watch. I want to hear. I want to make sure I heard this correct. The friend is pregnant, won't say who the father is. The other ladies think it could be one of their husbands. Yes.

[B]

And that's why she won't tell. This is awesome. Then she goes on to say, I thought I said maybe. She went to a clinic. And they said she would have told us about it if she was gonna take that route. So something weird is going on. What do you guys think?

[A]

I think women should not be allowed in groups anymore. You're not feed into your San anything more than two. And it has to be reviewed. Yes. By a judge. And be okay. Because when you get together, somebody. This may be all hell breaks. This may be happening because of all those Shows like this.

[B]

Yeah, Literally. Yeah. She made it. I just love that they're all side eyeing each other's husbands.

[A]

Well, look, we all know how awful men are and this could happen. Absolutely. No, but all. He's right. She. She may not. Yeah, she could have had back to back nights and I don't know what it was. So how can I tell you? Aren't there cases where a woman had twins and one's from one guy and one. Oh, yeah. That's amazing. Yeah, that's crazy. That's a girl having a good time is what that is. Oh, they've had twins that are black and white. Oh, I love that. Wow. Yeah. Like the cookie. Ebony at Ivory in the maternity ward. Look to the cookie. Wow. Well, that's interesting. I. What do you think, Ali? Yeah. You're so smart.

[B]

What do I think?

[A]

Yeah.

[B]

Yeah. I think Jess is right. I think she probably doesn't know. She doesn't want to say, hey, I've been with a bunch of guys who are potentially the dad. But wouldn't you think she would tell someone who's potentially the dad? Isn't it going to come out that way?

[A]

But yeah, I think. I don't blame her for not telling these loony chicks. I think there should be a big reveal. Like they bring a cake and they cut it like a gender party, except it'll be who the dad is.

[B]

That would be a good Netflix show.

[A]

Look, Susie, it's your husband.

[B]

All the husbands.

[A]

The thing that I find amazing is that they still call her a friend if they think she's screwing their husbands. Right. But you know what's gonna happen? Whoever's husband it is, the remaining ones are gonna talk about her. And that's why they're all excited about it. It's none of their husbands. Please. They're all bat crap.

[B]

No. After this baby comes out, we know what it looks like.

[A]

If it has red hair. Crazy Fred. They just can't stand the fact that she's keeping something to herself. Yeah. I hate, I hate. We have to know. I think it'd be really fun. My reveal party. Now I think about this. All the husbands are there. Which ones? Which one's getting the most strong? One guy sweating and smoking. I don't know. It could be me. Yeah. Jerry Springer type DNA test reveal. She got hit by lightning. Oh, my gosh. That's a great idea, Tom. Each one of these friends can go.

[B]

Home to their husbands and say, well.

[A]

We found out who the dad is. And just see their reaction. Yeah.

[B]

Try it. Yeah.

[A]

It's just. It's turned into a war zone. I want to know. Holy hell.

[B]

Or after the child's born, each person can pull a hair and get the test done themselves.

[A]

Yeah, there's that. Okay, let's move on. Ali Green is our guest. The show is Sexy Time. We've really done a lot of good work today.

[B]

Oh, we're killing it. Dear Allie. Okay, this is a. We have to interpret this because I had a friend with. I had a friends with benefit situation who was really into Beaches, because I don't know what you can say on air. Do you know what I'm talking about?

[A]

Beaches. Is this from a man or a woman?

[B]

It's a woman.

[A]

So she likes three ways. Is that right? What? Beaches, bitches. She wants to do with Bette Midler and Barbara Hershey.

[B]

Beaches.

[A]

No, no, no, no. You mean blowies. Blowies.

[B]

There we go. Should I replace it with that? I had a crush on him, so I would do that for him sometimes. But since then, I've gotten into a relationship that's now ended, but my crush on him also ended as well.

[A]

Okay.

[B]

He wants to resume our situation, and since I'm not that into it, I said, what do I get out of this?

[A]

There you go.

[B]

So he said, well, where do you want to go to dinner? I'll take you out. I picked a place. We went. I gave him his beach. We kept on doing that tit for tat for a while. Like, I need new sunglasses. Beach, I want a shirt. 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. And now we're fighting as if we're in an actual relationship.

[A]

I know what the problem is.

[B]

I told him he's acting like I'm less than human.

[A]

No, he's stupid. He's very, very stupid. First of all, you've gone pro, right? Let's be honest here.

[B]

Yeah, pretty much.

[A]

You've gone pro, and it's only a matter of time before you're just doing it for cash. And just Venmo me. This is. This is where I wish it was the, like, the Ann Landers thing, that she'd write back, you know, dear whore, Dear whore. And Walla Walla. How does she finish the letter?

[B]

Just bottom line. She said, we're actually in a fight, and I'm telling him we're not going to do it anymore. He wants to continue, but I have to admit, this is all turning me on now. And I'd miss the dinners and free stuff. Should I just keep doing it?

[A]

Maybe just up. I'll be Alsman. You're up the ante. Charge more double.

[B]

Yeah, yeah. Girlfriend, I need more Birkin bag.

[A]

Wait a second. It's not insane. You. You could just keep going until you price yourself out, but wait a second, wait a second. If you're keeping a. We're missing the whole thing. I can't believe you never thought about this. Are you familiar with blackmail? Oh, yeah. Yeah. Start keeping some really solid records here, and then down the road. You want your girlfriend to find out? Yeah. What's an expensive purse, Christy? Oh, well, Birkin is.

[B]

What? You.

[A]

A Birkin? That's a thing? Okay. They like the shoes. Birkenstock? No, much nicer. Okay. It's an Hermes bag. Yeah. Okay, well, Hermes. Okay.

[B]

Yeah, that's it. Keep up in the onions. Too expensive, I guess.

[A]

Not Hermes. No. Okay, I think we can squeeze in one more letter. I'm enjoying this so much. Ally. What do you got here?

[B]

Ally? I have a really hot girlfriend. And for the most part, we get along great. But when we fight, she goes really for the jugular. She starts saying, look at me and look at you, and basically telling me I should be grateful to be with her.

[A]

Oh, my God. Let me tell you something. I've been there. Get out. Get out. Now. That's the way she actually thinks. You just have to weather the storm, sir. Get out.

[B]

Tom. Nailed it. Because she's probably right to a degree, but it makes me wonder what she's thinking of me when we're not fighting. Last time we fought, I said, fine, go find someone better. If that's the case. And she told me she's just too lazy. So mean. Right?

[A]

Would you guys stay or leave? That's like being settled for. What a. What a combo. Yeah. Mean and lazy. But she's hot. Apparently she's a nine or something. So hot. So, so hot. So hot. Get some beaches first, I think. Yeah, you deserve better. It sounds to me like. Yeah, you deserve better. Man. Don't put up with that.

[B]

Yeah.

[A]

How much do you settle for just because she's good looking? Oh, man. I have a ex wife I pay money to just for that reason. Horrible person. But she was hot. Well, thank you. Nice job, Ally. Always a great pleasure.

[B]

Thanks, guys.

[A]

Yes, thank you, Allie. Don't get too sunburned. Okay. See ya.

[B]

Bye, Ally.

[A]

Boy, we did good work today.

[B]

Those are interesting.

[A]

Is that a bathing suit you're wearing? Can you. Can you mail it to me? That's it for another Bob and Tom show. Extra. Catch us on itunes, Google Play and Stitcher for Bob and Tom. Extra. This is Christopher. Take care, everybody. And Doug. Here we have the Limu Emu in its natural habitat, helping people customize their car insurance and save hundreds with Liberty Mutual. Fascinating. It's accompanied by his natural ally, Doug. Limu. Is that guy with the binoculars watching you? Us. Cut the camera. They see us. Only pay for what you [e-mail] Liberty. Liberty. Liberty. Liberty Savings Fairy. Underwritten by Liberty Mutual Insurance Company Affiliates. Excludes Massachusetts.