30: Vault: Which Guy Should She Hook Up With for the Holidays?.

Summary

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The Bert Show – Episode 30: Vault: Which Guy Should She Hook Up With for the Holidays?

Date: May 18, 2026
Hosts: Bert Show Cast (Melissa, Jen, Wendy, et al.)
Main Theme:
This episode dives into the light-hearted, candid world of “hometown hookups”—those flirtatious, sometimes steamy reunions with familiar faces when heading home for the holidays. The hosts chat with listeners about the options and “rules” of these encounters, exploring old flames, new potential, and even long-standing traditions. Humor, playful banter, and a touch of female empowerment fuel the conversation.

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Key Discussion Points and Insights

1. Defining the “Hometown Hookup” (01:31 – 02:26)

• Jen opens the floor with: “One call for hometown hookup, one voice. Disguised or no voice.” (01:31)
• The crew defines “hometown hookup” as a recurring, near-guaranteed romantic (or physical) reconnection when visiting your hometown.
• Jen: “The hometown hookup is somebody that you always hook up with when you go back home. It's like a sure thing…you know what's going on, and you just show up. You guys…spend two hours in a bar, and then you go do it.” (02:14)

2. Amber’s Dilemma – Three Potential Guys (02:00 – 07:33)

The Candidates:

• Brother’s Friend: Older, never hooked up with him but always had a crush. He’s picking her up at the airport with a possible hour alone before her brother’s arrival. (02:14 – 03:39)
  • Amber: “He's my brother's friend, but I've always had a crush on him, and he's picking up my brother, but my brother's flight gets in an hour after mine, so I'm gonna have, like, an hour to hang out with him at the airport.” (03:16)
• High School Friend/Prom Date: A familiar face she’s always wondered about—“the one that got away.” They have plans for breakfast before the family meal. (04:07 – 04:38)
  • Amber: “We have plans tomorrow for breakfast…I actually want to see if more can happen” (04:38)
• Old Acquaintance from High School Group: Not close friends but always found him attractive; interested to see “how he’s been looking.” (05:20 – 05:39)

Strategy & Mindset:

• The hosts joke about “playing the odds” and approach the process with a numbers game mentality.

  • Melissa: “I think it's smart playing the odds.” (04:46)
  • Jen: “It's a numbers game here.” (04:48)

• Playful debate about how women vs. men talk about hookups.

  • Wendy: “That's what's wrong with women is they just throw it out there to every available guy…” (04:49)
  • Melissa: “Women don't talk about it like that. We'll be like, yeah, we're gonna see if there's a romance that sparked with somebody and maybe have a make out. We don't say the S E X word.” (05:51, 06:08)

Intentions and Hopes:

• Amber is clear she’ll “definitely need to” get physical with someone:
  • "I really do. Plan. Yes, I definitely need to.” (06:05)
• When asked which guy she hopes works out:
  • “Really? The guy I went to the senior prom with over breakfast.” (06:35)

Limits and Playful Prodding:

• Hosts prod about the possibility of her hooking up with all three.
  • Jen: “Is there any chance...you end up...with all three of them?” (06:39)
  • Amber: Firmly says, “No.” (06:55)
  • Jokes abound about “giving thanks” for Thanksgiving weekend. (07:15, 07:24)

3. Listener Call: A 13-Year Thanksgiving Tradition (07:55 – 10:48)

• Caller Hayley shares her annual ritual: always hooking up with her ex-husband when she goes home.
  • “When I go home, I always hook up with my ex-husband…one thing always went right, and I make sure I get it every year.” (08:02)
• No embarrassment, describes it as a “Thanksgiving tradition.” Neither have remarried—unsaid but understood arrangement.
  • Amber (caller): “…even if he gets married, I'm getting mine.” (08:34)
• The relationship was amicable post-marriage; the physical chemistry “always worked."
  • Amber (caller): “A part of me will always love him and always love parts of his anatomy.” (09:31)
• Asked about logistics: happens for 13 years, location varies, never rekindled romance.
  • Jen: “I'm sure during the 13 years, you've been seeing guys…and he’s been seeing women…and then…he just puts them aside for a couple hours.” (10:10)
  • Amber (caller): “Yeah. It's sex. It's not anything else. It's just like remembering the good times.” (10:19)

4. Playful Banter & Notable Quotes

• The cast riffs on euphemisms for sex, especially around holiday terms:
  • Melissa: “Women appreciate feasting. Giving thanks.” (07:24)
  • Jen: “…let's find out how much thanks you gave over the weekend.” (07:32)
  • Wendy: “Her motor is stuff that turkey. It's okay for her to say, stuff that turkey.” (07:38)
  • Jen: “Mash those potatoes. Cream and spinach.” (07:49)
• Gently mocks differing attitudes towards casual connections between men and women, with warmth and tongue-in-cheek humor.

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Memorable Moments & Quotes

• Amber (about her intentions): “I really do. Plan. Yes, I definitely need to.” (06:05)
• Jen (on the ‘numbers’ game): “It's a numbers game here.” (04:48)
• Amber (annual hookup): “When I go home, I always hook up with my ex-husband. There's a lot of things that didn't go right, but one thing always went right, and I make sure I get it every year.” (08:02)
• Amber (annual hookup, tradition): “…even if he gets married, I'm getting mine.” (08:34)
• Hosts swapping euphemisms: “Mash those potatoes. Cream and spinach.” (07:49)
• Melissa (on the Thanksgiving theme): “She was giving thanks.” (07:15)

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Timestamps for Key Segments

• Defining hometown hookup: 01:31 – 02:26
• Amber’s three candidates: 02:00 – 07:33
  • First guy: 02:14 – 03:39
  • Second guy: 04:07 – 04:38
  • Third guy: 05:20 – 05:39
• Discussion on intentions and language: 05:47 – 06:35
• Listener Hayley’s tradition: 07:55 – 10:48
• Holiday euphemisms riff: 07:15 – 07:53

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Tone & Vibe

• Lively, teasing, unfiltered, and empowering—celebrating women owning their choices in the dating/hookup landscape, with the hosts supporting each other and listeners with humor and realness.
• The episode avoids judgment, leans into holiday metaphors, and fosters an upbeat environment for discussions often shrouded in taboo.

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For anyone who missed the episode:
This installment is a cheeky, joyful look at modern hookup culture, nostalgia, and the reassuring comfort of annual “traditions.” Whether you’re navigating love, lust, or laughter this holiday season, The Bert Show wants you to know: you’re not alone in playing the odds, reminiscing, or just giving a little thanks.

Transcript

[Narrator/Advertiser]

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[Melissa]

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[Wendy]

The Birch Show.

[Jen]

One call for hometown hookup, one voice. Disguised or no voice.

[Wendy]

Disguise and fake name.

[Melissa]

Okay.

[Wendy]

Which I think Wendy designated as Amber because she said that sounded whorish.

[Melissa]

I'm not whorish.

[Jen]

This is not whorish. This doesn't even count. Like Jen said, this doesn't even count towards your number. It's somebody that you've hooked up with before.

[Melissa]

So it's cycling.

[Jen]

Yeah. The count stays the same. And this is good.

[Melissa]

It's good for yourself. It's good for the environment. They should get some once a year.

[Jen]

Hey, Amber.

[Amber]

Hey.

[Jen]

How are you?

[Amber]

Good. How you guys doing?

[Wendy]

Good.

[Jen]

You got a sure thing lined up when you go home this weekend?

[Amber]

Well, I don't know about shirt. I have three possibilities, so I'm really excited. I don't know which one. Maybe. I don't know.

[Jen]

Let's clearly define what hometown hookup is before you talk about potentially who you're hooking up with this weekend. The hometown hookup is somebody that you always hook up with when you go back home. It's like a sure thing.

[Amber]

You.

[Jen]

He knows what's going on, you know what's going on, and you just show up. You guys, you know, spend two hours in a bar, and then you go do it.

[Narrator/Advertiser]

Mm.

[Amber]

Well, none of them are sure things, but I broke up with my boyfriend that I was with for, like, two years about six weeks ago.

[Melissa]

Okay.

[Amber]

And I don't. I don't know, ever. We're all friends, the same people, and I just feel like I need fresh territory, you know what I mean? Because my ex boyfriend knows everybody I know down here, so I've some of the guys, like the three, I don't know. One of them, well, is my brother's friend, and I've never hooked up with him, but I've always thought he was really hot and had, like, a secret crush on him. And he's supposed to pick me up today at the airport.

[Melissa]

Oh, that's cool.

[Narrator/Advertiser]

Okay.

[Melissa]

Good potential. But you've never been there before, though, so that's not a sure thing.

[Amber]

Because he's older, and, like, when we were kids, it's not that much older now, but when we're younger, it's a little older. It's my brother's friend, but I've always had a crush on him, and he's picking up my brother, but my brother's flight gets in an hour after mine, so I'm gonna have, like, an hour to hang out with him at the airport.

[Jen]

So this guy's gonna pick you up at the airport, and you've got an hour before your brother gets in just to, like, set the whole thing up for later in the weekend or hope.

[Amber]

I'm hoping. I mean, he doesn't know this is my plan, but he seems like I'm his best friend's little sister, so he's never approached me, but I can kind of tell. You know what I mean?

[Melissa]

So are you wearing something hot on the plane?

[Amber]

Yes. I have a really cute outfit on. I'm ready.

[Melissa]

So if they call it mile high club in the plane, what are in the airport?

[Jen]

Touchdown?

[Wendy]

You're going to have to ask that congressman who got in trouble for tapping his foot.

[Jen]

All right, so if he doesn't work out, then who's contestant number two?

[Amber]

Okay, this guy. I hooked up with him a little bit, you know, when we actually went to a senior prom together, but we were always just friends, and Just messed around a little bit. But I kind of feel like he's the one I let get away, you know, And I wish we weren't just friends in high school, so. But we are actually. We have plans tomorrow for breakfast before like the big family meal, you know, so he doesn't know. He thinks, oh, we're still great friends. But I actually want to see if more can happen, you know, depending on

[Melissa]

what happens with Big Brother on Thursday or on today, I guess.

[Amber]

So I want to like have as many chances as I can. I don't know which one is gonna. It's been. I don't know. I've been. I don't know.

[Melissa]

So I think it's smart playing the odds.

[Jen]

It's a numbers game here.

[Wendy]

You know what, that's what's wrong with women is they just throw it out there to every available guy and see which guy is interest. Guys aren't special to them. They're just pieces of meat.

[Jen]

I wish that trend happened 16 years ago. Too bad. It's really a hot trend now.

[Amber]

I'm not going to just throw it out, but I definitely have crushes on these guys. So I want to see which one is going to.

[Jen]

Have we even established what city we're talking about yet?

[Amber]

I'm going back to New York. That's where I'm from.

[Jen]

New York. Ok, and who is the third guy?

[Amber]

Well, on Friday night, a group of friends, we're going out and one of them is this guy. And again, I've always thought he was hot, but I've never done anything with him. And he's like, we were never close friends, but we've known each other since high school. And I just, I don't know, I want to see how he's been looking the past, you know, couple of years.

[Melissa]

Okay, awesome.

[Jen]

All right, so here's the one thing you do know that you're having sex in New York this weekend. You just don't know. Well, she is. You just don't know.

[Melissa]

Women don't talk about it like that.

[Jen]

You just don't know who it's going to be with. But it is happening.

[Melissa]

You don't realize women don't talk about it like that. We'll be like, yeah, we're gonna see if there's a romance that sparked with somebody and maybe have a make out. We don't say the S E X word.

[Jen]

So are you planning on getting physical for sure with one of these guys?

[Amber]

I really do. Plan. Yes, I definitely need to.

[Wendy]

We're speaking the same language.

[Jen]

What's wrong with the word sex?

[Melissa]

You just say it so harshly, like,

[Jen]

so she's having sex this weekend?

[Melissa]

No, we don't see that.

[Amber]

Having a moment.

[Melissa]

Be sweet, Megan.

[Wendy]

Of course she's gonna meet it. She's gonna meet a gentleman, and together they will make the beast. With two bags.

[Melissa]

No, that's gross. Amber, which one of these guys do you hope works out? I mean, which one do you want to work out the most?

[Amber]

Really? The guy I went to the senior prom with over breakfast.

[Melissa]

Okay, so breakfast.

[Jen]

Now, is it. Is there any chance at all that things go so well this weekend that you end up. How gently do I put this? With all three of them?

[Melissa]

Spending time with all three.

[Jen]

Spending time with all three of them.

[Wendy]

Having sex with.

[Amber]

No.

[Melissa]

You guys are such losers. We don't talk like that.

[Amber]

Yeah, I think we don't. I mean, I.

[Wendy]

Making love

[Melissa]

moments.

[Amber]

I just. I like them all. I'm attracted to all three of them. I'm not gonna, like, go, you know, I don't know. Anything could happen. But I wouldn't lose Thanksgiving.

[Jen]

So at the bare minimum, one. If you hit the lottery. Three for sure.

[Melissa]

Give thanks to all three of you. That's what we'll call this weekend. She was giving thanks.

[Narrator/Advertiser]

That's right.

[Melissa]

Appreciating again. Women appreciate feasting. Giving thanks.

[Jen]

All right, let's talk to you again on Monday morning, and let's find out how much thanks you gave over the weekend. Okay?

[Amber]

Okay. Happy Thanksgiving.

[Jen]

You, too.

[Narrator/Advertiser]

You, too.

[Melissa]

You give it to them. That's right. And wrap that turkey.

[Wendy]

Her motor is stuff that turkey. It's okay for her to say, stuff that turkey.

[Jen]

And those are okay because it's from a woman. But I can't say the word sex.

[Melissa]

I just gave Melissa the look. Like, dude, you're in the category with the boys.

[Wendy]

Mash those potatoes. Cream and spinach.

[Melissa]

Oh, that one's gnarly.

[Jen]

Hey, Hayley. Good morning. You're on the voice disguiser.

[Amber]

Good morning.

[Jen]

Good morning. How are you?

[Wendy]

Row that gravy boat?

[Amber]

When I go home, I always hook up with my ex husband. There's a lot of things that didn't go right, but one thing always went right, and I make sure I get it every year.

[Wendy]

What was it that went right? When you guys had sex.

[Amber]

Sex. That's all it is, sex.

[Jen]

She's not embarrassed about it.

[Melissa]

So you're like, every year. Every year you go back and you and your ex get together?

[Amber]

Yes.

[Melissa]

Now, are either of you remarried?

[Amber]

No.

[Jen]

Okay, so until one of you gets remarried, this Is the deal. And it's an unsaid deal.

[Amber]

Unsaid deal. And even if he gets married, I'm getting mine.

[Melissa]

Oh, you were there first. It's Thanksgiving tradition. You don't break tradition. No.

[Jen]

Have you guys agreed to that? That if one of you gets married, this deal is still on?

[Amber]

I don't think it's been agreed on, but out loud, in words, but I think it will continue.

[Jen]

So would it work the other way around if you got married? You would still go home and still.

[Amber]

Oh, hell yeah.

[Jen]

Oh.

[Melissa]

Oh, my God.

[Jen]

He's that good.

[Melissa]

Oh, hell, yeah.

[Amber]

Yep.

[Jen]

I'm curious.

[Amber]

How.

[Jen]

How bad was the relationship? And how long did it take you to actually break up with him knowing the sex was that good? Like, I would think that would keep you around longer than you really wanted to stay.

[Amber]

We partied friends, so we never had the I hate you kind of fighting relationship.

[Jen]

Okay.

[Amber]

So we parted friends and stuff. So we've always. I mean, a part of me will always love him and always love parts of his anatomy.

[Jen]

What. What city is this in that you're going to Seattle? And is there a. Is there a text exchange sometime this week, or does he just know you fly in the day before and you guys meet up on Saturday? He knows as a call.

[Amber]

We've been doing this for 13 years,

[Melissa]

and y' all didn't get back together.

[Amber]

Oh, no, we. We don't want that. So.

[Jen]

And I'm sure during the 13 years, you've been seeing guys at some point, and he's been seeing women, and then. So he just puts them aside for a couple hours.

[Amber]

Yeah. Yeah. It's sex. It's not anything else. It's just like remembering the good times.

[Jen]

And is it in the same place every time?

[Amber]

Oh, no.

[Melissa]

Be careful.

[Wendy]

Sometimes.

[Jen]

I meant hotel room.

[Wendy]

Sometimes, depending on how much wine they

[Melissa]

made to drink for 13 years, you can just mix it all up.

[Jen]

Yeah, I just meant hotel room. Thank you for calling, Hayden.

[Amber]

Thank you.

[Jen]

All right, have a good time this week and give. Thanks. Okay, Bye.

[Melissa]

Bye. No, she's been in the eggnog already. That's hilarious.

[Wendy]

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[Melissa]

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