32: Vault: She Wants a Temporary Winter Romance

Summary

The Bert Show Podcast – Episode 32: Vault: She Wants a Temporary Winter Romance

Date: May 18, 2026

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Episode Overview

This episode of The Bert Show dives into the idea of a “winter boyfriend” — a seasonal romance that lasts only during the colder months. In a lighthearted, humorous, and candid conversation, the hosts and callers explore the pros, cons, and logistics of having a boyfriend specifically for winter, echoing both current dating trends and clever social experiments. The conversation touches on gender roles, emotional attachments, social expectations around holidays, and whether men or women would be better at keeping things casual.

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Key Discussion Points & Insights

1. Concept of a “Winter Boyfriend”

• The main theme centers on the intentional, temporary nature of a winter romance — from November to February or March.
• Purpose: “A winter boyfriend is a boyfriend that you have and you just stay in... someone to watch movies with, someone to cuddle with, someone to go walk and hold hands in the mall with. Nothing that lasts...just those couple of months.” – Co-host 1 (02:06)
• The idea is compared to rotating a wardrobe: just as you have seasonal clothes, you could have seasonal relationships.

2. Setting “Contractual” Boundaries

• The group discusses honesty up front, suggesting a relationship “contract.”
• Quote: “You would let him know immediately in the beginning of the season. Like, I just want to let you know that this is over [on] February 26th or whatever.” – Host (02:32)
• Discussion about a possible year-round strategy: winter boyfriend, single in summer, keeping options open in spring and fall (02:54–03:14).
• Noted that the bar for impressing each other is lower in this context; no need for extravagant behavior or presents.

3. Social & Practical Advantages

• Having a plus-one for holiday events, guaranteed New Year’s Eve kiss, and Valentine’s Day present.
• Avoiding the social “drama” of being single during the holidays.
• Quote: “You always have a date. You have a New Year’s kiss and a Valentine’s Day present. So it’s all wrapped up in this nice little bow. And we thought it was an amazing idea.” – Co-host 1 (03:27)

4. Gender Dynamics & Emotional Investment

• The hosts speculate on whether guys would sign up for such an arrangement. Consensus: many men would be interested due to its clarity and casualness (05:30–05:48).
• Debate: Would women be able to maintain emotional boundaries more than men?
  • Host: “I don’t know women are capable of doing this...once you start to get invested...y'all get so emotionally attached. Where guys could.” (08:04)
  • Co-host 3 (defiant): “Now he’s saying, we can’t do it. We gotta do it.” (08:19)
  • Co-host 2: “There’s no way women can’t do it. No way.” (08:21)

5. Logistics: Gifts, Breakup Timing, & Clauses

• Major concern: gift-giving expectations (Christmas, Valentine’s Day).
  • Suggestion: “We only do cards for Christmas.” (07:28)
  • Pushback: “No, I don’t think I’d be okay with a card...It’s gotta be something a little more.” – Co-host 3 (07:37)
• Practical suggestion: set expectations up front in the “contract.”

6. Caller Insights & Real-Life Examples

• A caller references John Mayer’s song “St. Patrick’s Day” as a musical parallel to this concept (05:05–05:23).
• Another male caller claims to do this every winter, breaking up after Valentine's Day. Says women are often interested for the same reasons (09:18–10:01).
  • Quote: “[With] women...a lot of women out there really, really like the idea because during the summertime you can hit the gym, look good for the beach and stuff.” – Caller 1 (09:47)
• Discussion about physical intimacy: not always a given, but often part of the arrangement (09:06–09:15).

7. Can It Work? Potential Pitfalls & Final Thoughts

• Hosts discuss the risk of catching real feelings; emotional detachment is seen as the biggest challenge for women.
• Suggestion: it might work best with someone you’re attracted to but don’t actually like deeply (08:33–08:43).
• Final comments surface doubts: some skepticism about whether anyone (men or women) can keep things so cleanly compartmentalized.

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Memorable Quotes & Timestamps

• On running out of things to talk about:
  “Well, when they ran out of stuff to talk about, they talked about running out of stuff to talk about.” – Host (01:36)
• Defining the arrangement:
  “You want someone to snuggle with, it’s cold outside...You want to just stay in and watch a movie.” – Co-host 1 (03:47)
• Male perspective on the arrangement:
  “If I’m a single guy...and you said, ‘let’s just do this for the next four months and it’s over the day before St. Patrick’s Day,’ when I was single, I’d have signed up for that immediately.” – Host (05:33)
• On gifts:
  “Is there like going to be an agreement? Like, okay, this is just to keep each other warm. No gifts, no presents. We’re having to do the family thing, then maybe that would work.” – Caller 2 (07:19)
• On emotional boundaries:
  “Your idea sounds great on paper, but I think once you start to get invested...come February, y’all get so emotionally attached.” – Host (08:04)
• Can women keep it casual?:
  “Now he’s saying, we can’t do it. We gotta do it.” – Co-host 3 (08:19)

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Notable Segments with Timestamps

• Exploring the “Winter Boyfriend” Concept: 01:54 – 03:14
• Seasonal Dating Contracts and Rules: 02:32 – 04:12
• Gifts and Contractual Clauses: 04:41 – 05:41, 07:13 – 07:39
• Gender Debate and Emotional Attachment: 08:04 – 08:30
• Caller Testimonies and Real-World Examples: 05:05 – 05:23; 09:06 – 10:16

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Tone and Style

The show’s tone is witty, playful, and slightly irreverent. The co-hosts spar and tease, but there’s genuine curiosity about modern relationship dynamics and acknowledgment that real-life boundaries are fuzzy and feelings unpredictable.

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TL;DR Summary

In this episode, The Bert Show crew and callers consider whether a “winter boyfriend” arrangement—a romance that lasts only for the colder months—could really work in practice. While the idea is appealing for its simplicity and seasonal comfort, the group wrestles with issues like expectations around gifts, communication of boundaries, and the ever-present risk that someone will catch deeper feelings. Listeners chime in with their own experiences and musical references, leaving the episode as both a thoughtful and thoroughly entertaining take on love in the “cuffing season.”

Transcript

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[Host (possibly Wendy)]

The Birch Show So I was chatting

[Co-host 1]

with a girlfriend of mine the other day and you know, you kind of get bored of chatting. I mean, you just have nothing to talk about. But we thought this was a good idea.

[Caller 1]

What?

[Co-host 2]

Girls run out of things to talk about. When does it happen?

[Co-host 3]

Sometimes you might come up with new things.

[Co-host 1]

You come up with different things to talk about.

[Host (possibly Wendy)]

I heard, I saw this on the Atlanta two day walk for breast cancer.

[Co-host 2]

They ran out of stuff to talk about.

[Host (possibly Wendy)]

Well, when they ran out of stuff to talk about, they talked about running out of stuff to talk about.

[Co-host 1]

Right?

[Caller 1]

Okay.

[Host (possibly Wendy)]

They're like, can you believe we ran out of stuff to talk about? That's weird because I never run out of stuff to talk about. Do you? When's the last time you ran out of stuff to talk about? And they talked about that for 10

[Co-host 3]

minutes and then came up with more

[Co-host 2]

talk something else to talk about during that conversation. Thought of something else.

[Co-host 3]

Right.

[Co-host 1]

We thought of a brilliant idea and didn't know if anybody else has Done it. And it could be a trend. But we want winter boyfriends. And this is the idea behind having winter boyfriends.

[Co-host 2]

Winter or winter?

[Co-host 1]

Winter.

[Co-host 2]

Okay.

[Co-host 1]

Winter boyfriend. Like, seasoned boyfriends that you only have from the period, like, of November through, let's say, March, because that's when it's really cold outside. You don't really want to go out too much because then you got to bundle up. You don't want to wear the short dresses or the jackets. But a winter boyfriend is a boyfriend that you have and you just stay in somebody to watch movies with, someone to cuddle with, someone to go walk and hold hands in the mall with. Nothing that lasts in, but in these couple of months.

[Host (possibly Wendy)]

So you would let him know immediately in the beginning of the season. Like, I just want to let you know that this is over. February 26th or whatever.

[Co-host 1]

February 29th, it's going to be over. Because then you got to get back in the gym. Then you don't have time for him. You got to get back in the gym to look good for summer.

[Host (possibly Wendy)]

Okay, so it's a contract you make, and you let him know. Can this translate to, like, the same way that we trade out wardrobes? Can you have a boyfriend for, like,

[Co-host 2]

cleaning out your closet?

[Host (possibly Wendy)]

Spring, summer, and winter? You got four boyfriends a year or two.

[Co-host 1]

Well, summer you should be single. So that's the no boyfriend zone.

[Co-host 3]

Spring is like, you know, everybody's got spring fever. So you don't want to, like, limit your options in the spring.

[Co-host 1]

And then fall, you have your Halloween costumes, and you want to go be single for that because you don't want a boyfriend tagged along with you because you want to wear the short outfit. And boyfriends don't let you do that.

[Co-host 3]

Right?

[Host (possibly Wendy)]

Yeah.

[Co-host 3]

Football season is also in the fall. Winter really is the best time to have a boyfriend.

[Co-host 2]

Yeah, duh, birds.

[Co-host 1]

It's the perfect time to have a boyfriend.

[Host (possibly Wendy)]

It is making kind of sense to me here.

[Co-host 3]

Yeah.

[Host (possibly Wendy)]

Because then you have a boyfriend for the holiday parties and Christmas parties and all that stuff.

[Co-host 1]

You always have a date. You could potentially, you have a New Year's kiss and a Valentine's Day present. So it's all wrapped up in this nice little bow. And we thought it was an amazing idea, and now we want one.

[Co-host 3]

I like that.

[Host (possibly Wendy)]

I think it actually has some legs.

[Co-host 2]

Wendy, do you really want a winter boyfriend, or will you just settle for any guy who will call you back more than twice?

[Co-host 3]

No, just a winter boyfriend.

[Co-host 1]

Your boyfriend.

[Co-host 3]

I like that idea.

[Co-host 1]

You want someone to snuggle with it's cold outside. You want to light a fire. You want to just stay in and watch a movie. It's gross going outside, and it's going to get nasty out eventually. In Atlanta.

[Co-host 3]

It's so true. Cause think about it. In the summertime, like, it's no fun to snuggle with anybody. Cause you're like, ah, get your hot, sweaty body away from me.

[Caller 1]

God.

[Co-host 3]

Like, ew, you're taking up too much room. But then in the wintertime, like, you do want to have somebody to, like, snuggle with and spoon and, you know, somebody to warm up your feet.

[Host (possibly Wendy)]

So you'd immediately make the agreement with them. It's like, I just want to let you know, this is over in November, but we're both going to be with each other.

[Co-host 3]

It's February. February, yeah.

[Co-host 1]

Starts in November, ends in February. But I don't know if it works or if it could work.

[Host (possibly Wendy)]

I don't know if I'm a guy and I had a woman approach me, and I. I knew that was four months of having a girlfriend, then she was gone in February, I'd sign up immediately.

[Co-host 2]

You would have a challenge, though, like, at Christmas, like, how much do you spend on a temporary relationship?

[Host (possibly Wendy)]

That's true.

[Co-host 3]

I mean, even just a small, little, thoughtful gift would be okay.

[Co-host 1]

A card.

[Host (possibly Wendy)]

Because the entire relationship, the bar is set a little bit lower. You know, it's temporary. And you're just here because it's winter, and I'm just here because it's winter. So you don't really have to impress.

[Co-host 3]

Yeah, right.

[Co-host 1]

I mean, you're in your sweatpants. He can be in his sweatpants. You don't need to get all done up. You're just automatic boyfriend, girlfriend.

[Host (possibly Wendy)]

There's just brilliance in your simplicity. Sometimes it really is.

[Co-host 1]

That's what I do.

[Host (possibly Wendy)]

Hey, Lori. Good Morning. You're on Q100.

[Caller 2]

Hey. I just wanted to tell Wendy that there is a John Mayer song about this very topic.

[Co-host 3]

No.

[Caller 2]

Yep. It's on the Room for Squares album. It's like, the last track.

[Co-host 2]

And what's it called?

[Caller 2]

It's called St. Patrick's Day. We'll be all right till St. Patrick's Day.

[Host (possibly Wendy)]

Okay.

[Caller 2]

It's good.

[Co-host 1]

So we're moving it to St. Patrick's Day, because then you can go out.

[Co-host 2]

Yeah. And you get hammered and find somebody

[Host (possibly Wendy)]

new on your own.

[Co-host 1]

That's perfect.

[Co-host 3]

I wonder if a guy would really sign up for that.

[Host (possibly Wendy)]

If I'm a single guy and a woman approached me that I was attracted to, you know, you'd Have a week to really get to know each other. And then said, let's just do this for the next four months and it's over. The day before St Patrick's Day when I was single, I'd have signed up for that immediately.

[Co-host 3]

Really?

[Host (possibly Wendy)]

Yes.

[Caller 2]

Well, see. What?

[Host (possibly Wendy)]

Well, a sure thing with a hottie until February.

[Co-host 3]

Yeah. But I feel like there's like a benefit to the girl, but maybe not as much to the guy because he's given up his single status to sort of be a foot warmer.

[Co-host 2]

He doesn't care.

[Host (possibly Wendy)]

He doesn't care so long as you. It's about consistency through those months. And if you know you got a hottie that you're attracted to, consistent. You could be consistent for four months and then it's over. I would sign up for that and

[Co-host 2]

I'd be inclined to say that, I'm with you, Wendy.

[Co-host 3]

Let's find him.

[Co-host 2]

It would make the guy more into you because like, the guy, the guy's like, if March rolled around and St Patrick's Day was coming up and you said to him, God, it's gonna be such a bummer three weeks from now we're not gonna be together, he'd be

[Host (possibly Wendy)]

like, more attentive because he knows he's on a lot.

[Co-host 1]

Wendy, I thought of the brilliant idea. I need to market this. I need a website.

[Host (possibly Wendy)]

Hey, Jessica, good Morning. You're on Q100.

[Caller 2]

Hi. I have a 25 year old brother. I'm sorry, Wendy, but he is right now trying to think of ways to break up with his girlfriend so he doesn't have to do the hol. Like he doesn't want to do the gifts for Christmas. He doesn't want it. And Valentine's Day comes around, so. I know. And a lot of his friends are the same way. Like they don't want girlfriends because they don't want to have to pay and buy the gifts during that season.

[Host (possibly Wendy)]

But here's the difference. Your brother is invested in a real relationship, so he has to impress. If you have a girlfriend for just four months, the bar is set so much lower for the both of y'.

[Co-host 3]

All.

[Host (possibly Wendy)]

The pressure is off. It's just a little something here and a little something there.

[Co-host 1]

You could put a clause in, like a contract.

[Caller 2]

Is there like going to be an agreement? Like, okay, this is just to keep each other warm. No gifts, no presents. We're having to do the family thing, then maybe that would work.

[Co-host 3]

Yeah.

[Co-host 1]

Put a clause in your contract, your four month contract of being together. Your clause is we only do cards for Christmas.

[Caller 2]

That might work, actually.

[Host (possibly Wendy)]

I'm telling you.

[Co-host 3]

No, I don't think I'd be okay with a card.

[Host (possibly Wendy)]

If you just want something a little bit more. Something?

[Co-host 3]

Yeah, it's gotta be something a little bit more. Especially if he makes good money and, you know, it's not like tapping him dry to get you a gift. He's got to get something.

[Host (possibly Wendy)]

It just has to be something sentimental enough to where you feel more than just you want to feel more than the winter girlfriend. But you still are the winter girlfriend.

[Co-host 3]

Yeah, like some really pretty earrings. Right. That would go nice with a winter sweater.

[Host (possibly Wendy)]

See, here's where. I don't know women are capable of doing this. Actually, like, your idea sounds great on paper, but I think once you start to get invested and he's coming over all the time and you're doing the snuggling thing, come February, y' all get so emotionally attached. Where guys could.

[Co-host 3]

We can end it now. It's a challenge.

[Host (possibly Wendy)]

Women can't do it.

[Co-host 3]

Now he's saying, we can't do it. We gotta do it.

[Co-host 2]

There's no way women can't do it. No way.

[Host (possibly Wendy)]

You can't have it.

[Co-host 2]

Especially the two women in this room. No way.

[Caller 2]

No.

[Co-host 2]

Not possible.

[Co-host 3]

What if it was somebody that you were attracted to. But you just didn't really like them all that much?

[Host (possibly Wendy)]

That might work, because then could you turn it on and turn it off?

[Co-host 3]

Like, if you were just physically attracted to them. But you didn't really like their lifestyle or what they did for a living or whatever. Like, you didn't really like them as a person. You just were attracted to them, then it could work. Because then you would just be getting, you know, one part fulfilled and then.

[Co-host 1]

But the emotional part is. So it's easier again.

[Co-host 3]

Kick it to the curb.

[Host (possibly Wendy)]

Good morning, Brett. You're on Q100.

[Caller 1]

Yeah, I just wanted to ask Wendy. What is the possibility or the chance of sex in this temporary boyfriend deal? Because otherwise, you're not gonna get any gut.

[Host (possibly Wendy)]

That's not a given deal. Hey, Chris.

[Caller 1]

Hey. How's it going?

[Host (possibly Wendy)]

Okay. How are you?

[Caller 1]

I'm doing good. You know, that's actually a good idea. I do it every winter, and we break up after Valentine's Day.

[Host (possibly Wendy)]

So when do you guys get together? What day is that?

[Caller 1]

We normally get together sometime in November because, you know, it's starting a cold month. And then you need somebody for Thanksgiving and then Christmas and New Year's.

[Co-host 1]

Is this a steady girl? So is it the same girl every year?

[Caller 1]

No, it's a different one. Just whoever I come across and I decide to date.

[Co-host 3]

And does she know that from the beginning?

[Caller 1]

Yes. They, you know, women are pretty much up for the same thing that men are when it comes to the wintertime. A lot of women out there really, really like the idea because during the summertime you can hit the gym, look good for the beach and stuff.

[Co-host 2]

Is there any chance you're good looking but stupid?

[Caller 1]

What's that?

[Co-host 2]

Because Jen's looking for a good looking stupid guy.

[Caller 1]

Well, you know. Yeah, there's plenty of us out there. All men are stup.

[Host (possibly Wendy)]

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