Vault: She Wants To Celebrate Her Anniversary With Multiple Guys?!

Summary

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Podcast Summary: The Bert Show – “Vault: She Wants To Celebrate Her Anniversary With Multiple Guys?!”

Date: January 28, 2026
Podcast: The Bert Show (Pionaire Podcasting)
Episode Theme:
A listener, Lena, calls in to share her unconventional plan to mark the one-year anniversary of a breakup by organizing four dates in one weekend. The show dives into dating rebounds, confidence, and the modern world of dating — with humor, real talk, and anecdotes from the Bert Show cast.

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1. Episode Overview

The main theme of this episode is reclaiming personal happiness and confidence after heartbreak. Lena, having spent nearly a year moping after a three-year relationship, decides to “celebrate” the breakup anniversary by jumping back into dating — lining up four dates for one weekend. The Bert Show’s hosts dissect her plan, share insights about dating culture, and enthusiastically follow up to see how Lena’s dating “marathon” went.

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2. Key Discussion Points & Insights

Lena’s Background and Motivation

• Context: Lena broke up with her boyfriend of three years almost a year ago and has been struggling to move on, particularly around Valentine’s Day (00:09).
• Breakup Anniversary: Instead of mourning the milestone, she decided to take proactive steps to move forward:
  “Forget this. I’m not going to mope about this guy anymore. It’s over. I’m getting back out there and I have… four dates lined up for this weekend.” (00:22, Lena)

The “Four Date Marathon” Plan

• Intention: The hosts clarify that Lena intentionally scheduled four dates as a bold way to “bust the slump” and force herself into the dating pool (00:46-01:09).
• First Dates Since Breakup: These are Lena’s first real dates in almost a year.

The Hosts’ Take: The Slump Buster

• Hosts encourage Lena’s strategy:
  “If you’re gonna come out of this thing, come out of it strong man. Four days.” (01:04, Host A)
• Risk and Reward: They discuss the pros and cons, joking about the potential for rapid discouragement or success, given the intensity (01:14-01:36).

Date-by-Date Recap (02:09–06:12)

1. Thursday: The Group Coworker Date
   • Very casual, treated more as a group hangout than a real date.
   • “It was cool that it was like no pressure and we didn’t really hit it off, so it was fine. And so it was kind of like we can act like we didn’t even go on a date.” (02:47, Lena)
2. Friday: The Real Winner
   • Traditional dinner and drinks, lasting till after 3 a.m.
   • Good chemistry; ended with a kiss.
   • “I really like this guy. Like, this guy wins. He’s the only one I’m going out with again.” (04:45, Lena)
3. Saturday: The High School Throwback
   • Dinner and a movie, but feeling was awkward — no chemistry.
   • “It was just… the conversation was boring. I felt like I was kind of on an interview… no chemistry.” (05:00, Lena)
4. Sunday: The Canceled Date and a Callback
   • Lena, exhausted by Saturday’s bad date, cancels on the fourth guy and spends another day with “Friday Guy”, even seeing the same movie as Saturday.
   • “We spent all of Sunday together… I just kind of—I’m not gonna tell him [I saw the same movie].” (05:53, Lena)

The Hosts’ Commentary: Dating Strategy & Confidence

• Shorter Dates, More Check-Ins:
  Host A jokes about a universal “30-minute contract” in dating to save time if the spark isn’t there (03:22; 05:18).
• Concept of Safety and Support:
  The first group date is viewed as a wise “safety net” (04:22).
• Confession vs. Openness:
  Lena is not sure about telling “Friday Guy” how many dates she went on that weekend — the hosts affirm it could be off-putting if the number is too high (06:23).
• The Power of Confidence:
  The hosts agree Lena’s confidence, gained from knowing she had options, made her more attractive and successful:
  “It could have been the confidence that she brought, you know, with having four dates lined up… that confidence that made it so great with Friday Guy.” (07:09, Host E)
  “I had a whole bunch of dates lined up, and here it made me more confident because if Thursday didn’t work out, I had Friday lined up.” (07:53, Host A)

Societal Double Standard? (08:29–09:05)

• The hosts debate whether a man doing the same thing would be judged differently, with some agreeing the context matters (e.g. post-breakup, intentions).
• Humorous Boob Math:
  “That’s eight boobs. Boob math. It always comes down to boob math for us.” (09:05, Host A)

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3. Notable Quotes & Memorable Moments

• Lena, on her motivation:
  “Valentine’s Day was just, I guess when I hit bottom. And now I’m like, you know what? Forget this. I’m not going to mope about this guy anymore.” (00:22)
• On the Friday guy:
  “He’s the only one I’m going out with again.” (04:55)
• Host A, wishing for more honest early check-ins:
  “If we could just check in with each other on 30 minute increments on dates and each has the right to say, this is either going great or… you walk away with no social repercussion.” (03:31)
• On double standards:
  “Does it have the same texture? Or would you guys be all over him going, ah, stop being a whore. You have four women lined up in four days.” (08:29, Host A)

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4. Key Timestamps

• 00:09–00:22: Lena explains the breakup anniversary and her plan for four dates.
• 01:04–01:36: Hosts analyze the potential outcomes of Lena’s approach.
• 02:09–03:15: Lena details her first group “coworker” date.
• 04:28–05:18: Recap of Friday (the standout date) and Saturday (the flop).
• 05:53–06:23: The Sunday “date swap” and concerns about revealing too much to Friday Guy.
• 07:09–07:53: The hosts discuss how confidence shaped Lena’s experience.
• 08:29–09:05: Exchange on gender expectations and “boob math.”

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5. Takeaways

• Throwing yourself back into dating after heartbreak can boost confidence—especially with multiple options.
• The order or number of dates doesn’t matter as much as the personal growth gained from putting yourself out there.
• Honesty and self-awareness are key, but sometimes a little discretion is wise.
• Traditional dating rules are ripe for creative, self-empowering twists — with a healthy dose of humor.
• Gender double standards persist, but context and intention do matter.

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Memorable Moment:
Friday Guy “wins” Lena’s heart — reminding listeners that sometimes, you need several chances to get that one great match. The journey, and the laughs, are just as important as the outcome.

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Hosts present: Bert (Host A), Kristin, Abby, Cassie, Tommy, and the whole Bert Show cast.
Listener involved: Lena

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Transcript

[A]

The Burt Show. Good morning, Lena. You're on Q100. How are you?

[B]

Hi. I'm good.

[A]

All right. Tracy tells me that you got a one year anniversary coming up this weekend. But it's not like, oh, we've been.

[B]

Together for a year exactly. It's. It's a breakup anniversary.

[A]

A breakup anniversary. All right, well, first we have to have a little history here. How long were you going out with Dude?

[B]

For three years. And then we broke up almost a year ago. And just like the past year, I've just been miserable and I haven't been dating. I've like. And Valentine's Day was just, I guess when I hit bottom. And now I'm like, you know what? Forget this. I'm not going to mope about this guy anymore. It's over. I'm getting back out there and I have. I have four dates lined up for this weekend.

[C]

This is the way to come out here.

[D]

Is that intentional or is that accidental that they all happen this weekend?

[B]

No, it's intentional.

[A]

Now you say you have or have not been dating up until this point. Like, will these be your first four dates after the breakup from last?

[D]

Yeah.

[B]

So it's like four years since I've been out there.

[A]

Now, on paper, I love this because it seems like a great idea. And if you're gonna come out of this thing, come out of it strong man. Four days.

[E]

Exactly.

[A]

It's one after the other because one won't do it.

[D]

It's a slump buster.

[A]

It's four straight days of slump busting. So we figured this could go one of two ways. Either, you know, you're gonna kind of like force yourself into getting over it, even though it's been a year, get yourself over it and start getting out there. Or after the second date, you're gonna be miserable going, this is the best Atlanta has. This is it. I think back in this world right.

[C]

Now, I think it would be. I think that would happen if it was only six months or less. But I think after a full year, she was obviously ready to. Ready to move on. That's why she initiated all this. I think that we had mentioned before that it's smart to have four dates in a row, because the first one, like you said, if it's just one, it would be awkward. It'd be weird. She's like, you know what? Forget this. Forget this. I'm going back doing whatever I was doing. But four in a row, by the third or fourth date, it should have been fun.

[A]

By that point, you would think you would Think. Hey, Lena. Good morning. You're back on Q100 and the Burt Show. What's up?

[B]

Hello. How are you?

[A]

Good, how are you?

[B]

I'm actually good.

[C]

Good.

[B]

I did well.

[A]

You did well. All right, let's go through all of these one at a time here because there were four lined up and these were supposed to be on four consecutive days, right?

[B]

Yes. It was like a marathon. Okay, so the first one, the first one was pretty casual, which was fine, which is a good way to start. It was really like a happy hour and like a happy hour date. And I brought my friends and he brought his. So it wasn' it wasn't even really like a date.

[C]

All right.

[A]

Okay. And let me ask this one more time. And I know you answered this. I just can't remember how you did. Did you line these guys up from least excited about to most excited about?

[B]

I didn't know.

[A]

Okay, that was your suggestion.

[B]

You know, that was a good suggestion. But no, I didn't get a chance to do. I just kind of grouped, you know, threw them all in there. So anyway, this was the co worker, so it was cool that it was like no pressure and we didn't really hit it off. So it was fine. And so it was kind of like we can act like we didn't even go on a date. How won't be weird.

[A]

How long did this like group date last?

[B]

It was probably. It was like from about 6:30 till like 10 or a little bit after.

[A]

Three and a half hours. Yeah, three and a half hours.

[B]

You can never have fun. I mean, we all had a good time, our friends got along, you know, so it was like. It was cool, right? But definitely not really a date.

[A]

Okay, this is, this is why. This is why as a sidebar here, the whole world just listen to me about dating. You have to come on it.

[E]

You're so exhausted by this, you're just listening.

[D]

You're exhausted by people who just don't pay attention.

[A]

And these ideas are so out of the box that they'll never be adopted. But if we could just check in with each other on 30 minute increments on dates and each has the right to say, look, this is either going great or you know what, you seem like a great person, but you're just not for me. And you walk away with no social repercussion. That's three hours out of your life that you could have saved. And here's three and a half hours on a dude that she's never, never going to go out with again.

[C]

One Is a group thing too, is a co worker. So there was. There would be repercussions with the co first. I mean it is kind of a risky idea to go out with a co worker. But I do think she handled it well. I do think the first time out it was group co worker. Cool. Everything's easy. I see what you're saying. In any other situation, very high schooling, it's 20 something.

[A]

Yeah.

[C]

Now you know that do this. And I think it was good for her to do that the first time out.

[A]

And the group data safe. That's a nice safety net right there.

[B]

Totally safe. But Friday night I had a real date and I really like this guy.

[A]

He.

[B]

He picked me up like 8 o'. Clock. We went out for dinner, then went out for drinks after we were together till like I didn't get home till like 3:15.

[C]

Oh nice.

[B]

Okay, okay, so that one was nice. And we had a little kiss in the car. So that was good. But I really like this guy. Like this guy wins.

[E]

Friday guy wins.

[A]

He won Lena idol.

[B]

He's the only one I'm going out with again. But anyway, okay, so Saturday was. Saturday was high schooling. We went out for dinner and a movie and it was just. The conversation was boring. I felt like I was kind of on an interview. Like it was just. It was just no chemistry questions. But no chemistry. Yeah, it was just bad.

[A]

See here again with the half an hour contract would have saved me. Yeah, right. You agree and he agrees at half an hour that look, this isn't going to work so let's just go our separate ways and you save all that time on your deathbed.

[B]

And then, then Sunday I. I was. I guess after the Saturday date I was like, you know what? I can't risk another date. That's bad. So I canceled the Sunday guy and I called the Friday guy.

[A]

Yeah, three and four never had a chance if two was that great.

[C]

Y.

[B]

But we had a great time. We went out for brunch and then we went to a movie after we spent like all of Sunday together. But the funny thing is is that we saw the same movie Sunday that I saw with the bad date on Saturday.

[C]

Well, at least cleanse the experience.

[B]

What?

[C]

That's it. At least cleanse the experience of a bad day.

[B]

Did you pretend like you pretended like I hadn't seen it? Because I didn't tell him. I don't want to tell him. Like, oh, I was on four dates this week. You know what I mean? So I just kind of. I'm not gonna tell Him.

[A]

There is a certain amount of, like. Because I really believe if you're single, that you should be able to tell other people that you're dating somebody else. You know, just so long as you're honest about it. But I think if you come back with a number that is, like, four in four days, I think that's pretty much a turn off for just about any guy.

[B]

I do, too. It'll be our secret.

[A]

So you will continue to pursue number two.

[B]

Yes.

[C]

Good for you.

[E]

Friday guy is winning.

[A]

Yeah.

[D]

And he'll always be known as Friday Guy.

[A]

Yeah.

[D]

Like, when you go on moment of truth. Were you ever in love with Thursday guy? That'll be your question.

[A]

So I guess the lesson to be learned here is there is, like, some kind of comfort in numbers that if you throw enough out there, at least one out of four days has to be, like, follow up able.

[E]

And who knows? It could have been the confidence that she brought, you know, with having four dates lined up and just sort of that air of confidence, like, oh, well, if this doesn't work, then something else will. And maybe it's that confidence that made.

[B]

It so great with Friday Guy that definitely helped. Yeah.

[A]

This goes along with the mojo conversation that we had earlier this morning. This confidence conversation that we had earlier this morning also, because this seems to be such a large part of dating and feeling good, obviously, about yourself is confidence. And we. We tried this experiment earlier this morning with great success. Also. Yeah.

[E]

With the lingerie thing, where women that were single were wearing their sexier lingerie to bed at night just by themselves and just tried it for a week to see if it changed their confidence throughout the day. And all three of them said it worked, right?

[A]

Yeah. So you combine that with the advice that you're giving. Like, I mean, I had a whole bunch of dates lined up, and here it made me more confident because if Thursday didn't work out, I had Friday lined up.

[E]

Right.

[A]

Because inevitably, with this dating, it's all about confidence and how you're feeling about yourself.

[B]

It definitely is. Yeah.

[C]

And I'm glad you did it, because if you had just gone on that first date, if you had just set one thing up and it was that first one, then, you know, it would have been back to square one.

[B]

Totally. I would have been so discouraged because I would been like, oh, it's not even a real date. This is how people date nowadays. You know, I mean, like, group dates. Because it was his idea. I was like, ooh, I bring some of my friends. And I was like, all right, Whatever.

[A]

That's nice. It's a safety net now. I wonder if we're having the same conversation with a guy. Does it feel the same? Does it have the same texture? Or would you guys be all over him going, ah, stop being a whore. You have four women lined up in four days. Or does it work both ways?

[E]

I think it works both ways. Especially if he had been out of the breakup and had a miserable gear like she did.

[D]

You know, it also depends on anyone and what he says his intentions are. He's like, yeah, we get four times this weekend. But if he's like, I'm gonna go out with four different girls and I want to pick which one of these I like the best, and then that's who I'm. You know?

[A]

Right.

[D]

Then I think that's a different. But guys wouldn't say that.

[A]

That's eight boobs. Boob math. It always comes down to boob math for us. All right, Lena, thank you very much for the follow up. I like to hear that. Thanks so much.

[C]

Okay, cool.

[B]

Thanks, guys.

[C]

Congratulations.

[E]

Yeah. Hope it goes well.

[A]

Yeah. Call us from time to time and let us know how it's going with Friday guy.

[B]

Okay, I will. Totally. Thanks.

[A]

All right, Lena. Thank you. The bird show.