Vault: She's Playing Two Guys at Once and Needs Our Help

Summary

Podcast Summary: The Bert Show – "Vault: She's Playing Two Guys at Once and Needs Our Help"

Original Air Date: March 20, 2026

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Episode Overview

This episode of The Bert Show digs into a familiar, modern dating dilemma: a listener, a single 26-year-old woman in Atlanta, seeks advice on how to gracefully juggle two men—especially with Valentine’s Day looming. The Bert Show crew and callers weigh in with humorous, candid, and occasionally conflicting perspectives on honesty, logistics, and the gender dynamics at play.

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Key Discussion Points & Insights

The Listener's Email (01:00)

• Situation: The listener is dating two polar opposite men. She hasn’t misled them about exclusivity, but suspects each believes he’s the only one. With Valentine’s Day on a Saturday and both vying for plans, she’s in a bind—already committed to dinner with one but lately more interested in the other.
• Dilemma: How to manage Valentine’s without lying or breaking things off—does she see both, and how does she explain herself?

Panel’s Immediate Reactions

• Juggling Both Dates (02:35):
  • Male panelists muse about squeezing both dates into the same day (e.g., dinner with one, late night with the other). Consensus: On Valentine’s, dinner is essentially a full-night commitment, making this difficult.
• Intimacy and Commitment:
  • They reflect on whether she has gotten intimate with either—suggesting the answer might dictate how easily she can pivot between the men.
  • Quote:
    "If she's committed to one for dinner, which is what I think her email said, guy number one is getting dinner, but guy number two she likes more." (03:02, Male Panelist 2)

Honesty vs. Strategy (04:41)

• Host 2 on honesty:
  "Honesty in this case is great. If we know that a woman is dating me and dating somebody else, it makes you the hotter commodity. The chase is what we need." (04:41, Host 2)
• Men are more competitive if they know there’s another contender. The suggestion: don’t lie—tell guy #2 she already has plans, and he’ll work harder.

Alternative Solutions

• Friday Night Solution: (05:16)

  • Several panelists and callers suggest celebrating “Valentine’s” with one guy on Friday, keeping Saturday for the other. This allows her to maintain honesty and avoid overlap.
  • Caller anecdote:
    "Valentine's the night before, I spent the night with one girl, woke up and made breakfast for that morning and went out and had lunch that day and then went out that night with another girl, ended up getting married to the girl that I went out the first night with." (05:46, Caller 3)

• Panelist Endorsement:
  "It's actually would work to her advantage if she actually blows off the one she likes more on Valentine's night. If she does it properly... He's gonna work so much harder because you just made him second." (05:16, Host 1)

Creative Excuses and Caller Input

• Caller Ideas:

  • Spend Friday with the man she wants most, then regroup and enjoy dinner with the other Saturday night. “If I can accomplish this across state lines, I’m sure she can accomplish it in one.” (06:25, Caller 2)
  • Tell one you’re “spending Valentine’s with your mom”—panel is amused but notes this is classic guy move, and the listener wants to avoid lying. (07:02, Caller 4)
  • Host Commentary:
    "If you're dating a girl who chooses to spend Valentine's Day with her mom, get out of the relationship, she is crazy." (07:40, Host 1)

• Wing-woman Strategy:
  Go to a girls’ event like Bitterball, say you’re helping a lonely friend, then go out with one guy Friday and one on Sunday. (08:08, Caller 1)

Bottom Line: Panel Advice (08:28–10:09)

• Unanimous Advice: Stay honest, be clear you’re booked Saturday, and see the other guy Friday.

• Host 2:
  "There's no reason to be dishonest. Tell him that you've already got something lined up for Valentine's night, and ... he'll make Friday night way better." (08:55, Host 2)

• Panelist humor about men and women’s thinking:
  "Way better. And it is physically impossible for a woman to dumb it down to a guy's level. You guys are incapable." (09:07, Host 1)

• Final Consideration: Panelist quips — just choose by asking, "Who do I want to wear the prettiest lingerie for?" (09:59, Male Panelist 2)

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Notable Quotes & Memorable Moments

• Host 2 (04:41):
  "The chase is what we need."
• Host 1 (05:16):
  "It’s actually would work to her advantage if she actually blows off the one she likes more on Valentine’s night."
• Caller 3 (06:01):
  "Ended up getting married to the girl that I went out the first night with."
• Caller 2 (06:25):
  "If I can accomplish this across state lines, I’m sure she can accomplish it in one."
• Host 1 (07:40):
  "If you're dating a girl who chooses to spend Valentine's day with her mom, get out of the relationship, she is crazy."
• Host 1 (09:07):
  "It is physically impossible for a woman to dumb it down to a guy's level. You guys are incapable."
• Male Panelist 2 (09:59):
  "All she has to ask herself is, who do I want to wear the prettiest lingerie for? And then she has her answer."

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Timestamps for Key Segments

• 01:00 – Letter from listener: juggling two guys on Valentine’s Day
• 02:35 – Initial panel responses, logistics of double-dipping
• 04:41 – Panel and host agree: honesty is the best policy
• 05:16 – Strategic suggestion: give the more-desired guy the “exclusive” Friday night
• 06:01–06:59 – Callers share firsthand stories & advice
• 07:40 – Panel jokes about “Valentine’s with mom” excuse
• 08:28–10:09 – Panel consensus: stay honest, work the schedule, don’t overthink it

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Conclusion

With humor, candor, and plenty of real-life anecdotes, The Bert Show panel encourages honesty and smart scheduling. Their advice: don’t lie—if you’re dating two guys, be up front and use the calendar to your advantage. And above all, don’t stress: if Friday night is good enough for one, the other will rise to compete. As always, laughter, good-spirited jabs, and a dash of cheeky wisdom make the episode both insightful and entertaining for anyone navigating modern dating’s trickier scenarios.

Transcript

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[Host 2]

The Third show this is the email that came in a couple of days ago and I think a couple of you guys are gonna be in the same situation where you're dating like two different dudes or two different women on Valentine's Day and you're not exactly sure how to handle it. So if you've gotten through this process before unscathed and give us a call and give us some advice here. Email reads like this. I used to think that this was exactly the type of problem that I would want to have, but now I have no idea how to handle it. I'm a completely single 26 year old female in Atlanta and I'm enjoying the dating scene. I've been dating two guys and really enjoying each one of them for completely different reasons. They're polar opposites and I think that this is why I'm still interested in both guys. I've led neither one of them to believe that I am only dating them and it has never really come up. But I but I really think that each guy believes that they are the only one. Surprisingly, I've had a fairly easy time dating both without any scheduling issues. But as you know, Valentine's Day falls on Saturday this year and both have discussed doing something.

[Host 1]

Uh oh.

[Host 2]

One has already asked me to dinner and the other one assumes that we will be going out. I told guy number one that I would go out to dinner, but I have started to like guy number two a little bit more since then. Hmm. I've not lied to either guy thus far and certainly do not want to start now. I'm not really ready to break it off with either one, but I don't really see a way around it. Since I will have to tell one that I have other plans on Valentine's Day. I thought it might be nice to get some strangers and get some guys advice also. So how do you handle it now?

[Male Panelist 1]

She's already committed to dinner with one. Because the first thought I had is you can somehow see them both on the. Because Valentine's Day is 24 hours long, you know. And you don't think so.

[Host 2]

That's tough. Well, you'd have to make, I think you'd have to make, I mean, not at the same time decision on who you want to get, who you'd be more comfortable with getting intimate on that day. Because that's the second date.

[Male Panelist 1]

Well, she's already. I mean if she's committed to one for dinner, which is what I think

[Male Panelist 2]

her email said, guy number one is getting dinner, but guy number two she likes more.

[Male Panelist 1]

Cause you can't get back out of

[Host 2]

dinner and, and dinner should. Dinner should continue on late.

[Host 1]

Yeah.

[Male Panelist 2]

You can't just end it.

[Male Panelist 1]

So her issue really is I've committed to dinner with one guy, but I want to be with the other one until.

[Male Panelist 2]

But she doesn't want to break it off with either one. Right.

[Male Panelist 1]

Okay.

[Host 2]

So unless she goes to dinner, she's

[Male Panelist 1]

about dinner dates and she wants to end the night with one.

[Host 1]

But I think the point is on Valentine's Day the dinner commitment is a night commitment.

[Host 2]

Right?

[Male Panelist 2]

I would agree.

[Host 1]

You don't like. On a regular Saturday night, I think you can do a 7:30 dinner and then at like 10 o', clock, say hey, hey, you know what, I gotta go tired early tomorrow, whatever, bail, and then by 10:45 be at a different bar with a different dude.

[Host 2]

I also think we're missing one key detail here. If she has already gotten intimate with the guy that she's having dinner with, then it gets weird to break off. Then the date should continue through the night. But if she hasn't, she can cut that to just dinner and then call the guy that she really digs to come over for Valentine's day. Booty call.

[Male Panelist 1]

Yeah. To me, the only thing that she. Yeah, she's made her commitment for Saturday night.

[Male Panelist 2]

Yeah, it's already done the whole night. She can't go after dinner and do something else because then booty Call guy knows he's just a booty call because he wants to do dinner with her too.

[Host 1]

Guess what? He don't care.

[Host 2]

He wants a booty.

[Male Panelist 2]

Well, not all guys are that superficial.

[Host 1]

Yes, they are.

[Commercial Announcer 1]

What about one guy on Friday night? What about celebrating on Friday night with the other dude?

[Commercial Announcer 2]

There's a good say you have to work on Saturday.

[Male Panelist 1]

Well, she said she's never lied. That's the thing. Because I was like, she could do a picnic with the other dude during the day and then have dinner with the other at night and, you know, and have an excuse why she can't do it Saturday night.

[Male Panelist 2]

But.

[Host 2]

And Jeff and I have tried to explain this to women before also, that honesty in this case is great. If we know that a woman is dating me and dating somebody else, it makes you the hotter commodity. Don't try to lie to sort of help our feelings out. We don't tell us. Just be honest with us. The chase is what we need.

[Male Panelist 1]

Well, then she should just tell the other guy Friday night. I've already got plans Saturday night. And leave it at them then, based on that theory.

[Host 1]

And then you know what? It's actually would work to her advantage. Let's not even take calls from listeners. We got it all.

[Male Panelist 1]

We got this one.

[Commercial Announcer 2]

Everybody.

[Caller 1]

We got it.

[Host 1]

You know, go home, people. But it would work to her advantage if she actually blows off the one she likes more on Valentine's night. If she does it properly. Like, I think telling him Valentine's morning or Friday night, bad. But if she's like, I'm sorry, I've already got something going on on Saturday night, then he's gonna be like, wait a minute. And if he's into her, he's gonna work so much harder because you just made him second middle for Friday night. Valentine's night.

[Caller 2]

Yeah.

[Male Panelist 1]

Yeah. To be honest. Yeah.

[Host 1]

Booyah.

[Host 2]

Hey, Tom. Good morning. You're part of the bird show. Hi.

[Host 1]

Go ahead. Beat that advice, Tom.

[Caller 3]

Yeah, I had the same thing happen in the Valentine's the night. The night before, I spent the night with one girl, woke up and made breakfast for that morning and went out and had lunch that day and then went out that night with another girl, ended up getting married to the girl that I went out the first night with.

[Host 1]

It's actually a good trick because if you go out Friday night, you could say, but then we get to wake up Valentine's morning together.

[Host 2]

Ah, it's good.

[Male Panelist 2]

It's good.

[Male Panelist 1]

Mm.

[Host 1]

Mm. Oh, you're still gonna take calls? Okay. Good luck.

[Host 2]

Hey, Lori, you're on Q100. Hi.

[Caller 2]

Hi, Bert. Hey, Jen. Melissa and Jen.

[Male Panelist 1]

Hi.

[Host 1]

Hi. Hi, Wendy.

[Host 2]

Hi, Wendy.

[Caller 2]

I love you, too.

[Host 2]

What's up, Laurie?

[Caller 2]

Well, actually, I've done this several times across state lines. On Friday night, she spends the night with the guys who she most wants to be intimate with, get the job done, have breakfast, maybe even, you know, go spend some time together during the afternoon. Then she can get herself together for dinner with the other gentleman Saturday night. And if she chooses to be intimate with him, there's still the 24 hour break period. And if I can accomplish this across state lines, I'm sure she can accomplish it in one.

[Male Panelist 2]

She's professional.

[Male Panelist 1]

Yes.

[Host 2]

Hey, Jay. Good morning. You're on Q100.

[Caller 4]

Hey, good morning. First, I want to tell you guys I love the Q100 girls. Secondly, what I do is the girl I want to spend the night with more, I tell the other one that I spend Valentine's day with my mom and I spent and that they love that. Romantic.

[Host 2]

So he's actually building points by lying. That's such a dude way to handle it, though.

[Male Panelist 2]

I love his honesty because now everybody listening knows that that is crap if you're hearing that.

[Host 1]

But the difference is you're playing the role of a guy. She said she's never lied to either of the dudes. She can't say that.

[Host 2]

And we're saying she doesn't have to.

[Host 1]

And just so you know, if you're dating a girl who chooses to spend Valentine's day with her mom, get out of the relationship, she is crazy.

[Male Panelist 2]

Well, I mean, you could say the same thing for a guy.

[Host 1]

Nah, a guy, it's sweet and endearing.

[Male Panelist 1]

Sweet, kind of chivalrous.

[Host 1]

My mom is older and she's alone, so I'm gonna spend Valentine's day with her.

[Male Panelist 2]

Yeah, that's fine.

[Host 1]

But then if a girl.

[Host 2]

Don't believe it, girls, because you're building points in your life, awful, but brilliant. Good morning, Julie, you're on Q100.

[Caller 1]

Hey, love you guys.

[Host 2]

Thank you.

[Caller 1]

She can't. She doesn't have to lie. She's single. She's 26. Give her some tickets to Bitterball. Have her tell both guys. My girlfriend's really lonely, she needs to find a guy. I'm gonna be her wing girl for the night and go to Bitterball with her. And then she goes out with one guy on Friday night and the other guy on Sunday night.

[Host 2]

Still don't need to lie though.

[Male Panelist 1]

No. And I think she wants reason to lie. There's no reason why she can't, you know, get the full benefits of Valentine's Day because she's got two guys that want to spend it with her? I. I think that it's like you said, if honesty's not going to hurt her, then why not be honest? She's already made a commitment Saturday night, and then, you know, Friday the 13th.

[Male Panelist 2]

I think that we think men are going to respond in the same way that women would respond to that.

[Host 2]

The problem with a woman is that you're thinking like a woman, right. And you got to think like a guy here.

[Male Panelist 1]

And it got. Yeah, it'll be better if you tell

[Host 2]

him the truth, because she's been so honest up to this point right now. There's no reason to be dishonest. Tell him that you've already got something lined up for Valentine's night, and like Jeff said, he'll make Friday night way better.

[Male Panelist 1]

Right?

[Host 1]

Way better. And it is physically impossible for a woman to dumb it down to a guy's level. You guys are incapable. You hit.

[Male Panelist 1]

We're too smart.

[Host 1]

You hit a certain level on the. You know that scale they show you in the old school books of how man developed, you know, and there's the

[Host 2]

dude dragging his knuckle, dragging your knuckles, the evolution chart.

[Host 1]

Like, women won't go past that. Like, it hits a wall. You got to turn one page back and see the part where we're just floating in the pond like little algae turd. Then you're thinking like a guy.

[Host 2]

You need a good guy friend to dumb it down for you, and you can even call him up and go, look, I need you to dumb this down for me. Help me out.

[Male Panelist 1]

I'll handle it.

[Host 2]

Yeah.

[Male Panelist 1]

So basically, our advice to her is tell him the truth and go with the other dude on Friday night.

[Host 2]

If you tell. If you're being honest with a guy, if you're dating two dudes, if you are honest with both of them, they are gonna compete even though they don't know each other. Indeed, they will compete with each other for you.

[Male Panelist 2]

Or if she's in the place where she just wants to pick one, all she has to ask herself is, who do I want to wear the prettiest lingerie for? And then she has her answer.

[Host 2]

Is that it right there?

[Commercial Announcer 2]

That's it.

[Host 2]

Pretty simple. Slam dunk right there.

[Commercial Announcer 1]

She's gonna get some awesome Valentine's Day presents.

[Host 2]

She will. Especially from Friday night guy.

[Male Panelist 1]

Two nights of Valentine's Day. Yeah, that's for sure.

[Male Panelist 2]

I hate her.

[Host 2]

The bird show.

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