Vault: His friend is encouraging him to cheat

Summary

The Bert Show
Episode Title: Vault: His friend is encouraging him to cheat
Air Date: June 3, 2026

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Episode Overview

This episode dives into a listener’s dilemma: his friends are urging him to cheat on his long-term girlfriend, suggesting it might help him decide if he’s truly ready for marriage. The cast debates whether cheating ever benefits a relationship, shares personal stories and listeners’ calls, and explores themes of curiosity, commitment, and honesty when faced with doubts about long-term partnerships.

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Key Discussion Points & Insights

1. The Listener’s Dilemma (00:35–04:09)

• Summary of the Listener’s Email:

  • A 23-year-old man, with his high school sweetheart for 6 years, is unsure about marrying her despite loving her deeply.
  • Friends advise him to cheat, claiming it might help clarify his feelings or readiness for marriage.
  • He has always been faithful, but feels pressured by indecisiveness and external advice.

• Cast’s Initial Reactions:

  • Bert (B): “Your knee jerk reaction here is going to be to call up and say never, never, never, never cheat. Never, never, never, never. That’s too easy. ... But there’s gotta be some people out there that think that there are some times where cheating on your significant other is actually healthy for the relationship.” (00:41)
  • Kristin (C) and others immediately say he’s not ready for marriage if he’s even considering cheating.

2. Is Cheating Ever “Healthy” for a Relationship? (04:10–05:20)

• Personal Experiences from the Hosts:
  • Bert shares a story about a friend whose secret infidelity supposedly strengthened his marriage:
    • “He never tells her about it. And the relationship, the marriage ended up fine. And he credits him checking out and having this side relationship for making him realize what he wanted and committing, recommitting back to his marriage. ... And he said it was actually good for their marriage.” (04:09–04:43)
  • Kristin: “It’s only good ‘cause she didn’t find out.” (04:47)
  • The cast agrees secrecy often plays a crucial role in whether cheating is “forgiven” or ruins the relationship.

3. Listener Calls: Real-Life Stories

A. Last-Minute Cheating Before Marriage (05:20–06:30)

• Caller Kim: “A week before I got married to my husband, I did cheat on him... All it did was make me realize that I did love my husband. ... I had waited probably about three or four years after we were married. I told him...and he handled it fine. ... It ended up making the relationship better.” (05:20–05:55)

• Hosts question if her husband’s calm reaction means he might have done something similar. Kim says, “I really don’t think I would have [been mad].” (06:22)

B. Cheating on a Break Catalyzes Commitment (07:01–08:22)

• Caller Courtney: Her now-husband repeatedly broke up with her to “have fun,” so she finally slept with his “arch nemesis.” This time when he returned, she confessed, and he proposed soon after.
  • “So I actually do think it helped.” (07:58)
• Cast notes this isn’t exactly cheating since they were technically on a break.

C. Curiosity Before Commitment (08:25–10:36)

• Caller Sarah: Engaged after 6 years together, but cheated to resolve lingering curiosity.
  • “A couple weeks ago, I cheated on my boyfriend with [another man] because I just needed to know. And actually, it’s completely made me know that I need to be with my boyfriend.” (08:31–09:10)
  • She doesn’t plan to confess.
• Cast suggests she may need more time before marriage and discuss whether some people truly lack curiosity or rebelliousness.

D. Ongoing Affair and Marital Turmoil (10:39–12:47)

• Caller Ashley: Reconnected with an old boyfriend during marriage struggles. Filed for divorce, had an affair, then returned to her husband.
  • “Honestly, ever since I reconnected with [the old boyfriend], my relationship with my husband has been so much better.” (11:24–11:37)
  • The group tries to clarify the timeline and impact of her parallel relationships, eventually concluding her situation is complicated and tenuous.

E. The Lingering Impact of Curiosity and Guilt (13:01–14:07)

• Caller Laurie: Grew up religious, married young, her husband cheated, she stayed curious about other experiences. Post-divorce, she dated widely.
  • “I think if you get back in the relationship after you’ve cheated without telling the other person, there’s always going to be that negativity there... I don’t know that you can have a full 100% relationship with somebody based on a lie.” (13:36–14:04)
  • Her advice: “If you cheat, you got to come clean.” (14:07)

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Notable Quotes & Memorable Moments

• Bert: “You can't cheat to stay within the relationship. You can't have it all the ways here. You're not mature enough to be married yet.” (03:06)
• Kristin: “If you tell your partner that you are cheating and their reaction is, oh, it's okay, it's cool. You have to sort of wonder... if they're saying that just because they're rationalizing that they cheated, too.” (06:36)
• Sarah (caller): “I cheated on my boyfriend with [another man] because I just needed to know. And actually, it’s completely made me know that I need to be with my boyfriend.” (09:10)
• Laurie (caller): “There’s always going to be that negativity there that I don’t know that you can have a full 100% relationship with somebody based on a lie.” (14:04)

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Key Timestamps

• 00:35: Introduce the dilemma: friends urging to cheat for clarity
• 01:42: Listener’s email read and discussed by the cast
• 04:09: Bert shares a friend’s marriage improved (secret) by cheating
• 05:20: Kim’s confession: last-minute cheating before wedding
• 07:01: Courtney’s story: infidelity on a break leads to future proposal
• 08:29: Sarah: cheating for curiosity before commitment
• 10:39: Ashley: affair during marital crisis, returned to husband
• 13:01: Laurie: growing up religious, impact of curiosity, honesty after infidelity

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Conclusion & Takeaways

• The hosts and callers widely agree: if you feel compelled or pressured to cheat, you’re not ready for marriage.
• Some callers share stories where infidelity led to self-discovery or even strengthened relationships, but this only happened under specific, usually secretive circumstances.
• The risk and aftermath—especially regarding honesty and guilt—are significant and lasting.
• Final consensus: Cheating rarely “helps” in a healthy way; resolving doubts through honesty and self-reflection (or a clean break) is the wiser path.

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For further discussion or to get involved, listeners are invited to call or visit The Bert Show website.

Transcript

[A]

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[B]

American express my los pro rewards encompras elle hibles gana tres puntos porcada do las dunant los primero seis american express. Business Credit it's the Virt show. Okay, I know your knee jerk reaction here is going to be to call up and say never, never, never, never cheat. Never, never, never, never. That's too easy. I'm curious if there is anybody listening right now and we can use the voice disguiser for this. 404-741-Q100 and I'll even say going into this that I'm sure 98% of the calls would be never, never never never cheat. But that, I mean if we take 10 calls saying that. Not real entertaining. But there's gotta be some people out there that think that there are some times where cheating on your significant other is actually healthy for the relationship. Because this is the advice that this. Dude, where'd my voice go? Melissa?

[C]

What'd you do, rub it off?

[B]

Picked a bad time to lose my voice with 10 minutes left. Let's talk about Jeff. Here's how the email reads. I'm a 23 year old man and I've been in a relationship with my high school sweetheart for six years. Our relationship has had its ups and downs as any relationship would, but we're still very, very much in love. Over the years, I've had open opportunities to cheat, but I've always remained faithful. I realized that this is the woman I want to spend the rest of my life with. But there's a part of me that's very indecisive. It's reached a point now where she's ready to get married and have kids and, and I feel like I'm still real young. We've got all the time in the world and why not just enjoy each other for now? The advice I've been getting from my buddies is that I need capital letters to cheat. They think that by cheating it'll help me realize that what I want, whether it be single life or married life. Anytime my girlfriend and I ever try to take a break from each other. I always wind up doing whatever possible to get her back. I know if we break up, that's exactly what I'll do. Again, is in this situation, should I cheat? If not, what should I do? I think if we take a hundred calls, 100 people are going to tell, you're not ready to get married. Right.

[C]

Well, he's obviously not ready yet.

[B]

You're not ready. You know, you're not ready.

[D]

Well, that's what he said.

[C]

He's not ready.

[B]

You're not ready.

[D]

But he doesn't want to lose her.

[B]

But he doesn't want to lose her. So you can't. You can't cheat to stay within the relationship. You can't have it all the ways here. You're not mature enough to be married yet.

[D]

Yeah, they've got to just take a break. I mean, he's just got to be honest with her that they've got to. They've got to take a break from

[B]

each other or he's always going to wonder one way or the other. Although he says every time they break up, he always goes back to her. So he just has to commit one way or the other.

[C]

Yeah, he has to.

[B]

Cheating on her isn't going to help the situation. Right.

[C]

Yeah. I mean, I'm one of the. I would be one of those people that would call and say never. I mean, because it's not. It never helps. I mean, you think it might, but I think the repercussions are stranger than you expected. You know what I mean?

[D]

I think if you had given us a different scenario and she had cheated on him and he was thinking about balancing it out. I do have a friend who had her boyfriend cheated on her and she never really. She stayed with him and never really ever got over it and always thought, well, maybe I should. You know, she was like, maybe I should have done it back to him, revenge cheating and would have, like, balanced it out or something.

[B]

I have a friend that's been married for roughly the same amount of time that I've been married. And their marriage went through a real rough spell a couple of years ago. And he ends up screwing around on his wife for a couple of months. He never tells her about it. And the relationship, the marriage ended up fine. And he credits him checking out and having this side relationship for making him realize what he wanted and committing, recommitting back to his marriage. His wife never knows about it.

[E]

Wow.

[B]

And he said it was actually good for their marriage.

[C]

Wow.

[B]

Yeah. So that's why I'M asking the question this morning. Is there anybody listening?

[D]

It's only good. Cause she didn't find out.

[B]

But she didn't find out. And he said the relationship is stronger now. It made him recommit. So the infidelity actually worked for him in this case.

[D]

And he should never, never, never, never, never, never, never, never, never tell her.

[B]

I'm telling her that now.

[C]

No, you better hope, like, that mistress doesn't tell either, ever, ever, ever.

[B]

And she hasn't up to this point. So that's really the question is, and we're only going to take these calls and is it ever? Okay. Does it actually help in some cases to screw around? And these could be dangerous here. Hey, Kim. Good morning.

[F]

Hi.

[B]

Hi. You're on the voice disguiser.

[F]

Okay. I've been married now for almost 26 years. But a week before I got married to my husband, I did cheat on him. And all it did was he was working out of town and I went out with a guy that I had liked for a long time. But all it did was make me realize that I did love my husband. And I had waited probably about three or four years after we were married. I told him all about it, and he handled it fine.

[B]

And it ended up making the relationship better.

[F]

Yeah, for me, it did.

[E]

Wow.

[C]

And it was while y' all were still together, you weren't on a break?

[F]

It was. No, we were. It was a week before we got married, and he was traveling at the time, and I was 17 and scared to death and didn't know if I really loved him or not. But it made me realize I did.

[C]

Now, do you. Let me just throw this out there.

[F]

He.

[C]

Do you think he was okay with it? Because he may have done the same thing. And would you be mad if he did?

[D]

Good question.

[F]

You know, I really don't think I would have. Not after all this time that we've been married. Because like I said, it was right before we got married and we were both still young, I don't think it would really make me mad.

[B]

Yeah, I'm with Melissa. Like, if you tell your partner that you are cheating and their reaction is, oh, it's okay, it's cool. You have to sort of wonder, I wonder if they're saying that just because they're rationalizing that they chew to cheated, too, and now they feel like it's an even playing field.

[C]

Yeah, it's fine. It's off my head, you know?

[B]

404,741,Q100. If cheating is okay. Hey, Courtney, go ahead, you're on Q100.

[F]

Hi, how are you?

[B]

Good, how are you?

[F]

I'm doing very well, thanks for asking.

[B]

What's up?

[F]

I will tell you. My husband and I have been married for 10 years, and before we got married, there was a time period where he would, like, love to just go out and, you know, have fun on the weekends and get some strange or whatever you would call it. And he would break up with me, and we ended up breaking up about four or five times. And the last time he did it, I was just done. I had just checked out, and I was finished. So I went and found his arch nemesis, I guess you would call it, and had a little too much to drink like everybody does, and we ended up hooking up. Well, after that, about two weeks later, he did the normal thing of calling me and asking me if I wanted to get back together and blah, blah, blah. Of course I said yes, like I always did, and I ended up telling him about it. And that actually made him propose to me because he realized that that last time was it for me. So I actually do think it helped.

[B]

That's like the ultimate gamble right there. Like, if you put all your chips in, you go and you sleep with his arch nemesis, you tell him about it, and it shocks him into it.

[D]

Yeah, she was over it.

[F]

Anyway, I was not really guilty about it, so I didn't have, you know, I had to tell him. There was, like, really no choice. So when you find out, they were

[C]

on a break, too, so it's not necessarily cheating. You weren't in the relationship. So break up and then do what you got to do and then realize what you have.

[B]

So technically not cheating.

[D]

Technically not.

[B]

Here is Sarah. Good morning. You are on Q100. Hi.

[F]

Hi.

[B]

Hey. You're on the voice disguiser.

[F]

Okay. Yeah. Basically, this is my exact situation right now. I have been with my boyfriend for about six years, and we are engaged. And I kind of. I'm only 25, so I kind of feel like I needed to kind of get out there and play the field a little bit more before I made that huge of a commitment to get married. And I just. There was this guy that I had known for a while, and just a couple weeks ago, I cheated on my boyfriend with him because I just needed to know. And actually, it's completely made me know that I need to be with my boyfriend.

[D]

Have you told your boyfriend what happened?

[F]

No, and I'm not going to.

[B]

You're not going to plan on telling him? You wouldn't give her that Advice. You would say, tell him.

[D]

I would say she needs some more time to herself before she gets married.

[B]

Yeah, that's why I'm a big old fan of no one gets married till 28. You know these couples that start dating in high school. I know the romantic notion that we met in elementary school and then we dated all through high school. Sounds so sweet. It's the dream. And then college, we were with each other and he's the only guy I've ever been with, or she's the only woman I've ever been with. But you can't help but wonder. I think it would be human nature to wonder, what else is it?

[D]

Like, some people can make it work. Some people have zero desire to explore or they have zero curiosity. I went to college, one of my sorority sisters was like this. Like, she had zero rebel bone in her body. Like, just didn't have that desire whatsoever at all. And she was with her high school boyfriend. They dated all through college. They're married now, they live in Florida. They've got two kids. Like everything is hunky dory. But she's just never had that curiosity. You know, Some people are just built differently. But if you've got the, like the last caller, like if she's got the curiosity now to seek it out just before, you know, she's in get, you know, she gets married or whatever, like that's in her.

[F]

Right?

[D]

Like that.

[B]

I don't know.

[C]

I just think she's saying it wasn't just curiosity. She went through with it.

[D]

Right, right.

[C]

You know.

[D]

Right. And that curiosity is gonna peek its head again, you know.

[B]

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

[F]

Hi.

[B]

Hey. You're on the Voice Disguiser.

[F]

Yeah, I'm actually. I started it back in September. I reconnected with an old boyfriend and have kind of been having a kinda. Yeah, kinda. Well, we have slept together since reconnecting. I've been married to my husband be three years in May and in August, actually, I filed for divorce from my husband because things were just. I mean, I just. Every time I looked at him, I want to hit him in the face with a frying pan.

[D]

Okay, that's a good indication.

[B]

That got to a pretty bad point. Okay. Very Southern.

[C]

That's right.

[F]

And so I, you know, I reconnected with this old boyfriend. And honestly, ever since I reconnected with. With him, my relationship with my husband has been so much better.

[B]

Really? So you stayed with your husband because of your affair?

[F]

Well, at first I stayed because I was guilty. I Felt really guilty that I, you know, had done something like this. And then

[B]

you got over.

[C]

Are you still with the guy?

[D]

You're.

[C]

You know, the Mr. Or whatever you call a guy on the side.

[B]

Mastrous.

[C]

Are you still with him?

[F]

In a way? Yeah.

[C]

Kind of. Sort of. If you're sleeping with him, you're with him.

[B]

I know there's a lot of great. Either yes or no. Are you still sleeping?

[D]

This might be the first time she said it out loud.

[B]

Yeah. Are you sleeping with the guy still?

[F]

No.

[D]

So no. Come on. It's not just a no.

[B]

So you guys are communicating with each other, but there's nothing physical in there.

[C]

There's several ways to be intimate with each other. Are you being intimate with him in any way?

[F]

No.

[B]

No. Okay. All right. But it helped for a while.

[F]

It did. Yeah. And I don't know if it was the. The guilt factor that I could do that or.

[B]

Why are you shaking your head?

[C]

Because this one doesn't qualify. She is sleeping around on her husband with this guy, and she's staying with her husband.

[D]

But she didn't follow that story at all. She filed for divorce, and then she got with the high school guy. She got back with the husband because of the relationship with the high school guy?

[C]

Yes. She's doing both.

[F]

Confused.

[B]

I'm gonna take one more call, then we'll move on. We gotta talk about you. Hey, Laurie. Good morning. You're on Q100.

[E]

Good morning. How are you?

[B]

Okay. How are you?

[E]

I'm doing really well. I'm kind of torn with this because I grew up in a very, very religious home. My dad was a minister. You don't have sex, so you get married, all that stuff. And I waited. I. But it was back where. I'm 44, so it's back where it's. Everybody got married at 20 and 19, things like that. And I did. And I married my first, my one of my only. And I wasn't his first. But he ended up cheating. He's use the excuse of only being 19. But I always had that curiosity in my head, you know, what would it be like with somebody else?

[B]

I think that's human nature.

[E]

Yeah, it is human nature. And once we finally did get divorced, because I just. I couldn't get over it. I only found out because they were both my best friends. But I kind of went wild for a year. And I think that, you know, it's not so much cheating, but I think if you get back in the relationship after you've cheated without telling the other person, there's always going to be that negativity there that I don't know that you can have a full 100% relationship with somebody based on a lie.

[B]

So no matter what, if you cheat, you got to come clean. Would be your advice.

[E]

Yes.

[B]

Okay. Thank you for calling. I would. I would have always had that curiosity. Also, I could have never been one that just dated one woman my entire life. There's just no way. I wish I could have been, but actually, I don't.

[D]

You don't wish you could have been? No. Got it. Okay. I understand what you're saying.

[C]

Yeah.

[B]

Because it sounds like it's like the dream to be with just one. But that wouldn't have been my dream.

[D]

It's like the purity.

[E]

Yeah.

[D]

Of the whole thing.

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