Vault: Should you confess your cheating past to your spouse?

Summary

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The Bert Show Episode Summary

Episode Title: Vault: Should you confess your cheating past to your spouse?
Date: May 27, 2026
Main Cast: Bert (Host), Amy, multiple guest commentators and callers

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Overview

This episode dives into a candid and sometimes heated conversation around the question: If you have a history of cheating in a previous relationship, should you disclose it to your new partner, especially if marriage is on the horizon? Using a listener's heartfelt email as a launch point, the team, callers, and guest commentators debate trust, transparency, personal growth, and whether “once a cheater, always a cheater” is ever true.

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Key Discussion Points & Insights

1. The Email Dilemma (01:30–02:42)

• Listener Email:
  A listener who cheated during a previous marriage (with multiple partners) admits deep regret and asks if they must reveal this to their new, serious partner:

  “It’s not a day that goes by I don’t think about my infidelity. I was just wrong... I’ve met somebody new and we’ve fallen in love... Do I have to confess my infidelity?” (01:30-02:42)

2. Should You Disclose Past Infidelity? (02:42–05:43)

• Guest Commentator 1 suggests context matters:

  “If it was a relationship specific infidelity issue then I just don’t know if he has to. I guess eventually the conversation would come up.” (02:42-02:57)

• Group Debates Full Disclosure: Several agree openness can build trust, while others express skepticism that a cheater can ever truly reassure a partner.

  “Full disclosure is good because... it would make you almost closer to know about each other.” —Guest Commentator 2 (03:16-03:38)
  Bert is skeptical:
  "You would never be able to convince me that there is 0% chance it can happen again." (04:40-05:01)

• Amy questions whether the past shapes the present, noting:

  "It is a building block in the current way you view relationships... Past is in the past, and you’ve learned a terrible lesson..." (04:15-04:40)

• Consensus: The panel notes that queries about past relationships are common and lying (i.e., omitting the truth) could be problematic longer term.

3. How Long Does the Past Linger? (05:43–06:20)

• If the relationship is serious and heading toward marriage, all agree honesty becomes more necessary—but timing and context are crucial.

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Notable Caller Stories & On-Air Perspectives

Amy (Caller): Hidden Cheating, Decades Later (06:20–09:18)

• Married 20+ years, only recently learned her husband cheated in his previous marriage.
• Impact:

  “It would have definitely been a deal breaker 20 years ago... I have serious, serious doubts about what was going on in the beginning of the marriage.” (06:46-07:57)

• She now views earlier years with suspicion, despite no recent trust issues.

Sue (Caller): Betrayed by a Serial Cheater (09:31–11:41)

• Sue got pregnant by a married man who then left her for someone else. She declares,

  “Once a cheater, always a cheater. I will never again date another guy that has cheated.” (09:33-10:34)

• Bert and Amy point out her own role in cheating:

  "Aren’t you a cheater also?" —Bert (10:48-10:58)
  “Technically, yes, you are.” —Amy (10:56-10:57)

• Sue admits, “Everybody makes mistakes,” showing the double standards at play.

John (Caller): When a Spouse Comes Clean (11:48–12:54)

• John’s wife confessed to cheating, and while hurt, he values her honesty:

  “I’m actually happy that she told me now... now I know what kind of person she is.” (12:32-12:54)

• Reveals immediate pain but long-term clarity.

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Big Ideas & Arguments

1. Is honesty always best?

• Disclosure advocates (full honesty builds trust, ‘the truth will come out’).
• Keep it to yourself brigade (the past is the past—don’t relive or rehash if you’ve truly changed).

2. Once a cheater, always a cheater?

• Some panelists and callers (like Sue) firmly believe in this adage.
• Others (Bert, Joe) push back, suggesting circumstances matter and people can change.

3. When and how to have the conversation?

• Early honesty is easier, but the longer the relationship, the harder (and potentially riskier) the disclosure.

---

Memorable Quotes & Moments

• Bert:

  "If I’m dating you and I know you’re divorced... I’m gonna ask you, so what happened in the relationship?" (05:04)

• Amy (Responding to past secrets):

  “But if I did find out from someone else about my own spouse, then I would think that there would be issues there.” (04:07)

• Sue (Caller, on learning her mistake):

  “I should have known, you know, if he’s cheating on his wife, he was gonna cheat on me.” (09:46-10:34)

• Bert (To Sue, on hypocrisy):

  "So then the guy that you're with right now, this great guy, should never trust you for the rest of your relationship, correct? Based on what you said in the beginning of the phone call." (10:56-11:08)

• Joe (Caller, on cheating being context-driven):

  “It’s not once a cheater, always a cheater... certain people invoke cheating given however the relationship’s going.” (14:27-14:53)

---

Important Timestamps

• 01:30: Email sets up the theme: Must you disclose a cheating past?
• 02:42: Roundtable opens debate on honesty versus privacy.
• 04:40: Bert strongly asserts he’d never fully trust someone with a known cheating past.
• 06:20: Amy (Caller) shares the effect of discovering a secret decades later.
• 09:31: Sue shares how being involved with a cheater reshaped her outlook.
• 11:48: John (Caller) offers perspective on the immediate aftermath of a confession.
• 14:27: Joe challenges the “once a cheater, always a cheater” myth.

---

Final Thoughts

The Bert Show’s authentic, conversational style lets listeners hear real struggles and opinions around the moral and practical questions of honesty in relationships. There’s no universal consensus—everyone’s line is different. The ultimate takeaways:

• Past actions do shape present perceptions—both yours, and your partner’s.
• Trust requires some risk, but lies or omissions can corrode even the best intentions.
• People can change, but the shadow of past mistakes lingers, and openness might be the only way to truly move forward.
• If you’re keeping a secret, ask yourself whether you’d be okay if your partner found out from someone else.

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For listeners seeking to make sense of their own relationship histories or whether to reveal them, this episode is a relatable, revealing, and sometimes uncomfortable exploration of honesty, trust, and human fallibility.

Transcript

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[Bert (Host)]

You're on the Burt Show. All right. The email reads like this. We've done a pretty good job. By the way, hats off today about staying away from Tiger. Congratulations, y'.

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All.

[Bert (Host)]

Yes, I'm gonna change that. Okay. Hey, Bert, I've been listening to the. I've been listening this past week to all the Tiger woods talk, and you've really made me think about something. I got divorced two years ago. I was married for five years and the relationship dissolved because I cheated. Not with just one person, but with a few others. There are always reasons that lead up to something like this, but I accept full responsibility. I should have handled the relationship differently. It's not a day that goes by I don't think about my infidelity. I was just wrong. Anyway, I've met somebody new and we've fallen in love. I know it's only a matter of time before we are engaged and spend the rest of our lives together. No.

[Amy]

Such a romantic story.

[Bert (Host)]

We can pause there. Do I have to confess my infidelity? Is this something about my past that really needs to be relived? I honestly believe I'm capable of being monogamous with the right person. I feel like a different person now. So do I really need to disclose my cheating past?

[Guest Commentator 1]

The first thought out of my head is that if it was a relationship specific infidelity issue then I just don't. I don't know if he has to. But I guess eventually the conversation would come up. But how long have they been dating?

[Bert (Host)]

It doesn't say she just. Or this person just.

[Guest Commentator 1]

Because it doesn't sound like he was a player and he was just cheating on everybody he'd been with.

[Bert (Host)]

And I think it's funny how you keep saying he.

[Amy]

Yeah. Is it a guy or a girl?

[Guest Commentator 1]

Oh, I'm sorry.

[Bert (Host)]

It doesn't say.

[Guest Commentator 1]

Okay. Sorry.

[Bert (Host)]

It just says they've met somebody new, fallen in love. Only a matter of time before we are engaged.

[Guest Commentator 1]

I think I thought he. Because of the tiger reference.

[Guest Commentator 2]

I think if you're gonna marry somebody though, don't you want full disclosure about everything that they did before? I mean because you think that you're different anyway right? Because you're marrying them. So I think full disclosure is good because I think it kind of. I don't know, I think it would make you almost like closer to know about each other. And your, you know, that is gonna

[Bert (Host)]

be a deal breaker though for some. 404-741-Q100 like, I know some people think once a cheater always a cheater. So if you confess to the infidelity in a marriage and. And I'm about to get married to you, how do I know that there won't be circumstances that will lead you that I already know that you're capable of it because you've already done it. But the past is the past.

[Guest Commentator 3]

I don't know if I'd want to know. I mean it's a brand new. It's a brand new relationship. You didn't cheat in this relationship.

[Amy]

Doesn't matter.

[Guest Commentator 1]

But if I pass. But if I did find out from someone else about my own spouse then I would think that that would. There would be issues there.

[Amy]

It's the past of the past is. Yeah. But it is a building block in the current way you view relationships. So it could be a good thing or bad thing. It could be the past is in the past, and you've learned a terrible lesson, and there's a zero chance it'll happen again. But it depends on the person you're telling. But I think you do have an

[Bert (Host)]

obligation to explain that you would never be able to convince me if you have infidelity in your background. Then if I'm dating you, you would never be able to convince me that there is 0% chance it can happen again. If you went through a relationship and you didn't have the infidelity, I could believe it. But if you've already done it and I'm dating you, I can never believe that that's true.

[Guest Commentator 2]

So you wouldn't want to know.

[Bert (Host)]

I don't know how it. I don't know how it couldn't come up. Like, if I'm dating you and I know you're divorced at some point or another, I'm gonna ask you, so what happened in the relationship?

[Guest Commentator 2]

Right.

[Bert (Host)]

Which I'm assuming this person has already

[Amy]

lied, but that could be. Oh, we drifted apart. We became two different people. Yeah, we got married too young. Work, you know, work. I had to travel for work. Blah, blah, blah. You could come up with a million different.

[Guest Commentator 2]

Because I think full disclosure can build trust, regardless of your mistakes in the past.

[Guest Commentator 3]

Depending on when. How long they've been dating, though, if it's like the beginning of the relationship. Yeah, full disclosure. But depending on if it's like six months in and you've already built the trust up and then exposing the past.

[Bert (Host)]

I'm too late. Yeah, too late. They must have been dating a nice amount of time here, because this person says they've fallen in love. Although some people fall in love in 24 hours, I know it's only a matter of time before we're engaged and spend the rest of our lives together, which makes me feel like they've been going out with each other for a good long time.

[Guest Commentator 1]

It just depends on the person. I mean, I think, again, it's. It's not. The mistake itself is what you do with it and how you handle it. And if you truly are sorry and you truly, you know, have changed your ways, then you're. I mean, if you're committed to it, then you're. I mean, you're a person of your word. You know, it just. It depends on that. That listener, you know?

[Bert (Host)]

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

[Sue (Caller)]

Can I have the voice discussor?

[Bert (Host)]

It's Always good to ask before you go on the air there, though.

[Amy]

Just for future reference, do you need a different name? Amy?

[Joe (Caller)]

No.

[Amy]

Okay.

[Bert (Host)]

How are you?

[Amy (Caller)]

I'm good.

[Bert (Host)]

You're on the voice disguise right now.

[Amy (Caller)]

Okay. Well, I've been married 20 something years, and I found out a couple weeks ago from my stepson why his dad and his mom got divorced.

[Guest Commentator 2]

Mm.

[Amy (Caller)]

And it was because he cheated. And that would have definitely been a deal breaker 20 years ago.

[Bert (Host)]

And you just found out about this now?

[Joe (Caller)]

Yeah.

[Bert (Host)]

Wow.

[Guest Commentator 2]

Did you bring it up to him yet?

[Amy (Caller)]

No.

[Guest Commentator 1]

Why not?

[Amy (Caller)]

What's the point?

[Guest Commentator 1]

Is it a deal breaker now.

[Amy (Caller)]

After 20 years? I don't. I mean, I got a couple kids and he's the breadwinner, so, you know, now there's really not. No, it's not gonna be a deal breaker now.

[Bert (Host)]

But it would have been back then.

[Amy (Caller)]

Yeah. Never. Never would have married him.

[Bert (Host)]

Do you trust him less today, knowing that even though he hasn't done anything over the last 20 years, do you trust him less today?

[Amy (Caller)]

Oh, well, not less today because, I mean, we're. We're older and stuff, but now looking back at all the late nights and going out with the boys and all that that happened the younger, you know, in the earlier years.

[John (Caller)]

Mm.

[Amy (Caller)]

Oh, yeah. Now I have serious, serious doubts about what was going on in the beginning of the marriage because I think the

[Guest Commentator 1]

theory about once a cheater, always a cheaters, that idea that the person doesn't. Didn't have the boundaries to stay monogamous. And so the thought is, well, if they don't have the bound, the. It's with that within that person, they don't have boundaries with one. They're not going to have boundaries with anybody. Yeah. You know. You know, it just depends, guys. Depends on the circumstance, I guess.

[Bert (Host)]

See, like, I don't know what the argument here is, Amy, because what you're saying is, had you found out about this 20 years ago, you would have never married him. But the truth is, you've been married to this guy for 20 years, and it's obviously worked out okay.

[Amy (Caller)]

Well, yeah, I guess, because I probably. Well, I wasn't aware of it, so I wasn't, like, looking for it.

[Bert (Host)]

But you. But you've been in a successful marriage for 20 years that you would have never given a chance had he told you why his previous relationship broke up.

[Amy (Caller)]

Yeah, successful. I would use that term loosely, whether it's actually successful or not. But I mean, it stayed together because of the kids and, you know, finances and things like that. I mean, it Was a matter of nowhere else to go.

[Guest Commentator 2]

Yeah, to me it sounds like she's not in a real happy place and this is now an excuse to get out. Well, if you would have told me 20 years ago, I would have never done it. So I'm allowed to get out the door now.

[Bert (Host)]

You know what I mean?

[Guest Commentator 2]

She was looking for a reason.

[Bert (Host)]

Here's Sue. Good Morning. You're on Q100.

[Sue (Caller)]

Hi. I just wanted to justify that I feel that once a cheater, always a cheater. Last year, I actually got pregnant by a man.

[Guest Commentator 2]

A what?

[Sue (Caller)]

A married man. I got pregnant by a married man.

[Bert (Host)]

Okay.

[Sue (Caller)]

And two months later, he broke up with me for me to find out that he'd been lying to me the whole time, along with his brother and his sister in law.

[Guest Commentator 1]

You didn't know he was married?

[Sue (Caller)]

No, no, no, I knew he was married, but that was definitely a mistake on my part. I should have known, you know, if he's cheating on his wife, he was gonna cheat on me, but he actually broke up with me two months later. Then I think I was about like, what, four months? I guess about four months pregnant. And he left me, married another girl. After he divorced his wife, married another girl and adopted her baby. And I've yet to speak to him about my child.

[Amy]

And that brings us to the answer to the question, would you get into. Would it be a deal breaker for you if you found out the person you were in a relationship with had cheated in the past?

[Sue (Caller)]

Oh, I will never again date another guy that has cheated.

[Bert (Host)]

But listen to what you're saying.

[Sue (Caller)]

The guy I'm with now, which is a wonderful guy, you know, he's raising my.

[Bert (Host)]

Stop, stop, stop, stop me.

[Sue (Caller)]

When I was five months pregnant, maybe the guy just. I gave him 21 questions about his past.

[Bert (Host)]

Sue, listen to yourself, though, because you said, once a cheater, always a cheater. Aren't you a cheater also?

[Amy (Caller)]

Technically, yes, you are.

[Sue (Caller)]

Right.

[Bert (Host)]

Okay, so. So then the guy that you're with right now, this great guy, should never trust you for the rest of your relationship, correct? Based on what you said in the beginning of the relay, the beginning of

[Sue (Caller)]

the phone call, yeah, you could possibly be right.

[Amy (Caller)]

But everybody makes mistakes.

[Amy]

Hey, sue, do you know that the. The guy that was cheating on you, do you know that they actually had a physical relationship or did he just want some peace and quiet?

[Bert (Host)]

Oh, no, no, no.

[Sue (Caller)]

They actually. She was. Actually, they were both. They weren't separated, but like, they were married eight years and six of which he lived in the basement.

[Guest Commentator 1]

Honey, I honestly, I don't care. Because you lost all legitimacy when you talked about. Okay, this married man that I was seeing.

[Sue (Caller)]

What?

[Bert (Host)]

But she just said that she's not trustworthy either is really what she just said.

[John (Caller)]

Right?

[Guest Commentator 1]

Yeah, she would admit it, but that's the truth. I think everybody makes mistakes when it's my mistake, Bird. But everybody else wants to cheater. I was a cheater.

[Guest Commentator 2]

Right.

[Bert (Host)]

Here is John. And you're on the voice disguiser. Good morning.

[Amy]

Hello.

[Bert (Host)]

Hey, John, you're on the voice disguiser.

[John (Caller)]

Hey, how you doing?

[Bert (Host)]

Good, thank you.

[John (Caller)]

Okay. I mean, I'm not doing really good, but actually on Friday, I found out that my wife cheering me, we were having dinner and then she started crying and she came up saying that, oh, no, it's Christmas and I cannot keep this any longer. And she told me that cheated on me twice.

[Bert (Host)]

And how long ago did this happen?

[John (Caller)]

What do you mean, how long?

[Bert (Host)]

How long ago did she cheat on you?

[John (Caller)]

Oh, she didn't tell me. I just know that she did.

[Amy]

Oh, you didn't have any follow up questions for that?

[John (Caller)]

No, me on Friday, she just started crying and then she told me. And you sucked because I know the two guys that she did it with. But I'm actually happy. I'm actually happy and I appreciate that she told me because now I know what kind of person she is. And I'm actually really happy that she told me now. I mean, I wasn't there for more longer and then, you know, you'll be bored.

[Joe (Caller)]

It's not that.

[John (Caller)]

It's Christmas, dog, and I'm gonna be like, you know, thinking about it all day.

[Amy]

But so what country is he from?

[Bert (Host)]

Bert, I don't want to get into a little off topic here. The question was from the email is, does she tell this new guy or does he tell this new girl that he's seen that the reason why his marriage dissolved was because he or she was. He was screwing around or she was screwing around. Good morning, Brittany. You're on Q100.

[Sue (Caller)]

I don't think it's necessary to tell everything from the past. I think past should stay in the past. And quite frankly, what man is going to tell that they've cheated in the past?

[Bert (Host)]

Well, you can say the same thing

[Joe (Caller)]

about a woman or a woman.

[Guest Commentator 3]

And I tend to agree with that, just depending on how far in the relationship you are. I mean, if that's honest, like right off the bat, then. But if you're six months in, I wouldn't want to know.

[Amy]

But how do you bring it up? Right off the bat. Like, it's weird in talking. It's weird in both places. But at some point when you have the conversation about going to the next level, then you gotta have the.

[Bert (Host)]

Well, I think you probably justify it in your head and you won't bring it up because there were unique circumstances to that relationship that I think you probably feel that pushed you into that infidelity, whereas you wouldn't disclose all that.

[Guest Commentator 1]

I just think that you have to check yourself.

[Amy]

I mean, you can't before you wreck yourself.

[Guest Commentator 1]

That's right. Before you get into another marriage, if you were going to marry the person and you are the cheater, then you've got to make sure that you're not going to make that same mistake with your new spouse.

[Bert (Host)]

Just real quick here.

[Guest Commentator 1]

Have to do that.

[Bert (Host)]

Joe, I got about 15 seconds. What you got, man?

[Joe (Caller)]

I just wanted to say that it's not. Once a cheater, always a cheater. I've died. Who's cheated before? It's certain people invoke cheating. Given however the relationship's going.

[Amy]

Certain people invoke cheating in a certain way.

[Joe (Caller)]

Some. Yeah. In a relationship. Some people will always be cheated on. And there's people who will always have a faithful partner who.

[Bert (Host)]

Who always gets cheated on.

[Joe (Caller)]

I. Whether or not they are confident. There's certain aspects of a relationship that bring out cheating on another person. I mean, I've cheated. I've had relationships where I've cheated way more than one should. And I've had relationships where I was completely faithful.

[Bert (Host)]

And you put this on the women that you're with and not you.

[Joe (Caller)]

I don't know. Not. I'm not gonna be that foolish. No, I definitely know that I'm to blame in lots of. Lots of areas, but at the same time, there's. It's kind of go back and forth.

[Amy]

So what he's saying is there's a hypocritical day.

[Bert (Host)]

Does someone check the calendar?

[Amy]

Well, what he's saying is there's. He wouldn't bring it up to certain people. And if he's in a relationship and the new girl that he's dating isn't the type that he would cheat on, no reason for him to bring it up because it's a non issue anyways.

[Bert (Host)]

Well, the girl he first started dating, dating in the beginning wasn't the kind of girl he cheated on either.

[Amy]

Why you got to bring up details?

[Bert (Host)]

Right? Listen, it's the Vert show.

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