Vault: Would You Ever Date A Cheater?

Summary

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Podcast Summary: The Bert Show

Episode Title: Vault: Would You Ever Date A Cheater?
Date: January 8, 2026
Host: Pionaire Podcasting (Bert, Kristin, Abby, Cassie, Tommy & The Bert Show Cast)

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Overview

This episode of The Bert Show dives deep into the provocative question: "Would you ever date a cheater?" Using a storyline from "Desperate Housewives" as a springboard, the hosts and callers explore trust within relationships that started with infidelity. The discussion centers on whether trust can ever be fully restored once broken and what it's like to be "the other woman"—and then become the primary partner. Throughout, real callers share their raw, personal experiences, generating candid, sometimes heartbreaking, and often thought-provoking moments.

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Key Discussion Points & Insights

1. TV Inspiration: Desperate Housewives as Catalyst (01:48 – 03:59)

• The episode opens with a recap of a "Desperate Housewives" plot, where Lynette discovers her husband Tom began their own relationship by cheating on his ex, Annabelle. Lynette finds out Tom rehired Annabelle without telling her for three months, leading to trust issues.

• The hosts play and dissect a heated clip between Lynette and Tom, fueling the core episode question about trust after infidelity in relationships.

  Key Quote:

  “Are you so insecure that you have to pull that crap?... Anyone is capable of anything. The first time we ever met, you were cheating with you. Cheating with you. It's a pattern of behavior.” – Lynette, TV Clip (03:22)

2. The Trust Issue: Can You Ever Fully Trust Again? (03:59 – 06:18)

• The team discusses whether, after infidelity, it's possible to ever trust a partner 100% again, especially if you started as "the other woman."

• Host Bert notes that prior callers overwhelmingly say trust was never quite fully restored, even if relationships continued.

  Key Quote:

  “If he's just late, you know, by 30 seconds, I start thinking, okay, who's he screwing around with? So the trust was never quite restored.” – Bert (03:59)

• Question posed: If you started out as the 'other woman,' do you ever fully trust the person—or do you suspect a pattern?

3. Callers Share Their Experiences (06:45 – 19:32)

a) Maryanne: The Lingering Distrust (06:47 – 07:17)

• Maryanne shares her experience: three years into a relationship that started when he was with someone else, she admits ongoing trust problems, always fearing he’ll cheat again.

  Key Quote:

  “We always have, like, problems in our relationship just because of that, because I know that he did that, and he probably will do it again.” – Maryanne (07:12)

b) Anna: The Paranoia Never Quite Goes Away (07:27 – 08:22)

• Anna describes similar doubts: “If he left somebody else for you, he could always leave you for somebody else.”
• The hosts probe whether Anna also struggles with guilt or trust as "the other woman." Anna is candid: “It’s hard... I’m not that special that he might not up and leave me one day.”

c) Callers and Hosts on Attraction vs. Action (09:05 – 10:26)

• Anna brings up whether cheating is "hereditary," referencing outside radio chatter.
• The hosts debate free will:
  • Some argue you can’t help who you’re attracted to, but you can decide your actions.
  • “You control who you’re attracted to and who you’re not... that’s what it’s about.” – Host (10:02)

d) Sally: Ongoing Insecurity and Regret (10:26 – 15:18)

• Sally tells a detailed, emotional story: she got into a relationship without knowing the guy had a girlfriend (“I had no clue he had a girlfriend...”), later learned the truth, but stayed.
• Two and a half years later: she’s plagued by mistrust, especially with long-distance logistics.
• Sally strongly warns other women:
  Key Quote:

  “I advise every girl out there that is in a situation to get out of it as soon as possible because you never get over it and it puts you through hell... it’s always going to be in the back of your mind.” – Sally (12:20)

e) The Hosts Offer Tough-Love Advice (13:01 – 16:21)

• The hosts tell Sally: If you have no trust, why stay? "Just leave," they repeatedly urge.

• Sally struggles, explaining her isolation and lack of friends. The hosts note that obsessive relationships can cause further social isolation.

• Emotional low point: Sally reveals exhaustion and a wish to forget her boyfriend entirely.

  Key Quote:

  “I want something to happen. I want to, like, be put in a coma or something just so I can forget this guy ever existed in my life.” – Sally (16:21)

  • The hosts respond with empathy and encouragement, highlighting the universality of heartbreak and the necessity of learning from hard experiences.

f) Jackie: “I Trusted Him—But I Was Stupid” (18:03 – 19:38)

• Jackie recounts her story: her partner left his wife for her; they had eight years of marriage, divorced, and he remarried his first wife two days after.

• Jackie reflects: she unreservedly trusted him and regretted it, signaling that patterns can—and do—repeat.

  Key Quote:

  “Because I was stupid. I mean, I was just absolutely stupid. And then we ended... and on the 62nd day, he remarried the woman that he was with, and he met me.” – Jackie (18:14)

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Notable Quotes & Memorable Moments

• “Everyone is capable of anything.” – Lynette, from "Desperate Housewives" clip (03:24)
• “If he's just late, you know, by 30 seconds, I start thinking, okay, who's he screwing around with?” – Host (Bert) (03:59)
• “If he left somebody else for you, he could always leave you for somebody else.” – Anna (07:48)
• “I advise every girl out there that is in a situation to get out of it as soon as possible because you never get over it and it puts you through hell.” – Sally (12:20)
• “He doesn’t have any respect for you because you’re not respecting yourself.” – Host, to Sally (15:49)
• “I trusted him, but I shouldn’t have.” – Jackie (19:32)

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Timestamps for Key Segments

• 01:48 – 03:59: Desperate Housewives recap and opening roundtable on trust and infidelity
• 06:47 – 07:17: Maryanne’s story (persistent distrust)
• 07:27 – 08:22: Anna’s story (trust issues and mutual suspicion)
• 10:26 – 15:18: Sally’s story (regret, mistrust, and host advice)
• 18:03 – 19:38: Jackie’s story (cycle repeats, post-divorce regret)

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Tone & Takeaways

The episode maintains The Bert Show’s signature blend of authenticity, humor, and empathy. The tone is conversational yet deeply compassionate, especially when callers share emotional struggles. The hosts challenge, encourage, and offer practical advice—but always in a way that’s relatable and non-judgmental. Listeners are left with the sobering but empowering message: if a relationship begins with betrayal, regaining full trust is rare, and self-respect should never be sacrificed for companionship.

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For listeners who haven’t tuned in:

• You’ll gain insight into the emotional aftermath of dating “a cheater,” hear honest advice from both hosts and callers, and witness the turmoil and hope interwoven in real-life stories of love, regret, and moving on.
• The episode stands as both a cautionary tale and a supportive conversation for anyone questioning the foundations of their relationship—or weighing the risk of trusting after betrayal.

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Transcript

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[C]

The Birch show the Birch show so Desperate Housewives this weekend. Oh, that was a good one. Sunday was a really good one.

[E]

Every single show is a good one. It's my only appointment television. I love Desperate Housewives.

[C]

It seems like in this episode, like every storyline, we got some nugget of information out that we didn't know before, you know, and the storyline with Lynette and her husband Tom, I thought was a really interesting one. A really interesting one with a lot of interesting questions involved in it also.

[E]

Well, we found out this last episode that Tom started dating Lynette when he was cheating on his girlfriend Annabelle. So Tom and this woman Annabelle are dating. He cheats on Annabelle with Lynette, ends up marrying Lynette. Now, so far, we don't know. We don't know about any infidelity. Lynette knows about no infidelity with her husband Tom. But she finds out in this episode that Tom has just rehired Annabelle at his company and did not tell Lynette about it for three months. So in Lynette's little diabolical plan is, you know, the whole cliche of keep your friends close but keep your enemies closer. She invites Annabelle over for dinner, and.

[C]

Then she starts doing all sorts of ridiculous things to prove to the ex girlfriend that their marriage is really, really strong. And her husband is like, this is the stupidest thing I've ever.

[F]

Quite a show you put on tonight.

[C]

Show the boys paintings, all those references.

[F]

To how happy we are. What's wrong with subtly reminding Annabelle that you're happily married?

[C]

Because it wasn't subtle, and it's an insult to me.

[F]

I did not mean it that way.

[C]

Are you so insecure that you have to pull that crap?

[F]

Keep your voice down. It doesn't matter if she has feelings for me as long as I am not interested. Have I ever, ever given you any reason to doubt me? Anyone is capable of anything. The first time we ever met, you were cheating with you. Cheating with you. It's a pattern of behavior. Oh, give me a break. Well, what am I supposed to do? You hire your old girlfriend and you don't tell me about it for three months. I could have told you from day one, and you would still be jumping down my throat.

[C]

No, Annabelle is ancient history.

[E]

She's in the next room.

[C]

How long do we have to be married, Lynette?

[F]

How long until you actually trust me?

[C]

So here's the question I want to ask women here, because we've asked the question before in relationships that if your husband or your boyfriend ever screwed around on you, did you ever fully, 100% trust him again? And you guys called up, and you, I mean, have said like 100% of you said never. Quite entirely. Like, we might have gotten back together again. Our marriage survived, and things are okay, and things are actually great. But if he's Just late, you know, by 30 seconds, I start thinking, okay, who's he screwing around with? So the trust was never quite restored. So here's the question, in listening to that clip that I have for you women, is that if at one point you used to be the other woman, so he was dating somebody else, saw you, was overwhelmed, and then started a relationship with you while he was still dating or married to somebody else, and then ended up dumping the current girlfriend for you, so you were the other woman. And things have worked out really well with you guys. Do you trust him 100% in your relationship? Because as Lynette says here, he's shown a pattern of infidelity. So do you ever fully, fully trust the guy you know?

[G]

Or were you just so special that it was destiny and then you were meant to be together despite the fact that someone else was there?

[C]

Because here he's saying, I will, in your eyes, I will always be guilty of infidelity, even though you're the one I screwed around on. Now I think if I'm him, I'm with. Yeah, I think if I'm him, it's pretty easy to turn it around. Also, because is she trustworthy?

[G]

She's the mistress. Yeah. She knew what she was getting into, too.

[C]

So she ended up screwing around with a guy that was in a relationship also, so he could say the exact same thing. So how would you answer that?

[E]

I don't know. That's hard to tell, because you can't really blame somebody for something that they haven't done in your relationship. You know, you can't blame him for infidelity or be suspicious of activity that's never happened. But I wonder if that would always be nagging in your mind.

[C]

It would have to be. It's always gotta be there.

[G]

Cause to me, it's like a. Some people would look at that as his character. If he, you know, if he cheated before, if it didn't mean much to him before, even if it was me or not me, then it's a character flaw in him.

[E]

I have thought about it in relationship to Britney Spears and Kevin Federline. Cause, you know, Kevin wasn't married to his children's mother, Char Jackson. They were just dating. But she was pregnant with his second child when he left her for Britney Spears. So I wonder, now that Britney's pregnant, does she, in the back of her mind, consistently worry that Kevin Federline's gonna leave her while she's pregnant? Because you know what?

[C]

He did it before. That's a great question. Hey, Maryanne.

[F]

Hi.

[C]

Good morning.

[F]

Good morning.

[C]

What's up?

[F]

Nothing. I have a story of my own about this. My boyfriend of three years, we met when he was dating somebody else, and I never thought we were going to end up together. I just thought, you know, he's really cute, so. And I knew about it. I knew about his girlfriend, and she moved away for a little while. He said he was going to wait for her, but we ended up dating. And we're together till this day. But we always have, like, problems in our relationship just because of that, because I know that he did that, and he probably will do it again.

[C]

So even though you're the one he left her for, it doesn't matter. There's still distrust there. That pattern of behavior that what's her.

[F]

Face is talking about.

[C]

Lynette. Mm. Thank you.

[B]

Good morning.

[C]

Anna, you're on all the hits q100.

[F]

Good morning. I wanted to let you guys know I had met a guy, and he left the other woman for me, and we're happily together, just like your last caller. But you always have a little, you know, if he's out or whatever, you always kind of wonder, because if he left somebody else for you, he could always leave you for somebody else.

[G]

Now do you think? I mean, because I. And I want to ask you, since you were the other woman, you feel like you're not as guilty as him because you weren't with somebody, even though you were the mistress and knew what you were doing.

[E]

Like, why.

[G]

Why should he trust you, too?

[F]

Oh, and we've talked about it, you know, and I'm like, well, we each have our own issues, and if you can put yours aside, I can put mine aside. It's hard. It's hard. But, you know, I'm not that special that he might not up and leave me one day. You know? I mean, she thought she was pretty special, too, and then he left her. So you just never know. It's always kind of in the back of your mind.

[E]

Because to me, it's not necessarily a pattern of behavior, of cheating as it is being really attracted to something new. There's two levels there, you know, because you were the new thing. It was like, new and fresh and exciting, and he was so overwhelmed by that new, fresh, exciting thing that he took off and went to it. So then once you become kind of old, you know, old news, not as new, not as fresh, not as exciting or whatever, and a little bit more comfortable, a little bit more routine, is he gonna be attracted enough to the new, fresh, exciting thing to go Le.

[F]

You for it keeps you on your toes. Definitely.

[C]

That's good. That's the way healthy relationships should be. Everybody should be on edge.

[E]

Everybody should be paranoid, nervous all the time.

[C]

So what does it say about you, though? I mean, what.

[F]

I don't know. I've struggled with that. It kind of goes back to the whole, you know, I've talked about it with my older sister, and, you know, she brings up the whole thing that I think Geller had on his show the other day is cheating kind of a hereditary thing. And that's a whole nother thing. You guys probably don't even want to open up on your show, but.

[D]

It.

[F]

Causes you to step back and look at yourself and, you know, yeah, I knew about the other woman. And, you know, I mean, I know other women feel like I do. Sometimes you just can't help it.

[C]

I don't buy that. What do you mean? Sometimes you just can't help it?

[F]

Well, he wasn't married. I mean, he was seeing someone else, and they were having some problems. And, you know, yeah, maybe I shouldn't have been as attracted to him as I was. But I mean, what I'm saying is when you know you're attracted to somebody and you just. You can't help it, you give in.

[E]

To that is what you did, is you gave in. You can definitely control it. I mean, married people do it all the time. You control who you're attracted to and who you're not. You know, I mean, that's what it's about.

[C]

And I don't think you can control that. I don't think you can control who you're attracted to. I think you make a decision on how you're gonna handle it.

[E]

Exact what, you know, whether you give in to those urges or not is what you can control.

[C]

Hey, Sally, you're on all the hits Q100.

[F]

Honey. Be a little realistic. Obviously, every woman has her little insecurities and all her little issues with, you know, trusting a guy. It's just in general, even if that never even happened, any girl's gonna, like, you know, be a little hesitant to trusting her boyfriend. Like me. It happened to me also.

[C]

Wait, wait, wait.

[G]

Stop, stop.

[C]

Your basic premise is that every woman is nervous that her man is gonna cheat on her. So it doesn't.

[F]

It's always in the back of everybody's mind, even with a guy. Like, a girl could be, you know, the dog in the relationship. But with me, it happened when I first met me. My boyfriend. Been together two and a half years now. When we first met, he never told me he had a girlfriend. He was still with her and we were talking for a month and we would be on the phone like all day, all night. So I don't even know when he had time for this girl. And you know, we'd hang up the phone maybe like two, three hours out of the day, and then we'd be on the phone from like 8 o' clock at night till 6 in the morning. I had no clue he had a girlfriend. That the thought never even crossed my mind. And then after a month he told me, well, what would you say if I told you that I had a girlfriend? Are you the type of girl that, you know this and that? And I was like, what the hell, you have a girlfriend? And he was like, kinda. It's been really bad for the last, you know, six months. So I don't really consider her my girlfriend. I was like, well, have you broken up with her yet? And he said no.

[G]

And you stayed with him, what was that? And you stayed with him.

[F]

You know what, that's, that's my biggest regret. Because if I would have known how I was still going to feel till this day, two and a half years later about that situation, I would have never, never, ever, ever put myself through the hell that I've been through the past two and a half years. Because it stays on my mind constantly. I'm always thinking that he's cheating on me. And now my situation is even worse because he has to go out of town and he only comes to see me, you know, every weekend. He has to drive down a three hour drive to come see me every weekend. And I have no trust for him and it's so hard for me. So I advise every girl out there that is in a situation to get out of it as soon as possible because you never get over it and it puts you through hell. Do you see relationships not going to last because you're going to be annoyed and not trusting him the whole time? And it's always going to be in the back of your mind, right?

[G]

Because it goes kind of back what the last caller said about you can't help it. I mean, I agree with Bert. I don't think you can help here. You're attracted to, and those can be extremely powerful feelings, but you have to see through that. I mean, like for her, her regret, like if, if you know someone who's not emotionally attached to somebody, if they said, are you the kind of girl that minds if I'm dating somebody, like all of us in Here, wince like, well, what a jerk. But, I mean, obviously, if you're in love with him, then you're. Oh, well, you know, you wouldn't. You'll do anything to stay with them.

[C]

Sally, if the basis for any healthy relationship, let's assume, is trust, and you don't have it with this guy, then why are you in the relationship for so long?

[F]

You know what? That's what I ask myself every day. And I've been going through so much crap lately, and it's killing me inside. And there's. I don't even know what to do now. You know, it's hell. I mean, we've been going through problems the past couple weeks that he's been absolutely disrespecting me. And it's not only a trust factor now. Now it's disrespect and the trust factor. So I don't even know what to do. I'm extremely confused at this point. And, I mean, I have nowhere to turn because I didn't move to Atlanta that long ago. And I have no friends, nobody to get me away from. From him. And my mind is constantly on him all the time. So I have to find something to do to get my mind off of him, to, you know, just so I can move on, because it just. I know it's not going to work out. The trust issue is too long and.

[E]

Do you have children with this man?

[F]

No. No.

[E]

No children with this man. And you're not engaged to him?

[F]

I'm sorry, what was that?

[E]

Are you engaged to him?

[F]

He wants to come speak with my father. Because where I'm from, it's like a respectful thing to come speak to the dad first and then get his. Get his approval and then give me a ring. Supposedly at the end of this month, he wants to talk to my father.

[E]

But that's where everybody's from, honey. That's a respectful thing for everybody to do. But I think that you need to think about that before he makes that journey to see your father and propose the ring and all that other stuff. You gotta have a lot more respect for yourself than that.

[C]

I mean, you're going into this relationship, you marry this guy, you know it's gonna end up in a divorce, right?

[F]

Yeah. I mean, I feel like such a loser because I don't know what to do and I don't know how to move on and start to get over him.

[G]

It's okay to leave. I mean, the thing is, I think it's so funny how. And. And, you know, I've done The same thing. You are in such turmoil, and you're. You say your life is hell. Well, you know what? If you left, it might get better because obviously where you are is not working.

[F]

I just keep giving myself excuses, like, you know, I can't leave because I'm so lonely.

[G]

Just leave. Just leave. Like, to me, like, you know, instead of over, you know, like, just leave.

[C]

Be lonely for a little while.

[G]

Yeah, I mean, it's okay.

[C]

Is the hell of being alone worse than what you're going through with this guy?

[F]

Probably not. But, you know, it's. My situation, I feel, is a little different because I don't. I work 24 7. I have no friends. I have nothing to do. You know, my parents are, you know, really, really strict. So, I mean, I'm 20 years old, and I can't do anything without, you know.

[E]

Can I tell you.

[G]

Can I tell you why you have no friends is probably. I mean, you don't work 24 hours a day. What you do is you work a lot. In every single moment you spend away from work and sometimes during work is obsessing over this guy and pleasing this guy. If you're single and you have time and you take control of your life, guess what? You get friends, and you get three friends.

[F]

Have not slept in about four days. And the bags under my eyes. I mean, I look sick. Everyone keeps asking me, you know, are you sick? Are you okay?

[G]

Do you realize what you're. Do you hear yourself? I mean, the thing is, you're just. You're Just leave.

[C]

He doesn't have any respect for you because you're not respecting yourself. You're not. You're not taking care of yourself.

[F]

I know that you can do it.

[E]

You can so do it.

[G]

It's okay. I mean, 20 years old, you got.

[E]

Your whole life ahead of you, and somebody's gonna be head over heels in love with you and have absolutely no doubt in their mind they want to be with you.

[G]

Yeah, it's okay. I mean, really, it. Once you leave, it's not. Your life's not gonna fall apart. The problem is your life's falling apart now because you're.

[F]

Yeah.

[C]

So it's so hard to be strong, isn't it?

[F]

Extremely hard.

[C]

I mean, so easy to be.

[F]

At this point, I'm not even sure if it's real love or if I'm just used to him. And I just really. I want to just get over him. I want something to happen. I want to, like, be put in a coma or something just so I can forget this guy ever existed in my life.

[G]

You know what? This is a part of life, you know? And the thing is, like, if you. You have to learn that if you're even questioning whether it's real love, then it's not. You know, like, you really don't love this guy. Yeah. I mean, and it's okay to be single, and it's okay to go make new friends, and it's okay to go hang out with new people. It's okay.

[C]

And, you know, like, everybody's been there. Like, I remember being so insecure. Insecure when I was with women, thinking, well, if I leave her, nobody's gonna dig me as much as she does. There's no way I'm ever gonna find somebody else like that. And I look back at it now, and I kind of laugh at it, because there's. There is. There's a million people out there that are gonna dig you, you know?

[F]

Yeah.

[G]

Yeah. Ladies, don't let the fear of being alone be the reason that you stay in a terrible relationship, because that's not what relationships should be about.

[A]

Yeah.

[C]

Look at Melissa.

[F]

She's been alone for. For almost a year now.

[C]

And have you heard a happier person than Melissa Carter?

[F]

Yeah, she's like.

[C]

She's, like, living in the munchkin Lane, living the dream.

[E]

Hey.

[C]

Hey. Good luck.

[F]

Thanks. Thanks for the advice, guys. I love you guys.

[C]

All right, bye. Bye.

[F]

All right, bye.

[E]

I'm so sad for her.

[C]

It sucks, doesn't it?

[E]

Yeah, that was really, really Sad.

[F]

Remember being 20?

[C]

Oh, that was a stressful time. You're just, like, so learning about yourself, and you're willing to put up with so much crap, you know? But I think you got to go through these. That inevitably gets you to be, like, the strong person, strong man, strong woman that you get to be. But getting through this stuff, it sucks.

[E]

Sucks.

[C]

Bleh. That's my universal this sucks sound. Bleh. Hello, Jackie.

[B]

Hello. How are y'? All?

[F]

He turns it around.

[C]

How are you?

[F]

Good. I love you guys.

[C]

Thank you.

[F]

I've been in this situation, Been in this exact situation, and the situation we're.

[C]

Talking about, getting back to the Desperate Housewives thing, is being the other woman. And then he leaves the one he's currently with. You end up being the woman. Do you ever really have, like, 100% trust in the guy?

[F]

Oh, yeah. Because I was stupid. I mean, I was just absolutely stupid. And then we ended. It was a great relationship. We stayed married eight years, and then at the end of the eight years, we were separated and divorced for 60 days. And on the 62nd day, he remarried the woman that he was with, and he met me.

[C]

Wow. Okay, let me get the scorecard straight here. So he's married. He meets you, falls head over heels for you, drops his wife, ends up with you, married, then divorces you for his first wife.

[F]

Absolutely. But he and his first wife have been separated for two months. When we met, he was living completely apart from her and had already filed for divorce from her. You know, it was over. And then, you know, it was, oh, my God, you know, we're soulmates, you know, and it really felt like that.

[C]

So your angle is, yeah, you trusted him, but you shouldn't have.

[F]

Exactly. Exactly. Because like I said, two days after my divorce was final, he remarried her.

[E]

Can you imagine living in that guy's head where the grass is always greener on the other side? He's like, well, it really sucks now, so I'm going to get out and go over here. Well, this really sucks, too, so I'm going to.

[C]

I mean, I think a lot of people live their life that way, but.

[G]

The difference with him is he's never alone. You know what? He always got what he wanted.

[C]

The Burt Show. The Burt Show.

[F]

Hey, it's Raj and Noah.

[A]

And we're back with a new season of Am I Doing It Wrong? The show that explores the all too human anxieties we have about trying to get our lives right.

[B]

Because we're still doing a lot of stuff wrong.

[A]

But who isn't? That's why each week, we're talking about the topics that we could all use a little helping hit with. Whether it's making new friends as an adult, managing our emotions, or even dreaming.

[B]

We'Ll be talking to experts in their fields who are definitely doing things right. So the rest of us can be a bit wiser and a lot better equipped to handle whatever life throws at us.

[A]

Subscribe now and listen to new episodes of Am I Doing It Wrong? Dropping every Thursday starting January 1st, wherever you get your podcasts.

[B]

And for the first time ever, we're going to have full video episodes on YouTube. Because as long as there are things to get wrong, we're going to be right here to help you do them better.

[C]

Love y'.

[G]

All.

[C]

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