Vault: She Gives Up on Figuring Out Her Breakups

Summary

The Bert Show – "Vault: She Gives Up on Figuring Out Her Breakups" (May 19, 2026)

Episode Overview

This episode of The Bert Show dives into a vulnerable listener segment featuring Amanda, a 33-year-old woman reflecting on her persistent challenges in relationships. Over several days, the show has been contacting Amanda’s ex-boyfriends to candidly share why their relationships ended, aiming to identify patterns and provide Amanda with honest feedback for future growth. The episode captures Amanda’s emotions as she listens to unfiltered commentary from her exes and discusses with the hosts and callers what these insights reveal about relationships, compatibility, and self-perception.

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Key Discussion Points & Insights

Amanda’s Relationship History and Motivation

• Amanda opens up about her dating history and growing concerns:
  • "I'm 33 now, and I've never had a relationship last more than a year. You know, usually six months. It starts to go downhill and it's just like you start thinking at a certain age, I want to get married one day. And it's like, what am I doing wrong?" (Amanda, 01:35)
• She typically dates men slightly younger than herself, seeking those with jobs and good morals, though she admits, "You never know, though. You know what I mean?" (Amanda, 01:57)

The Show’s Approach to Finding Patterns

• The hosts have reached out to four of Amanda’s exes, collecting feedback on why things didn’t work and saving Amanda’s response until later to ensure she digests the information:
  • "We were trying to just pick up a pattern. And so all we needed was the perspective of the ex boyfriends, their perspective." (Tobias, 02:54)
  • "If you're on every day defensive, it's not doing you any good, right?" (Host, 03:25)

Amanda’s Reaction to Feedback

• Amanda struggles with hearing herself described as "boring" by her exes:
  • "But like they're calling me boring... It just makes me angry." (Amanda, 03:52)
  • She emphasizes her busy lifestyle: "I'm just super. I'm a super busy girl." (Amanda, 04:20)
• The hosts encourage Amanda to focus on the constructive side:
  • "You're hearing that much more loud and clearly than what compliments they're giving you, too... just that your lifestyle choices at the time that you dated didn't line up." (Melissa, 04:28)
  • "You're letting your ego get in the way of, like, getting some really good input here." (Host, 04:48)

Listener Call-Ins and Community Feedback

• TC, a caller, offers tough love:
  • "If your boyfriend say you're boring, that means you're boring." (TC, 06:46)
  • Melissa counters: "Don't you think that that means she's picking guys that aren't the right match for her?" (Melissa, 07:08)
  • The group discusses how "boring" is subjective, often depending on lifestyle compatibility.

Self-Sabotage and Rushing Relationships

• TC offers another perspective, observing that Amanda might check out of relationships prematurely:
  • "She would get into a relationship, and before the relationship progressed, she changed up and then broke the commitment... the same thing she's doing right now." (TC, 08:34)
• Amanda acknowledges she potentially doesn’t give things enough time:
  • "I don't think I give it enough time to get established before I really, like. You know, I don't give it enough time, I think is a problem, and I'm very rushed." (Amanda, 09:21)

Emotional Defensiveness and Self-Image

• The hosts and callers note people often miss positive feedback when emotionally invested:
  • "You're so focused that you're not listening to what anybody's saying." (Host, 11:19)
  • Jackie makes a relatable analogy: "Just like when you look at a picture that has 200 people in it... What's the first thing you scan for? Yourself. And you are hypercritical." (Jackie, 11:43)

Commitment to the Process

• Despite discomfort, Amanda agrees to continue for another day to gain further insights:
  • "All right. Well, I mean, you know, what's another one?" (Amanda, 10:04)

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Notable Quotes & Memorable Moments

• “I want to get married one day. And it's like, what am I doing wrong?”
  — Amanda (01:35)

• “We were trying to just pick up a pattern... all we needed was the ex boyfriends' perspective.”
  — Tobias (02:54)

• “You're letting your ego get in the way of, like, getting some really good input here.”
  — Host (04:48)

• “If your boyfriend say you're boring, that means you're boring.”
  — TC (06:46)

• “You're attracted to guys that are opposite from you… once you're in it, you're really not a big fan of it, right?”
  — Host (07:25)

• “I don't think I give it enough time to get established... and I'm very rushed.”
  — Amanda (09:21)

• “Just like when you look at a picture that has 200 people in it... What's the first thing you scan for? Yourself. And you are hypercritical.”
  — Jackie (11:43)

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Important Segment Timestamps

• 01:31 — Amanda describes her dating struggles and short relationships
• 02:54 — Hosts explain the experiment’s purpose and process
• 03:52 — Amanda reacts to being described as "boring"
• 06:46 — TC calls in, bluntly commenting on Amanda being "boring"
• 08:34 — TC suggests Amanda changes or ends commitments early
• 09:21 — Amanda explores whether she rushes or self-sabotages
• 10:04 — Amanda agrees to continue the experiment
• 11:43 — Jackie’s analogy on self-criticism and missing the positives

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Summary & Tone

The episode maintains a candid, supportive, and occasionally tough-love tone typical of The Bert Show. The hosts and callers push Amanda to reflect honestly on her choices while also unpacking broader issues of compatibility, perception, and emotional response in relationships. While Amanda is initially defensive, the segment closes with her willingness to keep seeking feedback—with an undercurrent of empathy from both hosts and listeners.

Listeners unfamiliar with previous episodes will find this one deeply engaging for its raw, relatable exploration of dating patterns, self-reflection, and the challenges of truly hearing constructive criticism from those closest—and sometimes from ourselves.

Transcript

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[Host]

It's the virt show. All right, so this was Amanda a couple of days ago. She was into it.

[Amanda]

Well, I'm 33 now, and I've never had a relationship last more than a year. You know, usually six months. It starts to go downhill and it's just like you start thinking at a certain age, I want to get married one day. And it's like, what am I doing wrong? You know, once or twice I dumped someone or they dumped me. You know what I mean? It was never like, crazy breakup. Really.

[Melissa]

What is your type of guy?

[Amanda]

Usually he's a couple years younger. You know, I mean, I try, you know, to find someone, you know, that has a job and, you know, I think has good morals. You never know, though. You know what I mean?

[Host]

So she agreed every day we're supposed to have another ex boyfriend on that was gonna detail why the relationship didn't work out. We're three days into it, this would have been the fourth, and I think it's been pretty successful so far.

[Melissa]

Well, we definitely found a pattern between number one and number two. And the number three was totally different, but still gave a very clear explanation on why the relationship didn't work.

[Host]

It has been pretty interesting to read the emails though, because I got a whole bunch yesterday that were sort of playing psychologist with her. That said one of two things that I'll tell you about after we talk to Amanda here. Hey, Amanda.

[Amanda]

Hi guys.

[Host]

You're not feeling so good about this.

[Amanda]

No, come on. I just like it's such a one sided thing because I should be on the phone asking some of the questions.

[Tobias]

Well, no, no, because the, the issue was Amanda, that you wanted to see, you know, what you could do to improve the future. And we were trying to just pick up a pattern. And so all we needed was the perspective of the ex boyfriends, their perspective. And so the reason that we didn't want to have you on until Friday was because we knew, I mean, with any of us, if our exes are on saying something about us we don't agree with, we'd be ready to go right at it. But that's not gonna help what we're trying to accomplish here, which is to see a pattern form on why the relationships aren't working from their perspective.

[Host]

And we've done this before and we knew what your knee jerk reaction would be. So the intention this time was to let you chew on it for a couple of days and then you come on on Friday or you come on on Monday and you go, okay, you remember when Nathan said this? Well, this is why I don't agree with that. You remember when John said this? This is why I don't agree with that. Or you take a couple of days to chew on it and you go, okay, you know what? I, maybe these dudes are right, but if you're on every day defensive, it's not doing you any good, right?

[Amanda]

100%. But like they're calling me boring. Like there's, you know, explanations for why. I mean, it just makes me angry. Like they're calling me boring and they're saying things and it's like I can't rebut because, you know, I mean, what about what they did and what about. I don't know.

[Tobias]

But that's not what this is about. And every single one of them complimented and said, you're a great girl.

[Host]

And this is about their perception. This isn't about their side of the whole thing. This is what they consider the end of the relationship.

[Amanda]

Right. I mean, it just aggravates me that they're calling me boring when I'm not boring. I'm just super. I'm a super busy girl.

[Melissa]

Well, and I think that. I think Melissa's right. I think that it's easier for you to hear the criticisms and the critiques, which is kind of the point of this. But you're. You're hearing that much more loud and clearly than what compliments they're giving you, too. I mean, they're talking about what an awesome girl you are and all these things, but just that your lifestyle choices at the time that you dated didn't line up.

[Host]

You're letting your ego get in the way of, like, getting some really good input here.

[Tobias]

And that's what you came to us for.

[Amanda]

Right.

[Tobias]

And it's hard to hear. I mean, we. We've said that from the beginning. It's hard to hear.

[Amanda]

Yeah, I don't think it'd be. I didn't think it'd be this hard.

[Tobias]

Yeah. My ex girlfriends wouldn't say anything nice about me. I mean, I don't think some. I think some of them. Yeah. Would. Because there's a reason you broke up. And what they're going to remember is the end of the relationship, not the begin. So whatever we disagreed on at the time of the breakup is what they're gonna say.

[Host]

See, I want to attack that from a totally different angle. Like, you don't think that when you look back at your past relationships, you look at them fondly. Like, I don't remember most of my breakups because they weren't that bad.

[Tobias]

No, I do. I mean, I do. I'm proud of. Except for maybe one. But I'm proud of most of. I'm proud of all but one of the women I dated, and I'm not. And it's not that there's not a good rapport between me and my ex girlfriends, but if we came on and said Melissa needs advice on what she needs to seek in a partner for relationships, then what you're doing is you're telling the person what was wrong, why it didn't work, and that's all they're focusing on, you know, and they're focusing on the fact that their lifestyle did not match yours, and that's it. And the reasons why so that you know what to seek out in the future that will be compatible with you.

[Host]

I think most people in their heart of hearts would want to know what happened in the relationship, but it just isn't acceptable for you to call up and go, okay, give me 100% truth. Because you don't have to think that the guy is going to or the woman is going to here. You're getting that opportunity. They have nothing to lose right now.

[Amanda]

And I agree. I mean, it's just. It's really, you know, because I don't look at myself as boring. I don't like to go out, I don't like to party, but I don't look at myself as boring. And it. With the born again virgin thing, I mean, that was something totally, you know, like we. I thought we were going to get married, and I really wanted it to be special when we did get married.

[Host]

Now, hold on one sec, because you're doing exactly what we didn't want you to do. Good morning. Is it Tobias?

[TC]

Yes.

[Host]

Hey, how are you this morning?

[TC]

I'm doing good. I want to tell the caller that if your boyfriend say you're boring, that means you're boring.

[Melissa]

No, from this point of view, because everyone.

[TC]

If everyone says you're boring, you got three or four boyfriends. Now, you might disagree with them. Okay, you can disagree. They all think you're boring. That means you're boring.

[Melissa]

Don't you think that that means she's picking guys that aren't the right match for her?

[Tobias]

Yes.

[TC]

No, it means she's boring to them. That's their perspective.

[Melissa]

Right, right. Which makes the wrong guy so boring.

[Tobias]

No, to those particular men. Because people I find boring are not going to be the same people that. Like Jen or Wendy. Fun, boring, you know, I mean, what

[Host]

it says is that you're attracted to guys that are opposite from you. You are attracted to guys that are exciting, that like to go out. You like that lifestyle from the outside looking in, but once you're in it, you're really not a big fan of it, right?

[Amanda]

Yeah, no, I don't like it. I mean, I don't like to go out. I really don't drink. You know, and there's gonna be. And I have friends, but because I don't drink, I don't think that makes me boring. And I think that's. The guys that I dated really thought that.

[Melissa]

That's what we're trying to figure out here. That's what we said at the beginning of this whole thing, is we said we're Gonna either recognize patterns in your behavior or patterns in the type of guys you pick. And I think we're learning both.

[Host]

And you got to remember the guys that have said that you were boring, equated boring to not drinking. They were 21 years old, so. To a.

[Amanda]

Well, that was a. Yeah, that was a. That's not a normal occurrence that he's that young. It's really. I know. That was like. I mean, I usually only date a few years younger.

[Tobias]

Amanda, you're just being defensive.

[Host]

This is exactly what we didn't want

[Tobias]

to happen, and that's why we didn't have you on with each one. Because instead of getting practical information and a solution for you, it would end up being.

[Host]

Here's TC Hey, TC Hey.

[TC]

How's it going?

[Host]

Good.

[TC]

Yeah. I just wanted to say to Amanda that I didn't get the oppression from the exes that she was boring. The impression that I got was that she would get into a relationship, and before the relationship progressed, she changed up and then broke the commitment. You know, something changed up within her. You know, the same thing she's doing right now. All right. She's had a couple of days with it. Okay. I don't like it. Let me just get out of it.

[Host]

Yeah, you committed to us, and now

[Jackie]

you're breaking up, and you gave everybody else six months. You're not even. You haven't even given us one week.

[Tobias]

But TC Made a good point. Now, that. Do you. In a relationship, is there a possibility that when you get in there and you don't like it, that you kind of sabotage it?

[Amanda]

I don't think I sabotage it. I think that, like, I think that I want to put a relationship in front of work, and then I get busy, and I just kind of, you know, I don't think I give it enough time to get established before I really, like. You know, I don't give it enough time, I think is a problem, and I'm very rushed.

[Host]

I still don't think our test group is large enough yet. Like Tracy said, can we do this one more day? Cuz, like, your latest. Your latest ex wants to come on, and he's really eager, like, he knows exactly what this is all about. He doesn't want to come on here and rip on you. He just thinks that he's got some things to say that would really help you open up this whole thing.

[Jackie]

We're trying to help.

[Host]

Yeah, one more day, please.

[Tobias]

This is not bashing Amanda. This is helping Amanda.

[Host]

Give us one more day, please.

[Melissa]

Pretty please.

[Amanda]

All right. Well, I mean, you know, what's another one?

[Jackie]

So what. How about.

[TC]

Okay.

[Melissa]

Oh, Amanda, don't sell past the. Yes.

[Jackie]

That's why I stopped.

[Host]

The hard sell is over. We'll talk to you later.

[Melissa]

Okay, bye.

[Amanda]

Oh, well, all right.

[Host]

We're gonna have your latest.

[Jackie]

Seriously. Goodbye.

[TC]

Bye.

[Commercial Narrator]

Bye.

[Amanda]

Okay. Talk to you guys later.

[Melissa]

Okay.

[Tobias]

But that's. I mean, yeah, that's.

[Host]

We're recording today. Right. That is a archive.

[Jackie]

That's a binding contract.

[Tobias]

But that's natural to feel that way. But it's just. Yeah. It's hard to detach those emotions and get defensive.

[Host]

Here's Jackie. Good morning, Jackie. You're on the Burt Show.

[Jackie]

Hi.

[Amanda]

Hey.

[Host]

Hi.

[Amanda]

I just wanted to tell her I know she's gone, but Chip weren't really calling her specifically boring. They were just saying that at the end of their relationship, the relationship had kind of gotten stale or boring. They weren't. All of them complimented her in every way. Smart, she's pretty, she's fun, blah, blah, blah. And then at the end, they were like, yeah, well, she wanted to study and be exciting in her career, not exciting at the bar.

[Host]

Right.

[Jackie]

Yeah.

[Amanda]

I think she just was misreading what was what they were saying. They weren't being personal about it. They were just saying that the relationship had gotten.

[Host]

Well, we have said this before also, that when you're really passionate about something, you're close to others opinions. Like, there are some times where you just don't hear the debate because you're so passionate about it. And you're never gonna be more passionate about anything than you are about yourself. And so here they are. They're trying to give her help, but she's so focused that she's not listening to what anybody's saying.

[Tobias]

She's hearing the negative things.

[Jackie]

Just like when you look at a picture, you could look at a picture that has 200 people in it. What's the first thing you scan for yourself? And you are hypercritical. You know, oh, that shirt doesn't look good on me. One eyes closed. You know, whatever. Hair's crappy, all this. Blah, blah, blah. Even though you're fine, you know, everybody else looks at the pictures. Oh, what a great picture of all y'. All.

[Host]

It's a tough thing.

[Jackie]

It's the same thing she's doing.

[Host]

That is not easy. All right, so we'll get the latest ex boyfriend on, and he says he's got some info that can open up this whole thing here.

[Commercial Narrator]

Birch.

[Host]

Yeah.

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[Commercial Narrator]

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