7: Vault: She's never had a long relationship, they want to ask her exe's why.

Summary

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The Bert Show – Episode 7: "Vault: She's Never Had a Long Relationship, They Want to Ask Her Exes Why"

Release Date: May 14, 2026

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Episode Overview

This episode centers around Amanda, a 33-year-old woman struggling to sustain long-term relationships, with none lasting more than a year. The Bert Show team dives into Amanda’s relationship history, exploring her feelings of self-doubt and societal pressure, and collectively brainstorms ways to shed light on why her relationships repeatedly fizzle out. The lively and honest conversation balances humor, empathy, and real talk about modern romance expectations. The show culminates in Amanda bravely agreeing to participate in a “Relationship Report Card,” where ex-boyfriends will give feedback on-air about what went wrong.

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Key Discussion Points & Insights

1. Amanda’s Relationship Patterns

• Amanda has never had a relationship last longer than a year, usually ending after about six months, and is questioning what she’s “doing wrong.”
  • Amanda (01:20): “I’m 33 now, and... usually six months, it starts to go downhill... I want to get married one day. And it’s like, what am I doing wrong?”
• The breakups are usually mutual—not dramatic or contentious.
• Amanda wonders if the issue could be her type, her expectations, or just that she hasn’t met the “right guy.”
• Typically dates men a couple years younger, with jobs and good morals, but admits she isn’t sure what the real issue is.

2. Is There Really a Problem?

• Bert suggests she might not be doing anything wrong and just hasn’t met the right person yet.
  • Bert (01:35): “Is it possible that you’re not doing anything wrong at all, you just haven’t met the right guy yet?”
• Gina admires Amanda’s self-awareness in wanting to break the pattern rather than repeat it without reflection.
• Amanda admits feeling confused but motivated to figure things out now rather than later.

3. Examination of Dating Preferences

• Amanda acknowledges her tendency to date younger men, but finds neither peers nor older men seem to click for her either.
  • Fiona (02:28): “What is your type of guy?”
  • Amanda (02:30): “Usually he’s a couple years younger... I try to find someone that has a job and... good morals. You never know, though.”
• Bert and Fiona joke about Amanda's standards, with playful banter suggesting perhaps she should lower her standards (“get rid of that morals thing or the job”) (02:48–02:55).
• Derek brings up the idea of “dating up” or “dating down,” prompting Amanda to admit her partners may be “a little” below her league, but not in a “crazy” way (04:07–04:24).

4. Societal Pressure & Relationship “Timelines”

• The hosts discuss how women, more than men, often have set life timelines (e.g., married by 28, kids by 30) and feel like failures if they fall behind.
  • Bert (05:09): “My whole flaw in this whole thing is... mostly women... have this life game plan. And when you don’t reach those mental goals... you think you’re doing something wrong when you might not be...”
• Amanda confirms all her friends are married or have kids, amplifying the pressure she feels (05:52).
• Fiona and Gina note the generational shift: women are now more career-focused, in contrast to their mothers’ and grandmothers’ generations (05:55–06:31).
• Wendy (age 24) shares her own insecurities about not being in a long-term relationship, feeling “insignificant” compared to friends who are (07:04–07:35).

5. Gender Differences and Self-Worth

• The cast explores how women may define themselves by their relationships more than men do, despite changing career roles.
  • Gina (07:47): “I think women define themselves by their relationships more so than... guys do.”

6. The “Relationship Report Card” Proposal

• The hosts propose reaching out to Amanda’s exes to get candid feedback on why her relationships ended—a recurring bit called “Relationship Report Card.”
  • Bert (08:03): “...you would give producer Tracy, like five or six or seven phone numbers of ex-boyfriends... he gives us a snapshot of why it didn’t work out and what your responsibility in that was.”
• Amanda bravely agrees, saying she has nothing to lose (08:47).
• The group recalls a memorable time when a previous participant learned from her exes that she drank too much—information she initially resisted but proved revealing (08:54–09:06).
• This time, the show plans to only have Amanda check back in on Friday for all the exes’ input, giving her time to reflect before responding (09:09).

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Most Memorable Quotes & Moments

• Amanda’s anxiety and vulnerability:
  • “I just want to stop and figure out what the problem is now.” (04:51)
• Bert’s broader perspective:
  • “Wouldn’t you rather be 35 years old, though, and end up with a guy that’s right for you for the rest of your life than 28 years old and have a divorce behind you and still searching for that guy?” (06:18)
• Wendy’s open confession:
  • “You always feel like a failure when you’re not in a relationship...” (07:17)
• Bert’s humorous jab at gender standards:
  • “Women are so picky now, man. It was so much easier when I was dating. There were no morals at all!” (03:01)
• Amanda’s courage:
  • “I have nothing to lose.” (08:47)
• Show’s supportive but teasing tone:
  • Bert (09:51): “You are brave.”
  • Derek (10:18): “It’s like thanking the cop who gave you a ticket.”
  • Bert (10:20): “She may not be thanking us at the end of the week.”

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Key Timestamps

• 01:20: Amanda explains her relationship history and why she’s seeking advice.
• 02:28–02:51: Amanda discusses her dating preferences.
• 03:01: Jokes about women’s high dating standards.
• 05:09: Bert unpacks the pressure of life timelines for women.
• 05:52: Amanda confirms all her friends are married/pregnant, highlighting her sense of isolation.
• 07:04–07:35: Wendy’s candid perspective on relationship-related self-worth.
• 08:03: The introduction to the “Relationship Report Card” segment.
• 08:54–09:06: Anecdote about a previous guest learning they drank too much from ex feedback.
• 09:09: Plan for Amanda to hear from exes separately, then return Friday for her response.
• 10:15: Amanda thanks the hosts for the opportunity and agrees to participate.

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Tone & Takeaways

The conversation is authentic, caring, and honest—with a signature layer of The Bert Show’s humor and willingness to address awkward truths. The cast validates Amanda’s insecurities while challenging her to open up to uncomfortable feedback. The impending “Relationship Report Card” segment promises both drama and insight, offering Amanda and listeners the chance to strip away self-doubt and discover what might really be going on beneath the surface of short-lived romances.

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For listeners who missed it:
This episode is a compelling snapshot of modern dating anxieties and self-exploration—with the Bert Show’s warmth and wit turning one woman’s romantic confusion into a vulnerable, relatable conversation that could lead to true self-discovery.

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Transcript

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[Bert]

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[Bert]

Did you guys catch what? Our caller's name is Amanda. Amanda. Hey, Amanda.

[Derek]

I heard you're on the air.

[Bert]

Hi, how are you?

[Amanda]

I'm doing good. How are you guys doing?

[Bert]

Okay. You know, from time to time over the last eight years, we will get an email just like yours that is just. You're just confused by guys, you know, I think there's always a bubbling confusion about the opposite sex, but at some point you're just like, why isn't this working for me? And I think you're probably there right now.

[Amanda]

I am, yeah.

[Bert]

Is this a recent breakup we're talking about that brought all this sort of introspection on?

[Amanda]

Well, I'm 33 now, and it's like I've never had a relationship last more than a year, you know, usually six months. It's 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?

[Bert]

Is it, you know, I think I say this every time we do this. Like, is it possible that you're not doing anything wrong at all, you just haven't met the right guy yet?

[Amanda]

I don't know. I mean, it seems like, you know, I've dated quite a few guys and it's like it just never, for whatever reason, you know, after the six month period, it just starts to go downhill.

[Fiona]

And is it usually your choice to get out of the relationship or their choice?

[Amanda]

It's usually mutual. I mean, you know, once or twice I dump someone or they dumped me. You know what I mean? It was never like a crazy breakup, really. It was like more of a mutual thing.

[Gina]

But I admire the fact that you want to just stop the process right now. Not, not to repeat the pattern. If there is A pattern and try to do something different, you know, but it could be a case where, like Bert said, it just hasn't worked, know.

[Amanda]

Right. And I mean, I don't know if it's, you know, the type of guy they date. I don't know, it's very weird.

[Fiona]

What is your type of guy?

[Amanda]

You know, usually. Usually he's a couple years younger. Not very, like, not significantly younger, but a couple years younger. And, 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?

[Bert]

Maybe you're setting the bar too high. Maybe you got to get rid of that morals thing.

[Fiona]

Or the job.

[Bert]

Or the job. Yeah. One of the others gotta go casting with a wide net.

[Derek]

They just have to. They don't. They have to know killing is bad and they have to get a paycheck.

[Bert]

Women are so picky now, man. It was so much easier when I was dating. There were no morals at all. So much easier. What happened with the last guy that you were dating? Why did you break up?

[Amanda]

I don't know. I mean, it was going great. And then again, like at like seven months, I mean, we just. I don't know, he started to get aggravated with me and I started to get aggravated with him. I don't know if it's like, like I'm very, you know, I'm very into work and, you know, I consider myself well read and I think. I don't know if that's intimidating to him. I mean, he was super, you know, super sweet. Everything was going great at first, and then, I don't know, I got busy with work, he got busy with work, and it was like, just kind of fizzled out.

[Bert]

Who did the breaking up?

[Amanda]

It was totally mutual last time.

[Gina]

Who started the conversation?

[Amanda]

I did.

[Bert]

Okay, so you broke up with him then.

[Derek]

It was mutual.

[Bert]

Never.

[Amanda]

It was mutual. I mean, like, it really was mutual, though.

[Derek]

Do you date people who are better or worse looking than, you

[Amanda]

know? I don't know. I mean, worse.

[Bert]

She doesn't want to say that.

[Gina]

Not to be your interpreter.

[Derek]

I'm sorry, dude. I mean, do you find yourself. Do you think. Do you think that you date down?

[Amanda]

No, I don't think I date down. I don't. I mean, maybe a little, but nothing

[Derek]

crazy, but I know if we were all hanging out and we looked at you and the guy that you're dating, you know, average guy that you're dating in a restaurant, would it be. Who would be the Lucky one in the relationship. Him or you?

[Amanda]

Him. Okay.

[Wendy]

Have you tried dating guys your age?

[Amanda]

Yeah, I have. They don't work either. Really?

[Fiona]

What about older guys?

[Amanda]

I haven't really dated older guys.

[Fiona]

Okay.

[Amanda]

You know, so maybe, I don't know. I mean, I just want to stop and figure out what the problem is now.

[Bert]

Did you have a game plan, like a marriage game plan, like you were going to be married by 28 years old?

[Amanda]

Yeah, I did. I mean, I thought so, you know, at a younger age. And then you hit 29 and you're like, okay, maybe I need to get rid of that plan.

[Bert]

Here's my whole flaw in this whole thing is like. And I think this is mostly women that have this Life game plan. 28 years old, I'm gonna be married. 30 years old, I'm gonna have my first kid. 32, second kid. And when you don't reach those mental goals of yours, then all of a sudden you're doing something wrong when you might not be doing anything wrong at all. You just haven't found the right guy. You haven't rushed into a relationship that you don't belong in that ended up in a divorce anyway. Maybe you've just. Wait, he just hasn't come along yet. Why do women panic like that?

[Gina]

Well, because we're in a pack and we seem, I think, I think we feel behind. Because the people we're around a lot of the times and feel the pressure. Because if she's 33 and are all your friends married?

[Amanda]

All of them. All of them are pregnant or have babies. Right.

[Fiona]

I think that's it. I mean, I think it's the ovary time clock more than anything that puts the pressure on it. Yeah, well, and a lot of times you want to follow in the footsteps of your mom or what your family did. And most of our moms didn't. Didn't pursue careers like we all do. I mean, she said that, you know, the last relationship fizzled because she was really focused on work. Well, how focused was our mother's generation or our grandmother's generation? Focused on their careers like nil in comparison to what we are.

[Bert]

Wouldn't you rather be 35 years old, though, and end up with a guy that's right for you for the rest of your life than 28 years old and have a divorce behind you already and still searching for that guy?

[Gina]

I think so. But I think what is saying is correct, that this generation has to do it ourselves. Like the expectation is kind of old fashioned on what you know, because our mothers and grandmothers were married young and had children young. And like she said, with the career thing. So I think we have to define it in our own head what our life is going to be like. And then, I mean, I never had a mother that was in my ear about what I needed to be doing. But a lot of women have their mothers telling them, hey, you know, it's clock's ticking yet, you know, I mean, it's just all this feedback you get from everybody, wanting to please everybody.

[Bert]

Wendy, you're how old now?

[Wendy]

24.

[Bert]

24 years old. Do you feel like because you're not in a steady relationship right now that you've done something wrong?

[Wendy]

Absolutely.

[Amanda]

Really?

[Wendy]

I mean, it's. Yeah, almost a year since I've been in like a year and a half longer since I've been in a relationship.

[Fiona]

Yeah.

[Wendy]

You always feel like a failure when you're not in a relationship. Really? For that long. Yeah, because I want to get married eventually, but everybody else has relationships. Like producer Joanna. She's been in her relationship for a year and a half and she's 25. Have you feel like insignificant to your friends and people who are in long term relationships?

[Derek]

Have you considered working out and doing something different with your hair?

[Wendy]

I tried that. Doesn't work.

[Bert]

Maybe you're just not doing anything wrong at all. Maybe you're.

[Wendy]

Maybe. But you always feel like you are.

[Bert]

Really?

[Gina]

I think. Well, I think. And women, I think, define themselves by their relationships more so than. And hopefully their careers too now. But I think women define themselves as more important in a relationship than out of one. More so than guys do.

[Bert]

Well, here's what we can do for you. And we've done this from time to time. See if you're hip to this. We do this segment called Relationship Report Card where what you would have to do is you would have to give producer Tracy, like five or six or seven phone numbers of ex boyfriends. And then what we do every morning is we get another ex on and he comes completely clean on what happened in the relationship and his attitude, your attitude towards the relationship. And he just gives us a snapshot of why it didn't work out and what your responsibility in that was. And then at the end of the week, at least in the past when we've done this, we've had some. I mean, it's been pretty conclusive on exactly why these guys have been turned off. If you want to try that, it's a gutsy move because listening to all those guys has got to be tough.

[Amanda]

Yeah. No, but I would. I mean, what do I have to lose? I have nothing to lose.

[Gina]

And it can be valuable information. I mean, in the past, when we've done it, it's valuable information.

[Fiona]

One girl, didn't she kind of find out that she drank too much? Yeah, yeah, Remember that one?

[Bert]

That's right.

[Derek]

She never admitted it.

[Fiona]

She didn't really admit it, but it was, like, consistent. Every single guy was like, well, she's fine until she gets wasted.

[Bert]

And then she fought it and fought it and fought it.

[Fiona]

Yeah, yeah.

[Bert]

No, and. And in thinking about this yesterday, Jeff and I were talking about this. I think the way we'll do this that's a little bit different is in the past, every time we've had an Exxon had the Burt show listener on who has argued and argued and argued and wouldn't listen after a while because they just don't want to hear what's coming out of the ex's mouth. So I think what we're gonna do is we'll have the ex on every day, and then we'll only check back with you on Friday. So if you want to go ahead and you want to rebut, Friday is the day, but you'll have all week long to chew on everything that they said to you.

[Gina]

That's a good idea.

[Amanda]

Okay. Okay, now totally. I'll give Tracy all my. The information. Okay.

[Bert]

So if it works out right, then on Monday morning, we'll have the first ex on.

[Fiona]

You're a brave girl.

[Bert]

You are brave.

[Fiona]

That could be pretty brutal.

[Wendy]

Honesty.

[Bert]

It's really brutal.

[Gina]

I love that.

[Bert]

All right, let me put you on hold, and we'll get some info from you, and we'll see if we can get one of your exes to come on with us. They're not real eager to do this either. It takes a lot of arm, you know, twisting, because they're like, man, it's over. It's behind her. Does she really want to know this? And the truth is, yes. And we have a tough time convincing them that you really want to hear this. So let's see if we can get one on on Monday morning.

[Amanda]

Okay, awesome. Thanks, guys, so much.

[Bert]

You're welcome.

[Derek]

It's like thanking the cop who gave you a ticket.

[Bert]

She may not be thanking us at the end of the week. Hey, the bird show.