33: Vault: Her Ex Breaks Down What Went Wrong

Summary

The Bert Show – Episode 33 Vault: "Her Ex Breaks Down What Went Wrong"

Release Date: May 18, 2026
Main Theme:
In this episode, the Bert Show reconnects with Amanda's ex-boyfriend, John, to understand why Amanda's romantic relationships never last more than a year. The show aims to explore her patterns through the lens of her previous partners, with the hope that honest feedback will give Amanda—and listeners—insight into why her relationships falter.

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Episode Overview

• The team revisits a previous caller, Amanda, who struggles to maintain long-term relationships and suspects she might be the problem.
• Amanda’s pattern: Brief relationships (less than a year), usually with younger men, and a desire for more lasting, serious connections as she’s now looking to settle down.
• Amanda agreed to let the show contact her ex-boyfriends for candid feedback, but the hosts tweak the format to avoid live confrontation and defensiveness.

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Key Discussion Points & Insights

Setting the Stage: Amanda’s Relationship Troubles

[01:59-02:28]

• Host 1: Amanda wonders, “I must be doing something wrong," after a string of short relationships.
• Host 2: Emphasizes Amanda’s readiness for something serious and the wish to understand her failed relationships.
• The show’s approach: Speak to Amanda’s exes individually and have Amanda listen later, to encourage open feedback and prevent defensiveness during the conversation.

Interview with John (Amanda's Ex from College)

[03:33-10:43]

• Background: John dated Amanda 13 years ago in college. He participates with a disguised voice to avoid personal conflict, as he’s now married.
• Early Relationship:
  • Relationship began with lots of excitement—going out, parties, movies, time with friends.
  • “We hit it off…we had a lot of fun.” (John, [04:31])
• Transition Point:
  • After about six months, Amanda shifted from being outgoing to becoming more of a homebody.
  • John notes: “She just got really kind of, I guess to me as a 21-year-old, kind of like homebody-ish. It felt like we were in our 30s all of a sudden.” (John, [05:36])
  • Amanda became very focused on academics—studying, avoiding social outings, prioritizing grades.
• Growing Apart:
  • John felt forced to stay in if he wanted to spend time with Amanda, leading to boredom.
  • “It was kind of like if I wanted to hang out with her...then I had to stay home.” (John, [07:27])
• Host Reflection:
  • Hosts suggest Amanda might have been “selling in the beginning,” putting her best, most fun self forward for the honeymoon period before reverting to her focused and reserved personality once comfortable.
  • “You put the face on initially...then inevitably you end up being who you are.” (Host 1, [08:46])
• John’s Perspective on Amanda:
  • John believes her more serious, studious side was her genuine self.
  • “[She’s] very ambitious and focused...which, you know, I’m not going to fault anybody for…” (John, [08:04])
  • He reflects that their goals and energies didn’t match at the time.
• Breakup Details:
  • Nothing dramatic; both seemed to naturally drift apart as interests and lifestyles diverged.
  • “It didn’t even...end that badly. It was just kind of an understanding.” (John, [09:45])
• No Lingering Feelings:
  • John laughs off any idea of missing Amanda or thinking of her often.
  • “Oh no, no, not. I mean, you know, no.” (John, [10:09])
  • He notes sometimes seeing her in old pictures but feels nothing significant.

Notable Host Reactions & Commentary

[06:59-11:03]

• Hosts summarize: Amanda craved fun and excitement at first, then shifted gears into seriousness and homebody habits—potentially a sign of authentic personality emerging after the dating “honeymoon phase.”
• Host 1: “She put on one face to begin with, and then she became focused again, and you lost interest easy.” ([09:36])
• Host 2: “Not too crazy, got more homebody-ish.” ([11:00])
• Commentator: “Just wanted to settle down faster, maybe, but nothing wild and crazy.” ([11:03])

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Notable Quotes & Memorable Moments

• "She just got really kind of, I guess to me as a 21-year-old, kind of like homebody-ish. It felt like we were in our 30s all of a sudden."
  — John, [05:36]

• “It was kind of like if I wanted to hang out with her, which I did, then I had to stay home.”
  — John, [07:27]

• “You put the face on initially...then inevitably you end up being who you are.”
  — Host 1, [08:46]

• "It didn’t even...end that badly. It was just kind of an understanding."
  — John, [09:45]

• "Do you miss her?" "Oh no, no, not. I mean, you know, no."
  — Host 3 and John, [10:07-10:09]

• (Joking exchange about whether he ever thinks of Amanda during intimate moments with his wife. The group laughs and shifts away quickly.)
  — Host banter, [10:19-10:27]

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Timestamps of Important Segments

• [01:59] – Hosts introduce the segment and Amanda’s situation
• [03:33] – John joins; relationship background begins
• [04:31-05:36] – John describes the change in Amanda’s behavior
• [07:27] – John explains the homebody dynamic
• [08:04] – John theorizes on Amanda’s true personality
• [09:45] – John reflects on how things ended
• [10:07-10:09] – Direct question about missing Amanda
• [10:46] – Hosts wrap up with summary and foreshadow next steps

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Final Thoughts

This episode provides a candid look into relationship dynamics through the lens of hindsight and honest reflection. John’s story suggests that Amanda’s pattern may stem from an initial push to impress, followed by a retreat to her true, more studious and settled self, causing disconnects with more free-spirited partners. The hosts keep the tone light yet insightful, mixing empathy with humor, and tease further feedback from other exes in upcoming episodes—giving listeners both answers and anticipation for more real-world relationship lessons.

Transcript

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[John (Amanda's Ex-Boyfriend)]

n the first show.

[Host 1]

All right, let's get John on the phone here. It was Amanda that called us on Friday and she's just looking back at her relationships and she's like, I'm doing something wrong. I must be doing something wrong.

[Host 2]

Yeah, she just wants to figure out why she doesn't have a relationship that lasts longer than about a year. She's at that stage where she's ready to sort of start a family and have something more serious, and all of her relationships just don't seem to work out. So the only thing she really told us on Friday was that she often dates younger guys, but that was about it. And so we're gonna talk to all of her old boyfriends and figure out what's going on.

[Host 1]

Now, the way we're doing it, this. That we've done it differently, that we're doing it differently is that normally we would have the initial caller on, but they got so defensive that the whole thing sort of went to crap by the third day.

[Host 3]

We can play the role of the other of. Of the original Amanda. Yeah, we could play the role of Amanda afterwards just by going, that's so not true. That's not. That never happened that way. That's what he was like, whatever.

[Host 1]

So what we're hoping is Amanda is listening right now, and she'll listen to what John has to say here, and then she'll chew on it for a couple of days so she doesn't have this initial defensive attitude. Then we'll get her on either on Friday or Monday, and we'll talk about all the exes that we had on. But this would be difficult to listen to for any of us.

[Host 3]

If we were a decent radio show, we'd have Carrie Pusheen doing this.

[Commentator]

They're leaking tapes. They're not really talking tapes. Yeah, but you're always kind of in denial of anything you're doing wrong, and you don't want to believe that you're doing anything wrong. A relationship, and you want to think everything's cool with you, but when somebody tells you it's not. Yeah. You're gonna deny it.

[Host 1]

Well, anytime anybody gets critical about you, you're defensive. Right. But she said, go for it. So here is John, and this is one of her boyfriends from college. So we're going back 13 years here, and he wants to be on the voice disguiser because he's married now, and I don't think his wife knows he's doing this. Hey, John.

[John (Amanda's Ex-Boyfriend)]

Hey. Good morning.

[Host 1]

Good morning. You're on the voice disguiser.

[John (Amanda's Ex-Boyfriend)]

Oh, good. Yeah, I don't know if it'd be a problem, but I just, you know, I'm trying to avoid any conflict, possibility, a problem, you know?

[Host 1]

Yeah, I'm sure it wouldn't be. I mean, it was 13 years ago. When is the last time you even Talked to her.

[John (Amanda's Ex-Boyfriend)]

It was probably about 12 and a half years ago and we dated. Yeah, it was 13 years ago. Now.

[Host 1]

People change a lot over the years, but this may give us like an initial snapshot of what Amanda's like in relationships. So why don't you just sort of tell us what your time was like with her and then tell us why the relationship didn't work out and why you got out of it.

[John (Amanda's Ex-Boyfriend)]

All right? Well, I think first and foremost, you know, it was a long time ago. We were kind of young and that has a lot to do with it I think for me. Basically, you know, we started dating in college and she was, you know, we had a lot of fun. We hit it off. Excuse me. Obviously. And you know, just over time, I'd say about, I don't know, half a year into being together, you know, we were going out, we'd go to movies, we'd hang out with friends, we'd go to, you know, a bar every now and again. We, you know, parties. You know, she was, we had a lot of fun. And then about half a year into our relationship, she just kind of like, you know, wanted to be. Stay home a little bit more and she had an apartment just off campus and like, you know, she just wanted to be there and you know, watch a movie and she just wanted to stop wanting to go out even like, hey, let's go go to the diner and get some food. You know, not even that. She's like, nah, just I've got some sandwich here. And you know, just like she just got really kind of, I guess to me as a 21 year old, kind of like homebody ish. It felt like we were in our 30s all of a sudden and, or even older and I mean basically she just wanted to, you know, study and oh, she got. The main thing was that, I mean her excuse for all this was like, well, you know, we should, we should stay in because we have test next week and you know, we have to do well and get A's and if I don't get A's and I won't be, you know, I think she was pre law at the time. I'm not sure what ended up happening. But yeah, I mean she was just totally focused and I don't know, it's just kind of was boring for I think I was 20 when we were going out and I don't know, I was more into, you know, partying, you know, and going out with friends and you know, seeing what's out there and you know, it's exciting time. You have lots of energy and. Yeah, she just kind of went from early 20s to mid-30s in like a one month period.

[Host 1]

Initially, she was excited about going out. You guys were doing it up. But then about six months into it, that's when she got all studious and she's like, it's time to focus.

[John (Amanda's Ex-Boyfriend)]

Yeah, I mean, it was something like that. Yeah, six months. Yeah, something like that. I remember it was after the first semester and then all of a sudden it was like, boom, you know, buckle down time, buddy. And I was like, oh, I thought we were having fun. You know, I mean, we had fun for the first six months and then

[Host 1]

too serious, too fast.

[Commentator]

Well, did she let you, did she let you go out or did she make you a homebody? Homebody too?

[John (Amanda's Ex-Boyfriend)]

Well, it was kind of like if I wanted to hang out with her, which I did, then I had to stay home. So, you know, then after a couple months of that, you know, you're kind of like, well, you know, maybe I could, you know, do better and have a, you know, a little bit more of an exciting relationship than this is currently. Because as I said, it went from like, hey, we're young and fun and in our early 20s to, you know, we're 35 and have been married for eight years or, you know, or something like that is how it kind of felt.

[Host 2]

Which side of her do you think is the real her?

[John (Amanda's Ex-Boyfriend)]

I would guess the second side turned into. I mean, I. Because I mean, I know she was a very good student and you know, I mean, she's very ambitious and focused, which, you know, I'm not going to fault anybody for because, you know, you want to be successful, you. It's going to take focus. But for me, as just somebody who is young and looking to, you know, date and have fun and, you know, I thought she was vivacious, but you know, then that, that just kind of switched after a second and she turned into, I guess what she really wants to be, which is probably more of a career person or.

[Host 1]

Okay, it's not a crazy scenario.

[Host 3]

You know, she was selling in the beginning market. It's all marketing.

[Host 1]

You put the face on initially, you know, because you're all excited, so you're willing to sort of sacrifice self a little more because you really dig somebody and then inevitably you end up being who you are. And in her case, it was just a very serious person, very focused person, needed to graduate, needed to get in the workforce.

[Commentator]

You go from spray to sweatpants. So you go from looking hot to you Know, just getting comfortable.

[Host 1]

I'm just curious. Did you end up graduating?

[John (Amanda's Ex-Boyfriend)]

Not from that school, but eventually, yes. A little bit longer, maybe. If I would have stuck to her path, I would have graduated on time, but, you know. But no, she. I did. Yeah. I mean, we're. We're all, you know, I'm all. I'm all squared away, maybe at this point, but for, you know, for a man, I don't even. I haven't talked to her, and, I mean, I was actually really surprised to get a call from you guys.

[Host 1]

All right, so, I mean, this isn't a huge offense or anything like that. She was just, you know, she's focused and she put on one face to begin with, and then she became focused again, and you lost interest easy.

[John (Amanda's Ex-Boyfriend)]

Oh, yeah. Well, it didn't even. I mean, I don't. I mean, I don't know what she says about it, but I mean, it. It. To me, it didn't really even end that badly. It was just kind of an understanding, you know. To me, it didn't end badly. I don't know what she said about it, but, yeah, I mean, I would say that that's exactly what happened. And, you know, that's not the first person that that's ever happened with, you know?

[Host 3]

Do you miss her?

[John (Amanda's Ex-Boyfriend)]

Oh, no, no, not. I mean, you know, no. I mean, sometimes, you know, I look at old pictures from college and she'll be in when I'm like, oh, hey, that's my ex girlfriend, you know, like. But it's not like.

[Host 3]

Like, do you think about her? How often do you think about her?

[Host 1]

Like, when you're making love to your wife, maybe?

[John (Amanda's Ex-Boyfriend)]

Hey, I didn't know.

[Host 3]

Bert, what the hell is wrong with you? Why are you going down this road?

[Host 1]

I was just cutting Jeff off before he got there.

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[Host 1]

he didn't

[Host 3]

tell his wife, and he's. You know, there's a lot of words, and it's sometimes that.

[Host 1]

John, you're fine. You're in the clear, man. We got what we wanted. Thank you very much.

[Host 2]

Thank you for coming on.

[Host 1]

All right, talk to you later, man. Thank you.

[John (Amanda's Ex-Boyfriend)]

All right. Yeah, thanks. Good luck, guys.

[Host 1]

All right, so maybe that's the first piece of the puzzle right there. All right, That's a guy that she dated, 13, and she just wasn't into partying as much as he was. Although she sort of said that at first and showed that initially.

[Host 2]

Right.

[Host 1]

And then she just got focused and had to graduate.

[Host 2]

Not too crazy, Got more homebody. Ish.

[Commentator]

Just wanted to settle down faster maybe, but nothing wild and crazy.

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[John (Amanda's Ex-Boyfriend)]

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