Vault: All Of Her Exes Are Gay...Why?

Summary

The Bert Show – Vault: All Of Her Exes Are Gay...Why?

Date: January 20, 2026
Host: Pionaire Podcasting Team (Bert, Kristin, Abby, Cassie, Tommy, et al.)
Episode Theme:
This episode centers around a listener, Alyssa, who reveals that both of her serious boyfriends turned out to be gay. The cast and listeners discuss her experiences, why this may have happened, and how it speaks to broader themes of dating, sexuality, and self-discovery, especially in younger years.

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Episode Overview

Alyssa, a 21-year-old listener, calls in using a voice disguiser to share her unique relationship history: both of her two major boyfriends later came out as gay. The episode explores her story, the emotional implications, and the perspectives of hosts and other callers who have had similar experiences or insights. Humor and empathy drive the conversation, with a focus on understanding rather than judging.

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Key Discussion Points & Insights

1. Alyssa’s Story: Two Boyfriends, Both Came Out as Gay

• Alyssa nervously introduces her situation, noting, “Both guys have ended up being gay.” (00:33)
• First boyfriend: Dated from ages 14-17, described as “a little flamboyant,” but Alyssa was too “naïve” to recognize signs at the time. (00:43)
  • “He could bust a big Beyoncé moment.” – Alyssa (01:53)
  • Came out a year after their breakup.
• Second boyfriend: Met at 18, described as “very manly” and even a bit homophobic as a “cover.” (02:48, 03:46)
  • “He was a guy’s guy.” – Alyssa (03:25)
  • Relationship was serious: lived together, had promise rings. After breakup, he came out and introduced Alyssa to his new boyfriend. (04:25)
  • Both boyfriends admitted to knowing they were gay long before they met her. (04:54)

2. Host Reflections: It's Not Your Fault

• The hosts immediately reassure Alyssa that her experiences are not her fault, emphasizing that many go through similar situations.
  • “There’s no reason for you to be fearful that this will always happen... the older you get, the less you’ll run into this.” – Host (05:23)
• The conversation delves into how societal pressures, especially in youth, can lead closeted gay individuals to seek heterosexual relationships to “try to work it out.” (05:23–06:33)

3. Cheating, Honesty, and Responsibility

• Caller Brad relates, empathizing with Alyssa and questioning if her boyfriends cheated with men during their relationships. (06:45)
  • Hosts express doubt that Alyssa would know, and reinforce fidelity is about honesty, regardless of sexuality. (07:15–07:56)
  • “It’s cheating regardless of who you’re cheating with.” – Host (07:56)
• Another listener, Jennifer, calls sharing that both her ex-husband and a subsequent serious boyfriend later came out as gay. (08:22)

4. The “List” and Attractiveness Factors

• Hosts invite Alyssa to share her list of attributes for an ideal man.
  • Alyssa’s list: “Romantic, willing to have fun, able to settle, watch a movie, cuddle, hold me, a little sensitive, talk to me, carry on a good conversation.” (09:23)
  • The hosts joke, “I would suggest you to continue dating gay men.” (09:57)
• The discussion turns to whether Alyssa’s nurturing personality and openness might make gay men feel “safe” with her. (10:43)
  • “Maybe gay guys are drawn to me because I’m not judgmental... I’m very caring... so they can feel safe with me.” – Alyssa (10:43)

5. Emotional Safety & Attraction

• A host relates her own story of dating men before coming out and feeling more emotionally relaxed because “there wasn’t as much at risk” as there would have been with a woman she was truly attracted to. (11:23–12:29)
  • “Does that make sense?” – Host, checking in with Alyssa (12:29)
• The group suggests that these relationships are often rooted in emotional safety rather than sexual attraction.

6. Moving Forward, Advice for Alyssa

• The hosts assure Alyssa her experience is a “fluke,” not a pattern, highlighting that older, more self-aware partners are more honest.
  • “By the time I was 25, everything was said and done.” – Host (15:54)
• Suggestions range from changing the kind of traits she’s seeking to humorously speculating about “telltale” characteristics (e.g., “collection of Broadway musical CDs” or noticing nail polish colors) as jokes. (16:11–16:30)
• A recurring theme: as people age, “the more secure they are in themselves, the more honest they can be.” (05:23, 15:54)

7. Similar Stories from Listeners

• Amy calls in saying she dated four gay men in high school; again, these relationships were often about providing cover (“beard”) rather than intentional deception. (17:22)
• The show veers into high school band stereotypes as light banter, with the group acknowledging no real “type” can be identified.

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Notable Quotes & Memorable Moments

• “He could bust a big Beyoncé moment.”
  — Alyssa, on her first boyfriend. (01:53)

• “He was sort of a typical, stereotypical macho dude.”
  — Host, summarizing Alyssa's second boyfriend. (03:21)

• “He’s a homophobic gay guy.”
  — Host, on the second boyfriend's behavior. (03:46)

• “It’s cheating regardless of who you’re cheating with.”
  — Host, reinforcing the importance of honesty in relationships. (07:56)

• "I would suggest you to continue dating gay men."
  — Host, joking about Alyssa's list of ideal man traits. (09:57)

• "Maybe gay guys are drawn to me because I'm not judgmental... I'm very caring, very nurturing and stuff like that, and so they can feel safe with me."
  — Alyssa reflecting on why this keeps happening. (10:43)

• “By the time I was 25, everything was said and done.”
  — Host, on self-discovery and honesty increasing with age. (15:54)

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Key Segment Timestamps

• Alyssa’s introduction and first boyfriend story: 00:33–02:34
• Second boyfriend and the “cover” discussion: 02:48–04:54
• Reactions, broader context (honesty and age): 05:13–07:56
• Caller Jennifer’s similar experience: 08:25–08:40
• Alyssa’s “perfect man” list: 09:23–09:57
• Reasons why gay men might be drawn to Alyssa: 10:43–12:29
• Advice and wrap-up: 13:35–16:16
• More listener stories (Amy dating four gay men): 17:20–18:12

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Episode Tone & Language

The conversation flows naturally between empathy and playful banter, with hosts using self-deprecating humor and honest, sometimes raw, reflections about sexuality, adolescence, and relationship confusion. The show prioritizes a nonjudgmental, understanding tone throughout.

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Key Takeaways

• Alyssa’s experience, while rare, is shared by others.
• Adolescence is a time of confusion and self-discovery for many, contributing to such scenarios.
• It is not Alyssa’s “fault,” nor does it indicate a pattern that will persist.
• Emotional safety and openness can make some people natural confidantes or partners for those struggling with identity.
• With age comes self-awareness, and such situations become increasingly unlikely.
• The importance of honesty and empathy in all relationships is repeatedly underlined.

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For listeners who haven’t heard the episode:
This conversation offers comfort, camaraderie, and practical advice to anyone whose romantic history has involved similar surprises, while providing plenty of laughs and relatable insights along the way.

Transcript

[A]

The Bird show.

[B]

Okay, Jeff, we are gonna need the voice disguiser, and we are gonna call this Birchell listener Alyssa. Good morning, Alyssa.

[C]

Good morning.

[B]

How are you? A little nervous not to be nervous about. First, you're on the voice disguiser, and nobody can recognize your voice. And secondly, nobody's listening, so there you go.

[D]

Yeah, it's just us.

[C]

I wanted to say first thing, I love the show. Listen to it every morning.

[B]

Boy, now everybody's gonna know who you are.

[D]

Okay, what happened?

[E]

So what's going on, Alyssa?

[C]

Okay. I recently turned 21. Beginning of this year, and my two major relationships. Both guys have ended up being gay.

[D]

Mm.

[C]

And the first guy. Okay, it should have been a given. He was a little flamboyant, but I was a little naive at the time. Should have seen it, but didn't.

[E]

How old were you when you dated him?

[C]

Between the ages of 14 and, like, 17, I think.

[E]

Okay, so this was your, like, major high school love.

[C]

Yeah.

[B]

Okay. And the characteristics were. Flamboyance. What else?

[C]

Slight flamboyant. Not all the time. It was very hidden, sometimes.

[B]

Subtle flamboyance.

[F]

Yeah, he had a subtle flamboyance that I found charming.

[B]

That's my blog. Subtle flamboyance.

[C]

All right, the second guy met him the age of 18, like, right before we graduated.

[B]

Hold on one sec.

[F]

Let's.

[B]

Let's back up to guy number one, because we're trying to. We're trying to build a case here. Okay, so slight. Slight flamboyance. What else about him? Because you said I should have been able to spot these things.

[C]

Honestly, like, even looking back on it now, I really just. The flamboyance is a big thing. I really can't think of much of anything else.

[B]

Okay, let me just throw it. Flamboyance. Do you mean, like, feminine? Do you mean.

[C]

Yeah, he'd have his moments where, you know, he could bust a big Beyonce moment.

[B]

A big what?

[D]

A Beyonce moment. He could bust into a Beyonce moment.

[B]

Oh, Beyonce moment.

[D]

Many high school boys do that.

[B]

Okay, so. All right. Gotcha. Bit of a drama queen.

[C]

Yeah, a little. Yeah.

[B]

All right.

[E]

Okay.

[C]

But, I mean, it's not like he was the one causing all the drama. It's just the people he chose to be around, I think. So it wasn't ever him actually drawing any attention to himself.

[B]

Okay. And this guy you dated again, from you were 14 to how old?

[C]

To about 16 or 17. So it was on and off. I mean, it wasn't a continuous thing.

[B]

And when you break up with him or he breaks up with you at 16, does he tell you at that point, look, here's really what's going on, or do you find out years later?

[C]

No, it still took, like, about another year for him to actually say anything to me.

[B]

Okay. Guy number two.

[C]

Okay. Met him right before I graduated, and he was a total opposite. Even my friends kind of, you know, they didn't notice anything. He's very manly. When he got around my first ex, he knew that this guy was gay. And he got very, oh, you know, I'm tough, I'm hard, you know, and he was the total opposite of the first guy. So I thought I was safe. And no flamboyance, Nothing that I could see, Nothing at all.

[E]

So he was sort of typical, stereotypical macho dude.

[C]

Yeah, yeah, a guy's guy.

[D]

Now, did he talk. Did he talk bad about the first guy, or did he just know he was gay?

[C]

He knew he was gay. And, like, the first time I got him in the car together, honestly, he got all tough, you know, tried to be all macho and stuff. And he would tell me, you know, he was a little, you know, I guess you could say homophobe, you know.

[F]

He'S a homophobic gay guy.

[D]

It was a cover.

[C]

It was a cover. Yeah, it was a cover. But I believed it.

[B]

He was a stealth gay guy because.

[D]

Yeah, I remember a comment. I honestly made this comment in high school. Why do they want something they've already got? And I had already slept with a woman at that point, but it was a cover.

[B]

All right, so this, what, his macho, macho thing was just a cover? Just a beard.

[D]

Right.

[B]

All right, so you're going out with him from how old to how old?

[C]

18 till 20.

[D]

Okay.

[B]

And same question. When you break up, he tells you at that point, this is the reason why I'm breaking up. Or do you find out years later?

[C]

Well, he and I got very, very serious. We were together for, like, two and a half years. We lived together for a year. We're very, very serious. Everybody thought we were about to get married. Promise rings were, you know, in hand. We broke up, and he turned around and told me, like, a month later, hey, I'm gay and this is my new boyfriend.

[B]

And he didn't say this gay thing happened over the last 30 days. He's known for years.

[C]

No, they both have admitted to me that it was long before they even met me. Like, my second boyfriend said he can remember memories back to being, like, five years old, having thoughts about being with a boy instead of a girl. These were never Shared with me.

[B]

This is really kind of a chance circumstance here because, I mean, there might be some women that have one story in their past, but you've had two serious boyfriends, and both guys have been gay. Melissa's looking at me well.

[D]

And also the first thing I want to say is that there's no reason for you to be fearful that this will always happen. Because the first thing when I heard your age and heard when this happened, even though I know it's traumatic for you at this point, but I really think the older you get, the less you'll run into this. Because, you know, this is just an age in which people don't feel comfortable with themselves. Like, I think these guys honestly tried to have a relationship with you. I think these guys honestly wanted to work it out with you, but they couldn't escape who they really were, and that's the age that they were. So I would not. I mean, I know it's got to be tough for you, especially that second one, but it's not. This is probably not going to happen to you again. Because men and women, the older they get, the more secure they are in themselves, the more honest they can be with themselves and everybody else. Because I dated guys in high school and college, and I really gave them a shot. I really wanted to fall in love with them, and I really wanted to make it work with them because I didn't want to be who I knew I was. And I'm sure those guys, in hindsight, like, I didn't go and tell them, like, they probably have found out by this point and are completely confused, but it had nothing to do with them. You know, I tried. I didn't cheat on them. I did not sleep with the woman behind their back. Nothing like that. I really. And I think the same with these guys. I think they really honestly tried, you know?

[C]

Yeah.

[B]

Hey, I want to. I want to put you on hold for just one second because Brad is calling up with a goodwill hunting moment. He's going to tell you it's not your fault. Hold on one second, okay?

[C]

Okay.

[B]

Good morning, Brad. You're on the Burt Show. Hi.

[A]

Hey, what's up? How you doing?

[B]

What's going on?

[A]

Not much. I just want to tell her that, like, you know, it's not your fault that this has happened before, because this has happened, like, to plenty of girls out there before. I mean, I've done it myself. I do have a question for you. Do you think he, like, they cheated on you while they. With another guy while they were dating? You that's my, like, one question for you.

[B]

She's not on with you because she's has to be on the voice disguiser. So we'll ask her that as soon as we put her back on.

[A]

Okay?

[D]

I mean, I doubt she knows. I mean, because she had no clue anything was going on while she's dating them, you know, but we will ask her, you know.

[B]

Well, what will that say to you? Depending on her answer.

[A]

I mean, I probably. They probably did. I mean, I really think they did. I mean, if he broke up with her and then a month later tells her that he's gay and he has a new boyfriend, I mean, he. It's obviously that, you know, he cheated on her. I mean, it's pretty obvious.

[F]

But what difference does that make?

[A]

It doesn't make. It doesn't make any difference. And it's not his fault. But I mean, it's just. I mean. I mean, I can understand what she's been through. I mean, I've done it before, and it's just. It's just. It's a terrible thing that's happened to her.

[D]

I mean, I hope not. I mean, men and women are different. I mean, guys. He may have cheated on her. I just know that I never cheated on the guys I was with because it's still cheating. I mean, it's cheating regardless of who you're cheating with. And even though I would have attraction and feelings for other women, I mean, I gave it my all and had nothing to do with the guys, the reason that I am who I am. So I do think that his point is valid. Alyssa, this has nothing to do with her.

[B]

Jennifer, good morning. You're on all the hits. Q100. Hi.

[G]

I just want to let you know that I can very much empathize with that other caller. I was actually married to a man who turned out to be gay. And then just a year ago, I was dating a fellow that after four months of serious dating, found out he.

[C]

Was gay as well.

[D]

What. I'm curious to go over Alyssa's list because she had made a list of what she finds to be the perfect man. And I think there may be some things. And again, this is not against straight guys, but I do think there's some things that might be a few clues.

[B]

Hey, Alyssa, you're back on the voice disguiser.

[C]

Hi.

[B]

Melissa wants to hear that list of characteristics.

[D]

And before I. Before you give the list of characters, I do want to say to the guy that married the woman, like, I do believe that you have. It's tough and it's hell. But you have a responsibility the older you get, too be secure. And to be honest with people, I would never bring somebody into a marriage knowing I was lying to them the whole time, so. But I think Alyssa's is different because these were teenagers. So, anyway, Alyssa, your list of the perfect man.

[C]

Oh, gosh. Romance has to be in there. He's got to be romantic. I mean, he's got to be willing to have fun. But at the end of the day, I want a guy that'll be able to settle down with me and watch a movie. God, I don't want to say the word cuddle, but, you know, hold me and stuff like that. He's got to be a little sensitive. I mean, he's got to be able to talk to me and carry on a good conversation instead of just, you know, blowing off my feelings and stuff.

[F]

And I like the fact that he can do my hair. I like the fact that he does my hair before he goes out every time.

[B]

I would suggest you to continue dating gay men.

[D]

I have to be on this.

[F]

An impeccable dresser. He has to work out all the time. No body hair. None.

[C]

No. Nothing like that.

[D]

No.

[C]

I'm not even asking for a good jump, sir.

[B]

You know what? When I was looking at your list yesterday, this is another debate for another time. But I think that we all have, like, this list in our minds of who the perfect person is. And after a while, you just start, like, one by one, going, yeah, that one's not going to happen. Let's go ahead. Put that one aside and that one aside. But you know what? They've got this one thing, so I'm gonna go ahead and run with it.

[C]

Well, I mean, after the breakup and everything, and actually meeting my ex's first boyfriend, he actually, you know, I had told him, this has happened twice to me now. This is a little, you know, scary, and I. I'm scared to venture out and. Because I'm afraid this is gonna happen again. And he actually said it was the type of guy that I was looking for. And then he proceeded to say that it's also the type of person that I am, that maybe gay guys are drawn to me because I'm not judgmental quickly. You know, I'm very caring, very nurturing and stuff like that, and so they can feel safe with me.

[F]

What if you look like a man?

[D]

You know, I was thinking about this yesterday because we talked about how we were going to talk to you, and I was trying to think about, like, my high school Boyfriend who again, it was on and off relationship. We dated mainly my senior year in high school. And I truly cared for him. I mean he fantastic man and. But I did realize that there was such an attraction to me from him. And part of me wondered also because I really, to me, in my heart, there wasn't as much at risk with him because I was not as attracted to him as I've been with women. So I was a lot more comfortable with him. I gave him a lot more of a challenge. I spoke my mind. I felt like, because I was so relaxed with him that I just. He was just drawn to me even more because I wasn't the type of woman that. Because he was in my life, all of a sudden I dumbed myself down. I changed everything in my life for him. I did all, you know, and I just felt like being at ease with him caused him to be more attracted to me. And I'm wondering with you, is that the same thing like these guys? I mean, it has nothing again to do with you, but you know, there's not as much at risk to them emotionally with you as there would be to a guy. Does that make sense?

[C]

Yeah.

[B]

That's heavy.

[D]

Yeah. And I just wonder if that's, you know, that's why you were so attracted to these guys, because they're are different, because they treat you differently.

[B]

That's like a damn Dr. Phil moment right there.

[F]

Well, you know, I think you had it in you.

[D]

I've had to deal with this quite a bit. So I've analyzed a bit. But yeah.

[B]

My response is going to be way easier than that. I think if you just take the hold me part out of your equation, you're going to find it way, way, way easier to find a guy that you can be compatible with, cuddle out of the picture, you'll find the right man.

[F]

I don't know.

[E]

I picture Jeff Dollar to be a cuddler.

[D]

Yeah, he's like a big bear.

[E]

He's a snuggler.

[D]

Little snuggle bear.

[E]

You like to snuggle, don't you?

[F]

Hibernator.

[E]

You guys do the little spoon action.

[D]

Yeah, you're a spooner. And I will say this also, Alyssa, I, the guy that I dated, my. The one serious boyfriend I had, I'd feel. To this day, I feel guilty. To this day I feel bad because I wasn't strong enough at the time to know who I was. And I just feel. I feel like I did lie to him. And I, and I, yeah, I will always feel bad because what do you.

[E]

Think Alyssa has to do differently as she moves forward? I mean, that's sort of what you're looking for, right? You're. I'm 21. I've dated two guys that ended up being gay. My two serious relationships. I was loved with somebody. So moving forward, how do you not make that mistake again?

[F]

Well, I'd stop trying to pick up guys at the outright bookstore.

[A]

Like, maybe I need to move into.

[D]

You know, I love how Jeff knows all these gay places, too. Okay, so just. I'm hearing you, Jeff. Alyssa, I just think that if a guy is your. Is. Does the same things. Your best friend. Like, if he feels like your best friend, you can tell him anything, and he can sit and watch a movie with you, and you can sit and talk about the most emotional, intimate things. I just don't think that's something that. I think that's where you're.

[B]

That's a fine line.

[D]

You're being lured into something that I think is. I don't know. I think that's what she's attracted to somebody that ends up being her best friend. And then it evolves.

[B]

What a dangerous message to send, though. That's like saying, okay, if a guy is willing to be your best friend, then he must be gay.

[D]

But did you hear what I said, though? Did you sit with your girlfriends that were your best friends, that you were just waiting to have sex with them and sit and talk for hours about emotional issues and stuff?

[B]

Not emotional issues, but, yeah, I was willing to sit and talk about anything they wanted to talk about in order to have sex.

[E]

What if she was up front about it? Like, what if she started dating a guy for, like, a month and, like, say, you're the next guy that starts dating Alyssa? What if she says to you, listen, I gotta be upfront with you about my past? She shouldn't do that.

[F]

No, Jeff.

[B]

Jeff, you want to take this one?

[F]

No, no. Imagine if you're dating a guy and you're two months into. He goes, look, this is gonna sound like a weird question, but I've kind of had a weird past. Are you a lesbian? Like, how insulted would you be?

[E]

Well, I don't think. Insulted. I don't know. I'm just trying to, like, help her for her future relationships. And I'm wondering if it's something she's struggling with, if she would bring it up.

[B]

Because I think it's a fluke, man. I think it's. I think it's a fluke.

[D]

Alyssa. Did these relationships with these two guys just all of A sudden fall into place and you're best friends, watching movies, doing all this stuff, or did you have to work at it?

[C]

Seriously, the first one, I was best friends with him. We were so comfortable with each other for, like, a whole year before we started dating. The second guy, he pursued me at prom and stuff. And it did take work because he and I were just, personality wise, we were two different people. But it did take work, but.

[D]

Well, just. Yeah. My advice is just the older you get, the less you're gonna have to deal with this. Number one. Because, you know, by the time I was 25, everything was said and done. And also, if they have any kind of, like, Broadway musical CDs in their collection, then, you know, sorry, guys.

[B]

Listen, we gotta run. We gotta move on for a couple more calls, and then we're gonna move on. All right. Thank you for calling.

[C]

Thank you.

[B]

Bye. Bye.

[F]

Like, here, One way to tell is to, like, put two different, you know, now colors on, you know, your opposite hands like that are in the same family of red, and see if he notices. Oh, I don't know if you notice this, but that's candy apple, and that's, you know, red cherry.

[B]

Well, Jen Hobby proved to me today that she thinks I'm gay because she asked me if I noticed the new highlights in her hair. So. Thank you. Hi.

[D]

Did he.

[E]

No.

[D]

Well, then you're straight.

[B]

Well, I can't see up that high.

[D]

If you were gay, you would have noticed.

[B]

Louis. Good morning.

[D]

Good morning.

[B]

Interesting theory. What's up?

[H]

Well, this is the quickest way to break up with somebody. You tell them that you're okay and it's a lie and there's no regrets and keep going with your life.

[B]

Yeah, I don't think that's the case. What he's saying is he's broken up with women before and just said, look, I'm gay.

[D]

Well, now, don't do that to us.

[B]

Just to get out of the way.

[F]

I can never hear that accent without thinking.

[D]

I mean, seriously, it is. It is tough. I mean, I. Again, I sympathize with the guys. I sympathize with Alyssa, but the guy. I mean, this is. It's not funny. It's not a joke. So I hate for straight guys to use that as an excuse.

[B]

I said to Alyssa, you know, she's dated two. Two gay guys. And I said, what a fluke that is. That's never gonna happen again. Amy.

[C]

Yes, Go ahead.

[I]

In high school, I had actually four boyfriends who ended up being gay, and they were dating me. To cover up the fact that they were gay.

[B]

So were they, like, passing, like, secret information onto each other, going, hey, this is a good girl? That could be.

[E]

She's a great beard.

[B]

Yeah, she's a great beard. You were the beard girl for four different guys?

[I]

Well, the first guy I had actually known since I was, like, 10, and we dated for about three years.

[D]

Again, this is teenage stories. I just want. Were any of them in the band? I'm just curious. I'm sorry, band guys. But seriously.

[I]

Yeah, actually, they were all in band. We were all in the band class together.

[B]

Now, what are you saying, Melissa?

[D]

I'm not saying. I just know. No, I'm not saying I asked. Only because in my high school. Because when you're gay in high school, you know every other gay person in that high school. And I know some guys in high school that had drama and it ended up being in that community.

[B]

Drama or band?

[D]

Band.

[B]

Band.

[D]

Okay, I'm not saying guys in band are gay. I'm not saying that.

[F]

Just the ones playing the flute.

[D]

But I'm saying women in band, if you're dating all the guys in the band. I'm just saying.

[E]

One time at band camp.

[D]

Sorry, band guys, but I'm just saying.

[A]

The bird show.