Vault: This Guy Is Convinced These Women Are Desperate

Summary

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The Bert Show – Vault: This Guy Is Convinced These Women Are Desperate

Date: March 17, 2026
Main Theme:
The episode revisits the ongoing saga of Trey, a long-time friend of the show, who, after years of joking about not finding "the one," accepted a challenge to get married by a certain deadline. The discussion humorously and honestly explores dating pressures, cultural expectations around marriage, and the experiences of singles in their 30s and 40s—especially the stigma attached to being unmarried at a certain age. The team gets real about love, urgency, social expectations, and the madness of orchestrated relationships.

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1. [01:00] Background: The Marriage Bet

• Burt resets the context—every year, Trey laments his single status, so his proactive friend Joel took matters into his own hands by booking wedding venues and rallying the show behind Trey's quest for a wife.
• Joel: "I've done everything I can, Burt. My friend's a loser." (01:48)
• The show then orchestrates dates for Trey, involving the audience and even Trey's mom, leading to an avalanche of attention and emails.

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2. [02:27] The Challenge & Social Pressure

• Joel’s “marriage challenge” is both a joke and social experiment, putting real pressure on Trey to meet the deadline.
• Trey admits he’s told everyone for years “I’m getting married next year,” pushing the whole event further as an ongoing bit.

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3. [03:57] Opinions on Marriage: Stigma and Skepticism

• Trey shares that being public with his quest for a spouse has led to endless unsolicited advice and jaded opinions on marriage.
  • Trey: "Every human being I've met in a public setting has given me their opinion on marriage." (03:57)
• Many people counsel him to avoid a hasty marriage, sharing their dissatisfaction with the institution.
  • Trey: “It’s amazing the amount of people that are unhappy right now in their marriage.” (04:30)

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4. [04:46] Age, Singleness & Judgment

• Burt and Trey debate the stigma of being unmarried past your early 30s or 40s, revealing the assumptions people make.
  • Trey: “If I get married and divorced, and then I'm 40, 41, 45 with a divorce, I look less like a psycho than I do if I'm 40, 45, and have never been married.” (05:21)
• The group agrees similar judgments go for both men and women: there’s an ingrained societal suspicion around long-term singles.

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5. [06:40] Are the 'Candidates' In It for Marriage or for Trey?

• Trey confides he feels that several of the women interested in the marriage challenge are more invested in getting married itself than in him as a person.
  • Trey: “After the second or third date, I could see these dependency issues... they just want to be married. That is their whole goal.” (12:32)
• This pattern is paralleled with stories about both genders feeling the heat to 'pair up,' especially in more traditional cultures.

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6. [08:03] What Married & Single Friends Say

• Trey and Joel relay what they've heard from people:
  • Married guys in bars usually sum it up as: “You’re crazy.” (08:18)
  • Married women, and people who’ve been through the institution, want to detail their mixed or negative experiences.
  • Many reveal they’re staying together “for the kids,” or are going through the motions despite dissatisfaction.

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7. [09:37] Listener Calls: The Other Side of Singleness

• Mary, a happy single woman at 43, calls in to reject the idea that being unmarried equals unhappiness.
  • Mary: “I’d rather be alone than with a horrible relationship.” (09:52)
• The hosts note that judgment still remains, regardless of personal satisfaction.

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8. [10:51] The Reality of the Dating Experiment

• Despite a flood of emails, Trey only went on about two serious dates, though he met around 25 people in person (11:01).
• The experience, he admits, was “overwhelming...kind of brutal,” with most dates feeling forced or unfulfilling after initial excitement.
• Trey feels both bombarded and disillusioned with the process, leaning into recluse behavior as the experience soured him on dating.

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9. [13:16] Desperation vs. Competition

• A second Mary calls with insight: “If he wants to get married that badly, you know, I bet the people that are going to contact him are the ones that are so desperate to get married.”
  • She points out that participating in such a contest may attract those more interested in “winning” or just getting married, rather than a true connection. (14:28)
• Trey concurs, breaking down the interested women into “desperate” and “competitive” types.
  • Trey: “Half the people that contacted me were desperate...the other half were competitive. It’s like The Bachelor.” (15:26)

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10. [16:19] Will Trey Go Through With It? Commitment Phobia vs. A Man of His Word

• The hosts press Trey: Are you still going to get married for the sake of it?
  • Trey: “I wouldn’t bet that I’m getting married to somebody I love. I might still get married just to get married because I said I was going to get married.” (16:19)
  • The panel advises against marrying just for the story or to check a box.
• In true Bert Show fashion, the segment closes with playful skepticism about whether Trey will actually keep his word, or if the whole episode is an elaborate running joke.

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11. [17:24] Conclusion & Takeaway

• The show summarizes — Trey's mission hasn't found the magic, most potential matches seemed more eager for marriage itself than for him, and the looming “wedding” date is more a product of social pressure and radio antics than authentic romance.
• Burt: “It doesn't look like there's anybody that he's very excited about marrying, but the marriage still may be on just because he told everybody he would do it.” (17:24)

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Notable Quotes & Memorable Moments

• Joel: "I've done everything I can, Burt. My friend's a loser." (01:48)
• Trey: "Every human being I've met in a public setting has given me their opinion on marriage." (03:57)
• Trey: "It’s amazing the amount of people that are unhappy right now in their marriage." (04:30)
• Trey: “If I get married and divorced...I look less like a psycho than I do if I’m 40, 45, and have never been married.” (05:21)
• Mary (caller): “I’d rather be alone than with a horrible relationship.” (09:52)
• Trey: “After the second or third date, I could see these dependency issues...they just want to be married. That is their whole goal.” (12:32)
• Trey: “Half the people that contacted me were desperate...the other half were competitive. It’s like The Bachelor.” (15:26)
• Trey: “I might still get married just to get married because I said I was going to get married.” (16:19)

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Key Timestamps

• [01:00] – The history of Trey’s marriage “challenge”
• [03:57] – Trey shares how public attention changed his view on marriage
• [04:46] – Societal judgment on singles in their 30s and 40s
• [08:03] – What married & single friends really say
• [09:37] – Listener Mary calls with the single perspective
• [10:51] – Trey’s dating stats and emotional fallout
• [13:16] – Are participants desperate or competitive?
• [16:19] – Would Trey marry for the story?
• [17:24] – Final summary: no magic match (yet), just lots of social pressure

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Tone and Takeaway

With characteristic self-deprecation and honesty, The Bert Show explores the absurdities and realities of modern dating and marriage. The hosts and callers bring humor, skepticism, and candid reflections to the universal questions: Does not being married mean you’ve failed? Why is there so much pressure—and what happens when you make marriage a contest? If you ever wondered what might happen if your love life became a radio bit, this episode is an entertaining, empathic answer.

Transcript

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[Burt]

games the first show. Well, they are back. Hello, boy.

[Trey]

Morning.

[Burt]

Good morning. How are you, Joel?

[Joel]

I'm fantastic. How are you?

[Burt]

Are you Trey?

[Trey]

I'm doing well, thanks for asking. How are you? Happy New Year to you.

[Simply Business Announcer]

To you as well.

[Burt]

You seem very cheery today. Very cheery today.

[Trey]

We have to be cheery. It's a new year.

[Wendy]

Are you engaged?

[Burt]

Is it because you're in love?

[Trey]

I am not engaged yet.

[Unidentified Male Commentator]

You got a week and a half, so you're all right.

[Trey]

I've got 13 days, so we've got plenty of time. We're gonna crack down here pretty soon.

[Burt]

Let's just reset this here real quick. Let's reset this real quick. It was Joel. This was Joel's idea. The best friend's idea. And each and every year, Trey's complaining that he doesn't have a woman and he's not married. So the best friend, Joel, got proactive and tell him what the plan was.

[Joel]

I've done everything I can, Burt. My friend's a loser.

[Burt]

You don't have a lot to work with.

[Joel]

You know, I have had this conversation. You know, I. We do stupid stuff all the time. So I came to Trey and was like, all right, you know what? We're gonna try something else this year. Every year, he's come to me and said, I'm getting married. I'm getting married. So I got a little bit proactive, sent out some save the date information, reserved some hotel rooms, and then when

[Unidentified Male Commentator]

put a deposit down on those rooms,

[Joel]

I put A deposit down on Trey and one of our other buddies rooms.

[Unidentified Male Commentator]

So the two of you will get married if nobody else.

[Wendy]

Which room's the honeymoon gonna be in?

[Joel]

We decided the one with a heart shaped tub. Love it. But no. We basically kind of put a little bit of meat behind a challenge to Trey and said, hey, you know, you're gonna have to get married January 17, 2009. And so I threw the challenge out to him. He said, all right, let's do that. That sounds fun. And so then, as the story goes, we brought it to you and you decided that maybe this could get a little bit more steam behind it if we did on the radio. And then it helped. He got a lot of dates out of it, and then he's a complete loser and won't follow through with it.

[Burt]

Now we got it. We did. We got a ton of emails.

[Joel]

Yes.

[Burt]

And we set you up.

[Unidentified Female Commentator]

Had your mom in here.

[Burt]

Had your mom in here and everything. Had them all lined up.

[Trey]

And, you know, I want to tell Joel exactly what I told him last year. I'm getting married next year. So, I mean, that's. Let's not question the fact here, you know, like I told him last year, I'll get married next year, so everything's fine.

[Burt]

So it doesn't look like it's gonna happen now in Vegas.

[Trey]

Well, it doesn't look like it's gonna happen, but we've learned something. I'm not ruling it out. I still have a flight reserved on my SkyMiles, which, you know, if anybody with SkyMiles, you can cancel that, but I'm telling people that I'm not completely ruling it out because I've got some things going on in my head, but I'm not in love right now.

[Unidentified Male Commentator]

Are you?

[Burt]

What?

[Joel]

Wendy, tell them what you told me this morning. Trey, what are your thoughts on marriage?

[Trey]

When I started this, Since I've started this, every human being I've met in a public setting has given me their opinion on marriage.

[Burt]

Oh, yeah.

[Trey]

Oh, yeah.

[Unidentified Male Commentator]

That's gotta be fun.

[Trey]

Literally, every conversation I've been in, from relatives to the people that I meet through work and in the bars, people find out I'm doing this, and they heard about me on the birth show, so they tell me what they think about marriage. So to be completely honest, I'm a little jaded about the whole concept of marriage.

[Burt]

So they're not endorsing marriage. What they're saying is, be sure you know what you're doing here because it's not a great institution.

[Trey]

Save yourself fool, save yourself. Yeah, it's just. It's amazing the amount of people that are unhappy right now in their marriage.

[Unidentified Male Commentator]

It's great.

[Wendy]

Trey's just a commitment phobe. He's gonna be like George Clooney. You're not gonna ever be him. I know.

[Burt]

Here's the thing. How old are you now, Trey?

[Trey]

I am 26.

[Burt]

How old are you now, Trey?

[Trey]

I am 35.

[Burt]

Okay, here's the thing. And it's sort of. I think that there is this misconception, like, if you're 32, 33, 34, 35, 40, 42, or whatever, and you're not married, all of a sudden you're thinking, okay, maybe I'm not a great. Maybe I'm doing something wrong here. Well, the truth is, maybe you just haven't found the right person yet. Maybe there's nothing wrong with you at all in other people's cases. Maybe there's nothing wrong with them and they just haven't found the right person yet. So why does it have to be that there's something wrong with you?

[Trey]

I agree. And the interesting thing is, if, you know, we're doing. We did this whole piece in the south, which is more. Everybody's gotta be married when they're 21. If we did this in New York City or in la, I guarantee it. Well, LA would be a little weird, but New York or up north, we probably would have had a different result. Because, like, you're saying, people do expect. You know, one of my thoughts going into this thing was I'll get married. Because if I get married and divorced, and then I'm 40, 41, 45 with a divorce, I look less like a psycho than I do if I'm 40, 45, and have never been married.

[Burt]

That is true. I think that is true. Don't you guys agree?

[Unidentified Female Commentator]

Absolutely.

[Unidentified Male Commentator]

Barely. But yeah.

[Unidentified Female Commentator]

Yeah, I agree with that. If you're a man who's in your mid-40s or near 50, and you've never been married, a woman's gonna look at you. I mean, everybody's trying to be nice, but, yeah, women will judge you for that.

[Burt]

And it goes with women. Also, if you've never been married and you're in your late 30s or early 40s, guys are thinking, well, there's got to be a reason for that. But if you've been. If you've tried it once and you failed, all of a sudden you have more credibility.

[Trey]

Yep.

[Burt]

That didn't make any sense. So you said you have some things floating around. So the possibility is sort of there. It sounds pretty slim, right? But are there, is there at least one woman that you would seriously like if a gun was to your head right now? Is there one of the women that you're dating right now you'd say, you know what? I think I can make it work.

[Joel]

I.

[Trey]

There's a couple people I could marry. I'm pretty sure that would.

[Unidentified Male Commentator]

Would they marry you?

[Trey]

Yes, they would do it.

[Unidentified Male Commentator]

There's a bold statement right there.

[Trey]

I think, you know, this is my gut feeling. It could be completely wrong, but if, if it came down to it and there was a gun to my head, I think I could, could get a couple of people to say, if I

[Unidentified Male Commentator]

got him drunk, I could make it work.

[Burt]

Wendy, you haven't bought into this since day one. You, you said since day one he was never going to get married.

[Wendy]

I just don't think Trey can commit to anybody. Even if you like somebody, I don't think you could comm. Like even two months.

[Trey]

Why do you think that?

[Wendy]

Have you committed to anybody in two months? In a year?

[Trey]

No. See, but, but still, I've been dating lots of people. In this period of time that you've kind of seen me operate.

[Burt]

Have you ever been in a long term relationship?

[Trey]

I have. I have been in a three year relationship. Thank you very much.

[Wendy]

Congratulations.

[Trey]

That ended awfully. And then I've been in a. No, it didn't happen.

[Unidentified Male Commentator]

How long have you and Joel been dating?

[Trey]

Joel and I have been together for about two years now, off and on.

[Wendy]

Do you guys need to break up in order to find a girl?

[Joel]

I haven't any trouble.

[Trey]

Speaking of marriage, I was gonna say,

[Unidentified Male Commentator]

has this gotten you any closer to,

[Joel]

I mean, to tag on what Trey's saying? You know, this has gotten lots of reasons not to. After all this.

[Burt]

What are you hearing? Like, I'm curious. First of all, half the guys coming up to you, I'm assuming, is when you're either doing gigs in bars or you're at bars. So they're hammered, right? So the guys that are approaching you that are married in bars, what are they telling you about marriage? What's the thing that scares you the most?

[Joel]

Couple of things.

[Trey]

The guys are just like, you're crazy. And that's it. That's in the conversation. The girls, however, want to have the 30 minute to an hour conversation about exactly how they feel about marriage and this and that. And what I've found is everybody or a lot of people are together in their marriage just for the kids, which is, I guess this is people that have been married for a while, and it's just kind of depressing, actually. You know, it's not. It's like people aren't in for each other. They're in for the kids or they're getting out or they're cheating or. It's just unbelievable what's going on out there.

[Unidentified Male Commentator]

Well, this is taking a happy turn.

[Burt]

I mean, it's taking an honest turn. I mean, I think I saw. I saw a survey a couple of weeks ago that was done with people that were married over seven years and asked them if they would marry the same person over again. And 75% of the respondents said, no way. I believe that after seven years of marriage, so.

[Unidentified Male Commentator]

And 20% of the remaining ones were scared that their significant other was going to find out about the survey, so they lied.

[Trey]

But, you know, it's true. It's like. Like I said, I've been bombarded by people that want to talk about marriage and what they think, and it's not a positive thing. Maybe I'm in the wrong place. I don't know. It's weird out there.

[Burt]

Good morning, arlene. You're on Q100.

[Caller Mary]

Hey, I just wanted to make a comment about you saying if you're in your 40s and you're a woman, you've never been married. People look at you. I'm sure that's true, but I'm 43 and I've never been married, and I'm happy by myself.

[Burt]

Cool.

[Caller Mary]

I'd rather be. I'd rather be alone than with a horrible relationship.

[Burt]

I could not agree more.

[Unidentified Male Commentator]

I don't think anybody.

[Burt]

There are so many people that are with somebody for the wrong reasons, then. Then to be by yourself for the ride.

[Caller Mary]

There are plenty of them that got married for the wrong reasons, and I would never want to do something like that. So I think I'm better off.

[Unidentified Male Commentator]

Well, no, I don't think anybody's questioning the happiness of the person who chose to stay single. I think the reality of it is there's a stigma attached to that. So while you're completely happy, everyone thinks you're a spinster.

[Unidentified Female Commentator]

Spinster.

[Burt]

I wonder if there's anybody that's single, like in their late 30s, early 40s, that lies to other people, that has been single their whole life and lies and said, yeah, I've been divorced.

[Unidentified Female Commentator]

I'm sure. Depends. It depends. And I think that people who are single, like, we talk about it, but I think if anybody in your circles were in their 40s and never been married and were single, you're the friends are the first ones to try to hook you up with somebody or, oh, I got somebody you need to meet. And, you know, and people just don't want to be, I don't know, coupled if they. If they've chosen not to be.

[Burt]

So how many actual dates have you gone on in this whole process? Because we're talking about four or five months now. So how many dates we talking about?

[Trey]

Probably two. Two dates. Two dates, yeah.

[Burt]

So you've really committed.

[Trey]

We've got six emails and we went on two dates. It was awesome. No, I went on. Probably met personally, met probably 25 people. And to be honest, it was a little overwhelming when we started on the radio, I was getting bombarded by emails, so it was hard to meet these people. Plus, every single one of these dates was a blind date. And, you know, those can be brutal, like I've said on the radio before. So it just got kind of taxing and. And depressive, actually. So I didn't go on as many as I could have. I kind of became a recluse a little bit, I think, towards the end. And, you know, it's just, you go on one of these and you meet and then you talk for an hour, and it's interesting to talk to the person for 20, 30 minutes, but then it just drags and drags and do that over and over and over. It's kind of brutal.

[Unidentified Male Commentator]

So what the Bird show's involvement has done to you has made you one of those contracts who don't leave their house and also has soured you to toward the future of life with one person.

[Burt]

Well, here's what. Well, here's really what we've done here is there isn't over the last couple of months, there is no alternative. Because what you're saying is all your married friends are telling you marriage sucks, and you've been dating all these women for the last couple of months. And the single life sucks, too.

[Trey]

I like the single life. You know, I don't have. I enjoy my place right now, but

[Unidentified Male Commentator]

Joel would just get off my back.

[Trey]

Sorry. But I. The girl. It's interesting. A lot of the people that contacted me and you guys know this from the early days were very dependent individuals. You know, I had a lot of people that. I showed you some emails where, hey, I'll marry you. Oh, okay. Kind of weird. So some of the girls that I met and that I was attracted to and, you know, we kind of meshed a little bit after the second or third date. I could see these dependency Issues. You know, we find out about their past and where they're coming from, and it was like, they just want to be married. That is their whole goal. So then I was thinking, you know, are they really into me, or are they just into this whole concept, which is kind of bad news? So that ruined me a little bit, too.

[Burt]

This is a little bit like Kimberly, who we've been talking to the last couple of weeks also. She just wants to be married so badly, it's stuck in her head.

[Unidentified Female Commentator]

But they probably felt they were safe here because you set a date for the church and didn't even know anybody to marry. So it's funny to hear you say that. Well, they just wanted the concept of getting married and wanted to get married. So I think for them, they probably felt safe with you because you were doing the same thing.

[Trey]

Right?

[Joel]

Yeah.

[Burt]

Mary's gonna put this one squarely on you. Hey, Mary, you're on Q100.

[Caller Mary]

Hi. How are you?

[Burt]

Good. How are you?

[Caller Mary]

I'm doing pretty good, thanks. You know, I've been listening. I've been to the Burt show for years, and I thought it was really cute when Trey came on and was talking about getting married. I thought it was very sweet. And, you know, I actually love to be in a relationship, and I have been married before, and I'm looking for that right person. And. And, you know, I didn't want to email because I thought, gosh, if he wants to get married that badly, you know, it was kind of like, I bet the people that are going to contact him are the ones that are so desperate to get married. I mean, they're not anybody you would really want to be in a relationship with anyway. So that kind of turned me off, and, you know, I thought, why waste my time?

[Burt]

So what are you saying? It was just a. It's a desperate concept, and only desperate people would participate in it.

[Caller Mary]

I wouldn't say it's necessarily a desperate concept or desperate people would only participate in it. I just. I just felt like, well, if he's really set on getting married, then he's so much more likely to make the wrong decision in the first place. And why would I want to be involved in somebody who was. Who was, you know, possibly going to be somebody who would make a bad decision and include me in it, and then maybe I would get clouded, and, you know, I think everybody's made bad decisions, and I'm at the point in my life where I just don't want to make a bad decision or wrong choice again. Therefore, I try not to get too involved in relationships that, you know, have preconceived notions of the way things should be.

[Unidentified Male Commentator]

What are you doing on January 17?

[Burt]

What are you getting out of that, Trey?

[Trey]

It's. It's interesting. She said that I agree with her that half the people that contacted me were desperate, you know, or not desperate, but really wanted to be married. But the other half were competitive. I found, you know, they literally. The girls were like, I have to win this thing regardless of what. What it is. It's like the Bachelor. And people were telling me they're like, girls are competitive, and they'll. You know, they'll do this just to compete with other girls. And I didn't believe it, but it did show a little bit.

[Unidentified Male Commentator]

Is there anyone. Any girl who cried around you within seven days of meeting you?

[Trey]

I don't think we had any criers. We had a couple of clingers.

[Burt]

Okay.

[Joel]

Had some clingers and some stalkers.

[Unidentified Male Commentator]

I had a stage five clinger.

[Trey]

We had some clingers, which were awesome,

[Burt]

but not gonna happen. So bottom line here is, if you were a betting man and you were going to Vegas, you wouldn't bet that you're getting married. It's not gonna happen.

[Trey]

I wouldn't bet. Well, I don't know about getting married. I wouldn't bet that I'm getting married to somebody I love. I might still get married just to get married because I said I was going to get married.

[Unidentified Female Commentator]

So don't do that.

[Joel]

I wouldn't care. He'll do it.

[Unidentified Female Commentator]

We just talked about statistics on marriages that don't work. Anything. You know what? Don't get married.

[Burt]

Some women are going. That's a man of his word right there.

[Trey]

Thank you.

[Burt]

He's going to get married because he said he was going to.

[Wendy]

No, you're just going to get it annulled.

[Trey]

No, I mean, I might get married because I said I was going to get married on the 17th. One, follow through. And two, I'll have a divorce, which will make me better than not having a divorce and a great story, and it might work.

[Burt]

So of the potential women listening right now, they already know that. Yeah. You're gonna marry them just because you said you would.

[Trey]

Oh, no, no. It's love.

[Joel]

Mm.

[Trey]

About love, Joel.

[Burt]

Those two women, or whatever it is that you're. That are still in the running, are thinking, you know, what if I could just get them to marry me, I know I can change them. I know I can make this work.

[Trey]

Just give it a chance.

[Joel]

Just give it a chance.

[Trey]

Give it a chance. Just give it a chance.

[Burt]

All right, so there's your update. You guys have been emailing now for a couple of weeks. It is what it is right now. It doesn't look like there's anybody that he's very excited about marrying, but the marriage still may be on just because he told everybody he would do it. That's it. That's it.

[Unidentified Male Commentator]

Seems like there's something else. There's something else.

[Trey]

No, that's it. It's just kind of laying there. It's just it. The first show.

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[Simply Business Announcer]

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[Simply Business Female Announcer]

When you run a business, there are a lot of boxes to check.

[Simply Business Announcer]

Let's see. Payroll. Check inventory. Check insurance.

[Simply Business Female Announcer]

Well, good things. Simply Business makes getting small business insurance fast and easy. Just answer a few questions, review your quotes, and get covered in under 10 minutes, all online. It's that simple. Check insurance. Off your [e-mail].