Vault: She Thinks Online Dating Is Pathetic…So Why Does She Keep Doing It?

Summary

The Bert Show – Vault: She Thinks Online Dating Is Pathetic…So Why Does She Keep Doing It?

Episode Date: March 19, 2026

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Episode Overview

This episode delves into the skepticism and resistance towards online dating through the eyes of Shawn, The Bert Show’s phone screener. Despite strongly believing that online dating is for "desperate people" and swearing it off, Shawn is challenged by the hosts to give it a fair shot. The panel breaks down her latest experiences with various online dates, explores her biases, and humorously unpacks the stigma that still lingers around meeting people on the internet.

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Key Discussion Points & Insights

1. Shawn’s Initial Stance on Online Dating

• Shawn has been adamant for weeks that online dating is "stupid" and "for desperate people," despite never trying it herself.
• The Bert Show team challenges her: “You’re making a judgment about online dating, but you’ve never actually gone on a date after meeting someone online.” – Host (00:20)

2. First Online Date Recap – A Flop

• Shawn shares her attempt at an online date a few weeks prior, which she dubs as a failure.
  • “It was boring, it was dull. And I was talking the whole time. He just sat there, was very nervous.” – Shawn (00:36)
• The hosts point out she didn't maximize the online platform's matching potential, instead picking someone at random. This prompts some group ribbing about judging by photos alone:
  • “He looks fun in his pictures. You gotta tell by pictures.” – Shawn (00:57)
  • “I guess everybody can look fun in a picture.” – Bert Show Host (01:00)

3. Redo: Shawn Follows the Rules

• For her next attempt, Shawn goes "by the book," completing her online profile and focusing on compatibility.
  • “Go online, fill out the questionnaire. Find somebody that you have something in common with. 70%, 80%, 90% commonality.” – Host (01:19)
• She connects with a guy who shares her music interests and works at a college bookstore. Their first date is at the Plaza Theater, watching "The Blues Brothers."
  • “We had a lot of the same interest in music... It was a different sort of approach.” – Shawn (01:34, 03:17)

4. The Date Experience – Pros and Cons

• The group debates the value of a movie date as a first meeting:
  • “Isn't that kind of a cop out?... Movie dates in general as a first date is a bad idea. Sounds very eighth grade to me.” – Host (03:25, 03:33)
  • “It's kind of creative... When you're total strangers, it's nice to have that buffer." – Co-host (03:42)
  • Shawn appreciates the creative angle, though she notes limited conversation time.
  • She finds the guy more attractive in pictures than in real life:
    • “His hair just had this thing going on... He was average looking.” – Shawn (04:16)
• She senses more of a friendship vibe but isn’t ruling out another date.

5. Reluctance and Stigma

• Despite a better experience, Shawn’s skepticism lingers:
  • “It might be more of a friend... I could see myself hanging out with him a lot and just being friends.” – Shawn (04:34)
  • “Has it changed your mind at all about online dating?” – Host (05:10)
  • “No. And I think that may be what is still...keeping me far away because I still think it's desperate.” – Shawn (05:14)
• The hosts prod Shawn about whether social stigma is coloring her perspective:
  • “You're thinking the story that you might have to tell eventually, that you guys met on an online date, is keeping you from actually hanging out with the guy more.” – Host (05:21)

6. Group Dynamics & Running Gags

• The team suspects Shawn is holding something back, especially as she debates seeing the guy again. Their banter playfully accuses her of not being honest about her feelings:
  • “It does feel like you’re holding back, honestly.” – Host (06:08)
  • “Something’s up... it is like pulling teeth to get any info out of you.” – Host (06:22)
• Shawn insists nothing more happened, maintaining her lighthearted "always right" persona:
  • “I’m always right. I will never be wrong. It's desperate.” – Shawn (07:01)

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Notable Quotes & Memorable Moments

• On picking matches:
  “You just picked a guy randomly instead of doing what you should do when you go online... you have something in common." – Host (00:43)
• On online chemistry:
  “I could see myself hanging out with him a lot and just being friends.” – Shawn (04:34)
• On online dating stigma:
  “Your soulmate... you’re supposed to find them. Not online, not narrow searches down.” – Shawn (05:28)
• Quick-fire lighthearted moment:
  “Did you spend the night at his house?” – Host (06:19)
  “No.” – Shawn (06:21)
  “Something’s up.” – Host (06:21)

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Timeline of Key Segments

| Timestamp | Segment & Highlights | |-----------|----------------------------------------------------------------------------------------------------------| | 00:00 | Introduction and Shawn’s online dating skepticism | | 00:20 | Discussion about challenging Shawn's preconceived notions | | 00:36 | Shawn’s first unsuccessful online date | | 01:19 | Hosts propose "doing it right" with online dating (proper profiles & compatibility) | | 01:34 | Shawn describes her second date, choosing based on common interests | | 03:17 | Movie theater date discussed – hosts debate pros/cons of first date movie outings | | 04:16 | Shawn’s reaction to date’s real-life appearance | | 04:34 | Chemistry (or lack thereof) and openness to further dates | | 05:10 | Hosts probe if experience changed her perception of online dating | | 05:28 | Shawn admits stigma of "meeting online" influences her feelings | | 06:08 | Team questions whether she’s holding back details | | 06:22 | Banter about possible overnight stays; Shawn vehemently denies anything more happened | | 07:01 | Episode conclusion with Shawn doubling down on her "always right" mindset regarding online dating |

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Tone & Style

As per The Bert Show’s trademark style, the conversation blends friendly teasing, candid listener insights, and sharp wit. The group’s chemistry keeps the banter playful yet real, striking an engaging balance between skepticism and open-minded exploration of relationships in the digital age.

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In summary:
This episode humorously chronicles Shawn’s reluctance and evolving views on online dating, driven by the hosts’ good-natured peer pressure. It offers an honest look at the fears and judgments that persist, even as positive experiences begin to chip away at old prejudices—reminding listeners that even the most resistant skeptics might just end up finding something real online.

Transcript

[A]

You're on the vert show. So here she is, phone screener. Shawn has been telling us now for weeks and weeks and weeks. It's online dating thing. It's for desperate people. It doesn't work. It's stupid.

[B]

Your alternative is to have Jessica set you up with someone?

[A]

I think I'd go with match if

[C]

I were stay online.

[A]

So if you weren't listening, a couple of weeks ago, we sort of challenged Sean said, okay, look, you haven't even tried the thing. You're making a judgment about online dating, but you've never actually gone on a date and after you've met somebody online. So she did a few weeks ago, and it didn't go great. And when I say great, it. It sucked.

[D]

It was boring, it was dull. And I was talking the whole time. He just sat there, was very nervous.

[A]

Part of that was your fault though.

[D]

How?

[A]

Because you just picked a guy randomly instead of doing what you should do when you go online and that is like fill out the whole questionnaire. They match you with somebody that has like, interests of you. And then you go on the date with somebody that you have something in common with. You just randomly picked one.

[D]

He looks fun in his pictures. You gotta tell by pictures.

[B]

I guess everybody can look fun in a picture.

[D]

Which at the end of the day, he didn't want to wind up taking a picture with me. So that just.

[A]

I can't put that on.

[D]

That was weird.

[A]

I'm putting that one on you.

[D]

Okay.

[C]

Did he look fun in this picture? Cuz his mouth was open.

[D]

Were you kidding me?

[C]

You're having the best time ever.

[D]

He actually did in life.

[C]

He did?

[D]

Yeah.

[C]

See, you look fun.

[A]

The little mento smile. So we said, all right, let's do this the right way. Go ahead, go online, fill out the questionnaire. Find somebody that you have something in common with. 70%, 80%, 90% commonality. So that was her homework assignment?

[D]

Yes.

[A]

And it happened this weekend?

[D]

It did. We had a lot of the same interest in music and so we would talk about that a lot. And he asked me to go out on a date with him. And we went to the Plaza theater, which I've never been to, but it was a really cool place.

[B]

I can't believe you found someone that you're compatible with. Like Bert said, who's not in jail or therapy.

[D]

Not that I know of. And so we went there and we

[A]

furlough and it just wasn't his time for his session.

[B]

Or he could be like that. What was that guy's name? Special K or whatever that weekend. Jail?

[A]

Yeah. It's a furlough type deal.

[B]

Yeah.

[D]

So why would somebody find him for me?

[B]

He only has to go in Monday through Friday or something.

[A]

How many times did you talk to him online or did you speak to him on the phone before? He said, hey, let's meet up this weekend?

[D]

He was one of the first ones to actually send me a message, so probably, I guess, a week and a half, as long as I had the profile. We just went back and forth. He sent me, like, a whole page, and I would respond a paragraph because I didn't want to give away too much. Gonna leave a little mystery.

[A]

Sure. What was in his profile that made you think, okay, this is guy. This guy this might work out with?

[D]

It was kind of actually like mine. Just kind of random little, like, spurts of, I like this and this and that. And his music taste was really good. And so we went to see the Blues Brothers, which I've never seen, and that was just a hilarious movie. We didn't do much talking because in a movie you can't really talk. But we talked about 15 minutes before and after.

[A]

And the original Blues Brothers movie.

[D]

I guess so.

[B]

Yeah.

[A]

From back in the day.

[B]

Yeah. They're screening it.

[A]

Oh, are they? All right, so you go there, you talk to him for about 15 minutes. You go into the theater, you come out. You guys do anything after that?

[D]

No, because it was like, 10:30, and I get up early. I'm an old lady on the weekend. Oh, no, it was Thursday night.

[A]

Oh, okay.

[D]

Yes.

[A]

Okay.

[D]

And usually, typically, movie dates, you know, are pretty lame, but that was a different sort of approach to it.

[A]

Isn't that kind of a cop out? If a guy tells you he's taking you to a movie for the very first time, doesn't it seem too easy?

[D]

I think just. Yeah. Movie dates in general, as a first date is a bad idea.

[A]

Sounds very eighth grade to me.

[B]

Yeah. Not if you're going to a classic movie. Like, it's different. It's not like you're going to see

[A]

Blart, sort of a different angle.

[C]

It's kind of creative. It's a little bit different. And I think when you're total strangers, because it's basically a blind date, you know what I mean? Then it's kind of nice to have that buffer in there. You know, if it was somebody that you had met through a friend and you'd already had conversations, stuff, you knew them already, then maybe the first date would be the cop out. But it sounds like it was the right thing.

[D]

Yeah. He even mentioned that it was probably pretty lame at first, but it was a good idea. I thought, be creative. And he owned or he works at a college bookstore. That's what he does for a living. So he's pretty chill, indie looking. And he looked different from the pictures.

[A]

Better when you saw him?

[C]

Better.

[D]

Worse. His hair just had this thing going on, but I guess worse. Worse, but wasn't. You know, he was average looking.

[A]

He was better looking in his picture online than he is in person. Well, imagine that.

[C]

That's usually how I did you feel any sort of, like, chemistry with him? Like, was it.

[D]

I think it might be more of a friend. Like, I could see myself hanging out with him a lot and just being friends. Yeah, but he doesn't want to go out again this week, I think so.

[B]

There's something different about this guy because the first guy he railed on and he had no problem. And now it feels like we're pulling teeth to get information out of you. You're like, yeah, he was good looking.

[D]

Well, I don't know. I liked his style and he was cute, but I don't know.

[A]

At least you're giving him another chance, so something must have gone right.

[C]

Yeah. You're not supposed to.

[D]

I'm not closing the book. You might go out with him again.

[C]

You're not supposed to know after the first date, you know.

[D]

No, no. And we only talked about 30 minutes altogether, so.

[A]

Has it changed your mind at all about online dating?

[D]

No. And I think that. I think that may be what is still, you know, keeping me far away because I still think it's desperate. So just.

[A]

So you're thinking, like the story that you might have to tell eventually, that you guys met on an online date is keeping you from actually hanging out with the guy more.

[B]

Yeah.

[D]

Your soulmate. You're supposed to, you know, find them. Not online, not narrow searches down.

[C]

I understand her point. I don't necessarily agree, but I understand where you're coming from.

[D]

I think Jen should make a profile.

[A]

Oh, she's doing fine. You don't got to worry about.

[C]

I'm avoiding Facebook. I'm not going on online dating.

[A]

You don't got to worry about that. Okay, well, keep us posted. Sounds like nothing really has changed your attitude. It's still the same about it.

[D]

No, but I mean, there's some decent people on there, I'll give you that.

[C]

Okay.

[D]

Are you exchanging emails with other people? I haven't checked it since I went out with him. So you might be thinking I'm avoiding it because I found the one.

[A]

It does feel like you're holding back, honestly.

[B]

Yeah, you totally are. Something's going on.

[A]

Nothing.

[D]

No, no, no.

[A]

Did you spend the night at your house?

[D]

Maybe. Did I spend the night at his.

[A]

Did you spend the night at his house?

[D]

No.

[A]

Something's up.

[D]

I didn't.

[A]

I don't know. It is like pulling teeth to get any info out of you. Something's up.

[D]

Well, I mean, there wasn't much to. I guess there's not much of a story to it. Just because we didn't spend too much time.

[B]

You know, here's. Here's what it is. It's. She's starting to be proven wrong. So she's, you know, a little thrown by the fact that she came so strongly and said. She came so strong and said, I will die my dating. I'll never find anyone. Then she goes out with this dude who's actually kind of cute and fun. He likes music and took her to a quirky movie and probably talk about ways to hide a body and other stuff, that it is wrong. So she's like, you're getting close to

[A]

having to labor yourself. Desperate. If you continue to go out with this guy.

[D]

I'm always right. I will never be wrong. It's desperate.

[A]

Well, there's one right there. You're wrong right there. You're on the Birch Show.