Vault: Did he ditch her for not sleeping with him?

Summary

The Bert Show – "Vault: Did he ditch her for not sleeping with him?"

Release Date: May 8, 2026

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Episode Overview

In this episode, The Bert Show revisits an ongoing listener drama involving Terry, who reconnected with a college crush and is anxious about where things stand after a recent meetup. The main focus: Did the guy Terry is interested in lose interest because she didn’t sleep with him, or is there something else at play? The show’s hosts (Bert, Kristin, Abby, Cassie, Tommy, and more) guide Terry through her predicament, offering real-time feedback—and plenty of candid banter—while dissecting modern dating dynamics and the art of “playing it cool.”

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Key Discussion Points & Insights

1. Terry's Situation Recap

• Background:
  • Terry reconnected with a guy from college.
  • She was extremely excited and worried she appeared too eager.
  • The show had previously advised her to dial down her enthusiasm and not over-contact him (01:54–02:23).
• What Happened:
  • Despite their advice, Terry texted and emailed him multiple times.
  • The guy eventually reached out via email and set up a date for the weekend (02:34–03:20).

2. The Weekend Meetup

• The Date:
  • Took place Friday night; they had dinner, drinks, and ended up making out in Terry's car (04:07–04:36).
  • He left at 10:30 pm to meet friends and did not invite Terry to his Saturday plans or the Halloween party he was attending (04:42–05:22).
• Post-Date Silence:
  • No communication from him Saturday or Sunday, leaving Terry anxious about his intentions (05:07–05:45).

3. The Hosts' Analysis

• General Consensus:
  • The hosts believe the guy was likely interested in a hookup and, when nothing further happened beyond making out, decided to move on (05:45–08:23).
  • Some speculate he was curious to see what Terry looks like now, years after college (08:23–08:32).
  • The group discusses the signs:
    • Not inviting her out again or to the party.
    • No follow-up contact.
• Memorable Quote:
  • Host: “If he was really into her, he would have invited her to the party Friday night or called her back on Saturday, but just wasn’t worth the effort.” (09:20)

4. Real-Time IM’ing & Advice

• Terry’s Next Move:
  • Against the group’s “play it cool” advice, Terry instant messages the guy live on the air (09:45–10:13).
  • She struggles with what to say, oscillating between casual greetings and wanting to show interest, despite knowing it’s likely not the best approach.
• Host Guidance:
  • The hosts repeatedly urge Terry to stop reaching out and let the guy come to her:
    • “Just play it cool. Let him come to you. Stay busy with the rest of your life or whatever. Just don’t be too overly eager.” (11:43–12:05)

5. A Caller’s (Brutally Honest) Interruption

• Listener Feedback:
  • A caller, Sue, criticizes the segment and Terry’s approach, bringing some levity and outside perspective:
    • “I just want to know why you’ve given this idiot air time. I mean, she doesn’t even know how to talk to people...like, like, like every other word, and it’s just annoying.” (10:42–10:57)
• Hosts thank Sue, with Terry taken aback but weathering the comment.

6. Final Thoughts & Takeaways

• Closure (or Lack Thereof):
  • The group agrees Terry is unlikely to get a different outcome by continuing to chase.
  • Their collective suggestion: move on or at least let the guy initiate the next contact.
  • Terry acknowledges she’s “so into” the guy and struggles to pull back, but seems to accept the advice by the episode’s end (12:05–12:44).

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Notable Quotes & Memorable Moments

• Host 1 on Terry’s persistence:
  • “You’re not taking any of our advice. You’re going to do what you want to do, and you want to instant message and call this guy, so do it.” (11:00)
• Host 4 on modern dating dynamics:
  • “He comes into town, he says to his buddies, look, I have a lead on it might be a sure thing. I’m going to go check it out. He goes and does it. It’s not working out. You guys make out, whatever. He’s not into you.” (08:01)
• Terry’s hopeful optimism:
  • “We had a great time. Like, we had a really, really fun time. Dinner was great. Like, he paid for dinner.” (06:00)
• Advice from Hosts, repeated:
  • “Just play it cool. Let him come to you. Stay busy with the rest of your life… Just don’t be too overly eager. But you’re so overly eager about this guy that he can sniff it out and then it’s a turn off.” (11:43–12:05)

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Important Timestamps

| Timestamp | Segment/Content | |-----------|-------------------------------------------------------------| | 01:54 | Hosts recap Terry’s situation, explain the context | | 03:33 | Terry joins the show, recounts the date | | 04:36 | The making out in the car - how the night unfolded | | 05:07 | Terry’s anxiety over no follow-up contact | | 08:01 | Hosts’ frank assessment of the guy’s intentions | | 09:20 | "If he was really into her..." analysis | | 09:45 | Terry IMs the guy live on-air | | 10:42 | Caller Sue's brutal feedback | | 11:43 | The hosts' “play it cool” mantra re-emphasized | | 12:44 | Show wraps up, Terry comes to terms with the advice |

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Summary & Listener Takeaway

This episode dives into the nuances of post-college crushes and adult dating, highlighting common pitfalls like over-eagerness and mixed signals. The Bert Show team delivers both tough love and empathy, reminding listeners (especially those who overthink romantic interests) of the wisdom of stepping back and letting connections develop naturally. The hosts' blend of humor, honesty, and empathy makes the segment both an entertaining and insightful listen for anyone navigating the complexities of modern dating.

Transcript

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[Host 1 (Possibly Jeff)]

Hey, the bird show. All right, so we've been dabbling in this relationship now with instant message Terry for over a week.

[Host 2]

Yeah, we've been trying to help her out because she was really into this guy that she knew in college and they had hooked up a couple times in college but never really dated. He reached out to her and she was so overly excited like she was, you know, couldn't even breathe like she didn't know how to respond. So we were trying to help her keep the mojo and not give up too much, you know, too much interest in him. Like, we wanted her to, you know, play the chase. So we helped her a couple of different times.

[Host 1 (Possibly Jeff)]

Play cool. You can't go home.

[Host 2]

And then the last time we talked to her, what was the last update? I mean, she had kind of ruined it a little bit by over. Over texting him. And then he did email her.

[Host 1 (Possibly Jeff)]

Yeah. What happened was four times she text him and emailed him over a weekend when we said, don't do anything. And she was sort of like, starting to stalk the guy, and he wasn't emailing her, calling her back. And then she did. She sent us an email. She forward us the email that he sent her about this weekend.

[Terry]

And.

[Host 1 (Possibly Jeff)]

And this was on Thursday. Check this out. You guys were wrong. Exclamation point. I didn't screw things up. Exclamation point. I think he likes me. Smiley face. I think this is gonna be a good weekend. Exclamation point. If I don't let you guys screw it up for me. Smiley face. Mm. I'm really nervous. He won't IM me in the morning. I don't think I'll be able to sleep tonight. From Terry. Okay, then I think Tracy came down here with his email and said. He said that he was coming into town this weekend and it was sort of open. Open ended.

[Host 3]

Yeah. And not just to come to town, but, like, it looked like he was gonna come to see her.

[Host 1 (Possibly Jeff)]

Whatcha munching on?

[Host 3]

I care it get healthy.

[Host 4]

Trying to help your eyes.

[Host 1 (Possibly Jeff)]

Terry is back. Hey, Terry.

[Terry]

Hi.

[Host 1 (Possibly Jeff)]

Hi. How are you?

[Terry]

I'm okay. I'm good.

[Host 1 (Possibly Jeff)]

We thought you'd be bragging today because. Because you went out on your own, you ended up emailing and texting this guy, which we would have never told you to do. We were basically saying the relationship was completely over, and here it is. You guys saw each other this weekend?

[Terry]

Yeah. No, it was really, really good. I just am like, I have a couple questions about what happened, but it was really good. It was really fun.

[Host 2]

Cool.

[Host 1 (Possibly Jeff)]

All right, so fill us in here. Friday he comes into town. Or is it Saturday?

[Terry]

He came into town on Friday and he said he was going to a Halloween party with friends. So, like, Saturday night. So he asked me to meet with him up on Friday night.

[Host 3]

Okay.

[Terry]

So we went out on Friday night, and we went to dinner and we had a couple drinks, and he walked back to my car, and then we sat in there for A while. And then we, like, made out. Oh, yeah. And then.

[Host 2]

Okay.

[Terry]

Okay, that's good.

[Host 4]

It is awkward to say he's a grown up, isn't it?

[Terry]

And then. Yeah, so we did that for a while until, like, 10:30. Yeah, like 10:30. And then he said that he had to meet some friends, and so he went to do that and he didn't ask. Now I haven't heard from him, so I'm just kind of waiting for an IM from him. And I'm wondering if I should just. I am him and say, like, you know, hey, or I had a good time or whatever.

[Host 1 (Possibly Jeff)]

All right, so let's put the pieces together. So you make out with this dude for a long time in his car Friday night. Did he say that, I'll call you Saturday? Or did he say, let's hook up later tonight or Saturday night or anything like that?

[Terry]

No, but I mean, he had to go to that Halloween party on Saturday night.

[Host 2]

He didn't invite you to go?

[Terry]

No. I guess he was going through his friends.

[Host 1 (Possibly Jeff)]

Okay. And then Saturday night, nothing. Sunday, it rolls around. Not an instant message, not a text, not an email, nothing?

[Terry]

No. I was kind of hoping that, you know, he probably had to, like, drive back, you know, on Sunday and give

[Host 2]

him plenty of time in the car to make a phone call.

[Terry]

Right.

[Host 1 (Possibly Jeff)]

So basically, buzz kill. So if we're running this through the guy filter, Friday night, he hooked up with you, hoping, you know, for something a little bit more than what you guys did. It didn't happen on Friday night and he didn't call you Saturday or Sunday?

[Terry]

No, I mean, we had a great time. Like, we had a really, really fun time. Dinner was great. Like, he. He paid for dinner. Yeah.

[Host 3]

Let's talk about Friday night, because I'm curious how you got to the point where you made out in the car.

[Terry]

We were just sort of sitting in the car for a while. Like, he was like, oh, walking back to your car. And like, we just, like, sat in my car for a while because he was like, you know, like, oh, it's like, you know, a little chilly. Let's, like, sit in the car. And I was like, okay. And then we sat in the car and then, like, we're just kind of like, talking about, like, you know, whatever. And then he kissed me. And then we made out for a while.

[Host 4]

Okay, so that's cool.

[Host 3]

Yeah.

[Host 1 (Possibly Jeff)]

But now there's.

[Terry]

I mean, I really. Thing is, like, I, like, it was like, for me, like, it was like, you know, like, spark, spine. Like, I like, you know, I'M like, obsessed. So become this person. Yeah. Like, you know, like, you know, everything, like, I've ever wanted coming through. And I just. I don't know, I'm just worried that maybe he end that night.

[Host 3]

How did it end that night? What was the last thing y' all said after you made out?

[Terry]

Well, he was just like, hey, like, so, you know, I have to go meet my friends. Like, we've had plans for, you know, I never get to see them, and I had a great time with you and, you know, I'll talk to you later.

[Host 1 (Possibly Jeff)]

Well, and you're not. You're not even capable of just letting this go. I mean, you're gonna have to email him or text him or call him and find out what happened. Right.

[Terry]

Don't you think I could, like, just name him? And I am. And be like, hey, you know, and then like, once they're talking to me, like, thank him for dinner and everything. It sounds like he was just kind of like a hookup.

[Host 4]

I think he was, buddy.

[Host 2]

Like, you're his hookup buddy.

[Host 4]

I think it was a flyby. I think you want to see that.

[Terry]

He paid for.

[Host 4]

What time did it. I mean, you gave him something, too. It was an even exchange. What time did it?

[Host 1 (Possibly Jeff)]

Not exactly. That's why he's not calling back. Yeah.

[Host 4]

What time did you get? Did he bail on Friday night to go meet his friends?

[Terry]

10:30.

[Host 4]

Yeah. So he comes into town, he says to his buddies, look, I have a lead on it might be a sure thing. I'm going to go check it out. He goes and does it. It's not working out. You guys make out, whatever. He's not into you. He bails. He's at a club with his friends by 11 o' clock Friday night, doing his thing. Halloween party on Saturday, all's cool. Back to Alabami. Done.

[Host 2]

I wonder if he was trying to just see what she looked like now.

[Host 4]

Totally.

[Host 2]

It's been a couple of years that you guys haven't seen each other, right?

[Host 1 (Possibly Jeff)]

Could have been.

[Host 4]

Are you fatter now than you were

[Terry]

when you guys see me on Facebook? And he totally made the first move. Did not.

[Host 1 (Possibly Jeff)]

If he didn't like the way she looked, it would have never progressed to the car. So my guess is.

[Host 2]

So he thought she was cute, right?

[Host 1 (Possibly Jeff)]

Yeah, I thought she was cute. And like Jeff said, I mean, he's coming into town, he's got a sure thing lined up, and the sure thing doesn't happen, so.

[Host 4]

And not only does it not happen, he doesn't want it.

[Host 3]

So does it not happen because. I mean, because they were making out? So was it. I mean, was it because he didn't want it to go any further or. He was. I mean, yeah, guys are pretty good

[Host 1 (Possibly Jeff)]

about putting the brakes on on that kind of thing.

[Host 4]

No, I think. What would have happened.

[Host 3]

I'm just saying, if they were making out in the car. How did it go from making out in the car to she's not a sure thing?

[Host 4]

He wasn't that into her. He's like, I'm gonna make out with her for a little while, but that's cool. I gotta meet my buddies by 11.

[Host 1 (Possibly Jeff)]

Or. If he was really into her, he would have invited her to the party Friday night or called her back on Saturday, but just wasn't worth the effort.

[Host 4]

I think you should. I am him.

[Terry]

Really?

[Host 4]

No, I think you should write, did you like making out with me?

[Host 2]

No.

[Host 1 (Possibly Jeff)]

What's your advice?

[Host 2]

I do feel like she deserves to get some sort of, like, closure on it. She does.

[Host 1 (Possibly Jeff)]

She's got closure.

[Host 2]

But, yeah, I think it. I think it puts you in the.

[Terry]

I actually did IM him.

[Host 1 (Possibly Jeff)]

You did? I did.

[Host 3]

When?

[Terry]

Now.

[Host 3]

Just now.

[Host 2]

What'd you say?

[Terry]

I just said hi.

[Host 2]

Is he online right now?

[Host 4]

You got to write more than that. You got to write, how are you, sunshine? How are you, sunshine? No, no, listen to me write that, because that. That. That is a. That's like a joke that you guys shared last week.

[Host 1 (Possibly Jeff)]

No, no, don't do it.

[Host 4]

Come on, do it.

[Terry]

Okay. I just wrote how are you?

[Host 1 (Possibly Jeff)]

After you wrote, hi. You wrote, how are you?

[Terry]

Yes.

[Host 4]

Did you have a good weekend?

[Terry]

I mean, not really, because I was thinking about when he was gonna call me. Oh, you mean I should write that?

[Host 4]

Yes.

[Host 2]

This is terrible.

[Terry]

I just. I just feel like maybe he just wanted to take things slow, you know, because, like, we're friends and.

[Host 1 (Possibly Jeff)]

All right, stop One second. Okay, hold on. Again. I just want to embrace you and bring you into our security net.

[Host 4]

This is beautiful. Like the seance.

[Host 1 (Possibly Jeff)]

Hey, Sue. Good morning. You're on Q100.

[Terry]

Good morning. I just want to know why you've given this idiot air time. I mean, she doesn't even know how to talk to people on how to get to talk to this guy, and now she's, like, talking like, like, like, like, like every other word, and it's just annoying.

[Host 1 (Possibly Jeff)]

Thank you.

[Terry]

Wow.

[Host 1 (Possibly Jeff)]

You're not gonna. You're not taking any of our advice. You're going to do what you want to do, and you want to instant message and call this guy, so do it.

[Terry]

Oh, Yeah, I mean, he'll like. I feel like it kind of worked last night.

[Host 1 (Possibly Jeff)]

You haven't gotten anywhere with this guy, so do what you're gonna do. We're all gonna tell you to let it go, but you're not gonna listen to us. So I'm not sure why we're even having this conversation.

[Host 4]

Has he responded yet?

[Terry]

No.

[Host 4]

Write hi again in case the.

[Host 2]

No, I don't this time.

[Host 1 (Possibly Jeff)]

Do it in capital letters.

[Host 4]

Yeah, capital high.

[Host 1 (Possibly Jeff)]

And then write, I will not be

[Host 4]

ignored in case he didn't hear you.

[Host 1 (Possibly Jeff)]

I will not be ignored.

[Host 2]

Is there somebody else on IM that you can set your sights on?

[Terry]

I mean, another crush? Like, talk to my friend or something?

[Host 2]

That might be smarter? I mean, I just think that you're going to focus far too much attention on this guy, which is what we've been telling you from the beginning. It's. Just play it cool. Let him come to you. Stay busy with the rest of your life or whatever. Just don't be too overly eager. But you're so overly eager about this guy that he can sniff it out and then it's a turn off.

[Terry]

Yeah.

[Host 1 (Possibly Jeff)]

Okay. We're gonna go. Okay.

[Terry]

Okay. But what if he IMs me back?

[Host 1 (Possibly Jeff)]

What do you do after this?

[Host 4]

If he IMs back after she gets off the phone with us?

[Host 3]

Yeah, I think we're done.

[Talkspace Sponsor Announcer]

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[Host 4]

I think you write, I really liked kissing you. I think you write that now.

[Host 1 (Possibly Jeff)]

Anyways, we've already given you advice. The advice, even if this guy instant messages you back, is to keep him chasing you. But you're not capable of doing that

[Host 3]

because we would not have told you to. I am at him in the first place.

[Host 2]

No.

[Terry]

Yeah, but it worked. I mean, I'll try to be, like, better about that. It's just, you know, like, I'm, like, sewing Dan. Okay.

[Host 4]

Okay.

[Host 1 (Possibly Jeff)]

Good luck with that. Yeah.

[Host 3]

I'm glad y' all made out.

[Host 2]

Good luck.

[Host 4]

Call us back. Keep us posted.

[Host 1 (Possibly Jeff)]

See you around The Birch Show.