Vault: He Needs Help Searching for His High School Sweetheart

Summary

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The Bert Show – Episode Summary

Vault: He Needs Help Searching for His High School Sweetheart

Date: March 18, 2026
Cast: Bert Show team (host and various co-hosts), Craig (guest), Blue Dog Investigations (guest investigator)

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Episode Overview

In this emotionally-charged episode, the Bert Show follows up on the story of Craig, a longtime listener and musician who has spent 17 years searching for his high school sweetheart after making "the dumbest mistake" of his life. The show’s hosts and listeners become invested as Craig expresses regret and a longing for closure (or possible rekindled romance). To help Craig, the Bert Show team collaborates with Blue Dog Investigations, who, after some sleuthing, manages to track down the elusive ex-girlfriend—and she agrees to come on-air the following day.

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Key Discussion Points & Insights

1. Setting the Scene: Craig's Story

• Craig’s Initial Call-back (01:02 – 01:32):
  • Craig, now 34, recounts his intense, long-lasting feelings for his high school sweetheart for over 17 years.
  • Quote: “I'm 34 now. I don't think day has gone by where I haven't think about her. I'm still in love.” (Craig, 01:10)
• He recalls playing the song “More Than Words” by Extreme with his band—every time he hears it, he’s transported back.
• He broke up with her at age 17, calling it the “dumbest thing I ever did” (01:32).

2. The Search

• Craig's Attempts to Reconnect (01:56 – 02:13):
  • He sought her out numerous times over social media but couldn’t locate her.
  • The Bert Show passes his information to Blue Dog Investigations to help with the search.
• Discovery & Announcement (02:13 – 02:22):
  • The show's investigator delivers the news: “Craig, I'm here to tell you that we found her.” (Host, 02:13)
  • She’s willing to come onto the show the following day.

3. Anticipation & Emotions

• Nerves and What’s Next (02:27 – 03:45):
  • Craig is both nervous and hopeful when asked what he wants: “Available and maybe willing to, you know, meet or go out... see where she's at.” (Craig, 02:45)
  • The hosts and investigator explain that the ex-girlfriend knows who is searching for her (unlike their usual “one that got away” format), but she doesn’t know the depth of Craig's feelings.

4. Revealing Intentions and Regrets

• Ten Questions and the Message (04:13 – 05:19):
  • Craig prepares ten questions he wants answered—a clue that his feelings are more than platonic.
  • He admits he sent a heartfelt message to pass along: “I just wanted her to know that I wasn't that same person that, you know, when we broke up.” (Craig, 04:59)
• The Breakup & Confession (05:28 – 07:50):
  • Clarifies his ex broke up with him, though he was to blame.
  • The co-hosts press Craig for details on the breakup:
    • He sheepishly admits: “I kissed another girl... it was actually my best friend's sister.” (Craig, 06:55 & 07:10)
    • He recognizes the impact, acknowledging it was “devastating” since he was her first long-term boyfriend (07:23).

5. Humor, Humanity, and Relatability

• Aging and Social Media (07:50 – 08:28):
  • The crew jokes about how people look compared to high school memories.
  • Light-hearted banter about sharing current photos—“I'd say clothed.” (Host, 08:10)

6. Wrapping Up and Setting Tomorrow’s Stage

• Looking for Closure or Rekindling (08:35 – 09:01):
  • They confirm the on-air reunion will take place the next morning, planning to ask Craig’s ten questions live.
  • Hosts emphasize that regardless of the outcome, Craig will get some “closure. Maybe have some peace with it and be able to either bring her back into your life or let her go.” (Co-host 2, 08:52)

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Notable Quotes & Memorable Moments

• “I'm 34 now. I don't think day has gone by where I haven't think about her. I'm still in love.”
  – Craig, 01:10

• “Dumbest thing I ever did.”
  – Craig, 01:35

• “Craig, I'm here to tell you that we found her.”
  – Host, 02:13

• “Available and maybe willing to, you know, meet or go out. Just see, you know, see where she's at.”
  – Craig, 02:45

• “I just wanted her to know that I wasn't that same person that...when we broke up.”
  – Craig, 04:59

• “I kissed another girl. And that was about it. But at the time it was really...it was devastating. And it was actually my best friend's sister.”
  – Craig, 06:55 & 07:10

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Important Timestamps

• [01:02] – Craig’s Re-introduction and summary of his search
• [02:13] – Announcement that Craig's ex-girlfriend has been found
• [03:14] – Investigator explains the situation to Craig
• [04:13] – Discussion of Craig’s 10 questions for his ex
• [05:57] – Details on the breakup and aftermath
• [07:50] – Craig explains the depth of the relationship and his regret
• [08:35] – Plans for the on-air reunion and closure
• [08:52] – Hosts reiterate the aim for closure or potential reconnection

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Tone and Language

The Bert Show maintains its trademark mix of empathy, humor, and honest curiosity. The hosts create a relatable and supportive environment for Craig, balancing teasing banter with genuine concern for his emotional journey.

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Conclusion

This episode is a heartfelt exploration of enduring love, regret, and the desire for closure. Listeners are left eagerly anticipating the upcoming on-air reunion, as Craig prepares questions for the girl he’s never forgotten. The Bert Show promises both resolution and entertainment, serving up real human drama with humor and heart.

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Transcript

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[Host (possibly Britcha)]

It's the Birch Show.

[Craig]

Previously on the Bird Show. I'm a musician. I've been in bands since I was 16. I had a high school sweetheart and we used to play Extreme all the time. My band played it with our song. Yeah, anytime that comes on, it just kills me. And we broke up when I was 17. I'm 34 now. I don't think day has gone by where I haven't think about her. I'm still in love a million times on MySpace, Facebook and all that stuff. And I can't never ever find her.

[Host (possibly Britcha)]

Alright, so that was Craig a couple of weeks ago and we sort of accidentally fell into that conversation with him. Then he sent us an email saying that, yeah, for 17 years he's been thinking about the same girl for 17 years, just in a different place in his life. And I think he ended up dumping her. Right? Yeah. And he moved on with us. Yeah. Dumbest thing I ever did.

[Co-host 1]

Yeah, I dumped her.

[Host (possibly Britcha)]

I'm a dumper. 17 years, he's been thinking about her. So we sort of latched on to the story and we gave all the information over to Blue Dog Investigations. And between them and Tracy, we've been trying to track her down because he

[Co-host 2]

had looked for her before on like MySpace and Facebook and stuff like that and just couldn't find her.

[Host (possibly Britcha)]

Craig, I'm here to tell you that we found her.

[Craig]

Yeah, I hear that.

[Host (possibly Britcha)]

And she's willing to come on with us tomorrow.

[Co-host 1]

Wow. That'll make you crap yourself, won't it?

[Co-host 2]

Are you prepared for the news? Either way, like if she's married or taken or what.

[Craig]

Yeah, I'm a big boy. I mean, I'm prepared for it either way. But, you know, I sure would like as a go in my favor now.

[Host (possibly Britcha)]

Now when you say in my favor, what would that mean?

[Craig]

Available and maybe willing to, you know, meet or go out, Just see, you know, See where? I just want to, you know, catch up and see where she's at. And if. No, it may turn into something. I don't know.

[Host (possibly Britcha)]

Now, this is going to be a little different than how we normally do the one that got away. Because normally the person that we call and find doesn't know who has been looking for them.

[Investigator (Blue Dog Investigations)]

Right. But she was a little bit skeptical, so I did tell her exactly who was looking for her. She did ask me what to expect when she comes on the air tomorrow, and I didn't exactly tell her the whole truth. She does know. She wanted to hear Craig on the air, so I sent her. The very first time we talked to Craig, which was when he was talking about the song that he couldn't listen to. So she kind of has a general idea, but I don't think she knows that you still might want a chance with her.

[Craig]

Right.

[Co-host 2]

She probably assumes that, though. Wouldn't you? Like, if you got this phone call from a radio station, you know what I'm saying, and there was some guy looking for you, wouldn't you sort of automatically think there was a romantic interest involved?

[Investigator (Blue Dog Investigations)]

Maybe. Except I just told her we just kind of want to know what she's up to.

[Co-host 2]

Gotcha.

[Host (possibly Britcha)]

Especially.

[Investigator (Blue Dog Investigations)]

Whoops.

[Co-host 1]

Especially with the basis of this relationship being extreme more than words like, why

[Host (possibly Britcha)]

would you do that, Dylan?

[Co-host 1]

What?

[Host (possibly Britcha)]

Dagger in the heart. Now, you did give us the 10 questions that you really would like answered from her tomorrow, right?

[Craig]

I did, yeah.

[Investigator (Blue Dog Investigations)]

And I did tell her that you would have a list of 10 questions. I didn't exactly tell her what type of 10 questions.

[Host (possibly Britcha)]

Now, are these gonna.

[Co-host 1]

Will this be weird?

[Host (possibly Britcha)]

Comfortable for him to ask her the 10 or for us to ask the 10? Um, I don't know, because didn't I see, like, one? Do you have any regrets in your life? Which would seem odd coming from him.

[Investigator (Blue Dog Investigations)]

I mean, I think. I think based on the list of 10 questions, that it's pretty obvious that he still has feelings for her. So, I mean, because usually when we do this, they're kind of generic enough questions to where it could be anybody from your past looking for you. And in Craig's initial email, didn't you even send Me? Like a whole message you wanted passed on to her?

[Craig]

Yes, I did. I mean, I just, you know, I just wanted to, you know, wanted her to know that, you know, even though I just wanted her to know that I wasn't that same person that, you know, when we broke up. And so.

[Host (possibly Britcha)]

Well, let's do this. Let's go into it tomorrow with the 10 questions and then I think you could sort of improvise your way around those and tell her the things you want to tell her.

[Craig]

Right. And just to correct, she did break up with me, but it was my fault. The breakup was my fault.

[Host (possibly Britcha)]

Okay, and you were how old at the time?

[Craig]

I was 17.

[Host (possibly Britcha)]

17. So, I mean, you do a lot of stupid things at 17 years old.

[Craig]

Yeah, really stupid.

[Co-host 1]

Are you gonna work on a, like a poem or something? Or, like, are you gonna have anything prepared to chair with her tomorrow? Are you just gonna try to wing it?

[Craig]

I'm just gonna wing it. Just going to wing it.

[Host (possibly Britcha)]

I'm curious about the breakup part of the whole thing. Did you end up, like, messing around on her with one of her 17 year old friends?

[Co-host 1]

Well, that's an affirmative.

[Investigator (Blue Dog Investigations)]

Yes.

[Craig]

Yeah, I did something stupid. I did something stupid.

[Host (possibly Britcha)]

Screwed around with one of her friends.

[Craig]

Well, not necessarily one of her friends.

[Co-host 2]

Sister.

[Co-host 1]

Sister.

[Craig]

No, no, no.

[Host (possibly Britcha)]

Oh, I thought you had some insight.

[Investigator (Blue Dog Investigations)]

Oh, no, I was like, just trying to guess.

[Craig]

Mom. Oh, God, no.

[Host (possibly Britcha)]

Brother, Cousin? I mean, obviously it was something so bad that you're thinking that even 17 years later she might still hold a grudge.

[Craig]

I don't know. I mean, I'm. I think may. I don't know, maybe I'm making a bigger deal of about it than she is, but. Than she would. I don't know.

[Host (possibly Britcha)]

Well, let us.

[Co-host 1]

Can you tell us today?

[Host (possibly Britcha)]

Yeah, let us be the judge of that. What is it?

[Craig]

I. I kissed another girl. And that was about it. But at the time it was really, it was devastating. And it was actually my best friend's sister.

[Host (possibly Britcha)]

Your best friend's sister? You kissed her? She's not gonna think that.

[Craig]

Did you.

[Host (possibly Britcha)]

17.

[Co-host 1]

Did you confess? Did you confess to your girlfriend or did she find out somehow?

[Craig]

She found out somehow. Oh, boy.

[Host (possibly Britcha)]

Oh, yeah. You never forget the first time you

[Craig]

got cheated on, you know, and, and it was, it was particularly bad because I, you know, I was really her first boyfriend. I mean, she had, she had a. She was actually dating a friend of mine and they dated for a few weeks and broke up. But, you know, it was just, it wasn't, you know, I was her first long Term, you know, boyfriend.

[Host (possibly Britcha)]

What is defined as long term at 17 years old?

[Craig]

I think we dated for probably a year and a half.

[Host (possibly Britcha)]

Okay.

[Co-host 2]

That is pretty long term for being that young in high school. And then do you have a current picture of yourself that you'd be willing to send to her?

[Craig]

Sure.

[Co-host 2]

Because if anybody from my high school years reached out to me, I would want to know how they aged.

[Host (possibly Britcha)]

Yeah, I'd say clothed.

[Craig]

Uh huh.

[Host (possibly Britcha)]

Definitely.

[Investigator (Blue Dog Investigations)]

You know what I'm saying?

[Craig]

Yes.

[Co-host 2]

Like in my mind, I don't know. In my mind you've probably put on 30 pounds and.

[Host (possibly Britcha)]

And you're bald.

[Co-host 2]

You might not have hair.

[Co-host 1]

Yeah, that's what Facebook is for.

[Craig]

I don't think I changed that much actually.

[Co-host 2]

Okay.

[Host (possibly Britcha)]

Yeah, none of us do.

[Co-host 2]

Which is. Yeah, yeah.

[Co-host 1]

Just for the record, I don't think I've changed that much either until I try to put on my graduation gown.

[Host (possibly Britcha)]

All right, Craig, so tomorrow morning, right around this time, about 8:45, we will get her on. We'll have the 10 questions that you want answered and then we'll improvise our way around those also and we'll find out what happens tomorrow.

[Craig]

Okay? I appreciate it, Britcha.

[Co-host 2]

Sure.

[Host (possibly Britcha)]

But one way or another, you'll know. I mean, what's going on in her life. And if there's a shot there. Some closure.

[Co-host 2]

Yeah, some closure. Maybe have some peace with it and be able to either bring her back into your life or let her go.

[Craig]

Right. If not, I'll just have to fight stiffly for Jen.

[Host (possibly Britcha)]

There you go. It's the Vert show.

[Howie Mandel]

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