Vault: She Hooked Up With His Dad Before They Even Met

Summary

The Bert Show – Episode Summary

Episode Title: Vault: She Hooked Up With His Dad Before They Even Met
Air Date: April 9, 2026
Main Cast: Bert, Kristin, Abby, Cassie, Tommy, and more
Featured Caller: “Courtney” (name changed, voice disguised)

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Episode Overview

In this episode, the Bert Show crew tackles a jaw-dropping listener dilemma: a woman, “Courtney,” believes she may have slept with her current boyfriend’s father—before she ever met her boyfriend. The segment explores Courtney’s predicament, her panic over being invited to a Father's Day party, and an animated debate among the co-hosts and callers about what she should do next.

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Key Discussion Points and Insights

Courtney's Story: The Setup

• [02:31] Courtney shares her tale from the beginning, detailing two separate relationships:
  • Two years ago: She met a man at a happy hour, dated briefly, hooked up once, and then parted ways amicably.
  • Last year: She met someone new on a dating app, started a serious relationship; he's younger but they connect well.
• The Problem: Courtney’s boyfriend invites her to a Father's Day party. When shown a photo of his dad, Courtney is struck—she realizes he is the same man she hooked up with two years ago.

  “When I first met my boyfriend, I thought he looked familiar, but, oh my God, I never really thought that. ... It is the same name.” – Courtney [05:28]

Confronting the Panic

• [05:54] Courtney is unsure if she can face the situation, reeling with anxiety over possibly running into her boyfriend’s father, and fears both men will realize the connection.
• After seeing the photo and recognizing the name, Courtney starts making excuses to her boyfriend to avoid the party.
• Hosts express disbelief at the odds:

  “What are the chances?” – Cassie [05:49]
  “I am completely freaking out.” – Courtney [05:56]

Untangling the Family Drama

• [06:28] Hosts question how the topic of the boyfriend’s father never surfaced in a year of dating.
  • Courtney explains the bad divorce, the father-son estrangement, and lack of discussion about the dad.

  “He doesn’t talk to him. ... For the past couple of years, he felt like it was his dad's fault.” – Courtney [06:41]

• Hosts emphasize eventual confrontation: the past can’t stay hidden forever.

The Ethics and Tactics Debate

• The team splits on advice:
  • Be Honest: Several (especially callers) say Courtney should tell her boyfriend right away.

    “She really needs to be honest and just tell him. She has to tell him.” – Robin, caller [14:06]

  • Conceal and Avoid: Others propose deflecting, drastic makeovers, or skipping the party altogether.

    “Is there a way, if you have to go this weekend, that you could drastically change your look...?” – Cassie [09:20]

  • Extreme Theories: Joking suggestions range from fabricating stories about the dad’s behavior to proposing a "Saturday night threesome" (met with clear disgust).

    “Everything’s lined up perfectly for a little Saturday night threesome.” – Jeff (joking, met with 'eww’s all around) [15:22]

  • Cynical Advice:

    “Just totally separate them even further already.” – Cassie, suggesting distancing the boyfriend from his dad [14:42]

Uncomfortable Humor and Notable Dialogue

• The panel’s characteristic irreverence shines, with a blend of empathy and shock. Some moments cross into raunchy or uncomfortable territory (“junk comparisons,” “multi-generational junk touching”).

  “Have you noticed, like in the course of you dating the son, do their genitals look the same?” – Jeff (met with groans) [10:35]
  “Julia Roberts movie, this.” – Bert, comparing the situation to a wild romcom [09:35]

• Some hosts and callers express sympathy and highlight the randomness and innocence of Courtney’s situation.

  “This is an honest, like, accident that has happened. ... She's done nothing wrong.” – Kristin [13:23]

Resolution? (Or Lack Thereof)

• No consensus is reached; the majority agree that, sooner or later, honesty is inevitable.

  “Eventually she has to say something. ... Do you want to do it this weekend? Do you want to do it next month? ... It’s got to be said.” – Bert [16:22]

• Courtney is unsure but leans toward going to the party for confirmation, hoping against hope it’s all a strange coincidence.

  “I’m leaning towards going just to ease my mind and pray that I’m just...” – Courtney [16:34]

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Notable Quotes & Moments with Timestamps

• [03:08] Courtney’s Bombshell:

  “I think I may have slept with my boyfriend’s father.” – Courtney

• [05:28] Realization Sinks In:

  “As I look at this picture... Oh my God, I never really thought that. ... It is the same name.” – Courtney

• [07:18] 'Multi-generational Junk Touching':

  “...you will have to interact with his father, which means you have had multi-generational junk touching you.” – Jeff

• [09:20] Makeover Strategy:

  “Is there a way... you could drastically change your look… so that it's so different from when you went on the original date?” – Cassie

• [13:23] Accident, Not Guilt:

  “This is an honest, like, accident that has happened. ... To her, she’s done nothing wrong.” – Kristin

• [16:22] The Honesty Countdown:

  “Eventually she has to say something. ... It’s got to be said. So it’s your turn.” – Bert

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Conclusion

Episode Mood: A blend of shock, humor, disbelief, and a dash of empathy. Courtney’s situation teeters between soap opera and comedy, with no clean solution in sight—only the guarantee that secrets rarely stay buried.

Takeaway:
The Bert Show turns a wild, one-in-a-million dilemma into entertaining, thought-provoking radio. They remind us that life’s messy surprises demand both laughter and hard truths—and that even the “craziest storyline” can happen to anyone.

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For the outcome, listeners are encouraged to “check back on Monday.”

Transcript

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[B]

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[A]

this is accurate and this goes down the way it's supposed to go down this weekend, this will be a shocking call to take on Monday morning.

[C]

Yeah, I'm totally intrigued to find out what it is. You said it's the Freakiest Father's Day scenario or something like that.

[A]

Yeah, I think we've had. I mean, in the course of seven years of dysfunction, we've had a lot of bizarre storylines.

[D]

Had them all.

[A]

You think? We've had them all. And this one might have been one that we've had before also, but certainly not recently.

[E]

Okay.

[D]

It's always worth revisiting the fun ones.

[A]

We're gonna call her Courtney, and she's on the voice disguiser, and she's very sensitive about times and dates and stuff like that because she doesn't want people to know that it's her. So, Courtney, rather than me ask you questions that could lead you into problem areas, why don't you just go ahead and tell us right from minute one to where you want to leave it?

[F]

Okay.

[A]

Okay. And you got to speak up for us, please.

[F]

Oh, okay. Let's see. Where do I. Okay, we'll start. I guess we'll start with the title. I. I think I may have slept with my Boyfriend's father.

[E]

Okay.

[A]

I think I may have slept with my Boyfriend's father.

[D]

Save that

[A]

setup. Okay, details.

[F]

I'll start at the beginning. About two years ago, I was at a after work happy hour, and me and a few co workers and someone sent me a drink over and I saw him and I went over to thank him and we started talking. He was a nice guy, and so we exchanged numbers, we went out a couple of dates, and we, you know, hooked up once. And then after that, he said that, you know, he wanted date around. He had just got out of a serious relationship. So I never heard from him again after that. So that was. That was that. So we'll fast forward to last year. I was online on an online dating site and someone sent me a message and I saw how old he was and I told him that I was not interested because he was too young. He was very persistent. And after a couple emails back and forth and a couple of IMs, I finally said, you know, coffee won't kill me. We can go out. So went out with him, we started dating seriously. And that was last year. And we can. We have a really good relationship. I really like him. The fact that he's younger than I am doesn't seem to matter. Okay. Earlier this week, we were having dinner at his place, and he asked me what I was doing this weekend, and I told him nothing. And he said, well, you know, there. There's going to be a party this weekend for my dad for Father's Day, you know, would you like to Go. And I said, well, yeah, sure, of course. And I said, you don't talk about your dad a lot. And he said, well, we used to be close because he had me when we were kind of young, so. But when his mom. When my mom and he got divorced, he and I weren't as close. He said, but my mom asked me to go to this party. So I said I would. And he's like, okay, did you want to see him? And I was like, of course. So he goes and he gets this picture of him with his father. And I'm not positive, but it looks just, like, unreal.

[D]

Good stuff right there.

[F]

So, I mean, as I look at this picture, I'm thinking to myself, you know, when I first met my boyfriend, I thought he looked familiar, but, oh, my God, I never really thought that. So I'm looking and I said, well, what is his name? And he tells me his name, and it is the same name.

[C]

What are the chances?

[D]

Bring it.

[F]

Okay.

[E]

What are the chances?

[F]

I am completely freaking out. And so I don't know. So I haven't seen my boy. And that's really odd that we don't see each other at least three or four times a week. So I told him that I am extremely busy at work and that I may not be able to go to the party because I have to work on this project because I don't know what to do. Like, I don't. I don't. I don't know. Like, I don't know. So this is why I'm here. I don't know.

[A]

Okay, let me ask you this.

[E]

Wow.

[A]

The only thing that doesn't make a lot of sense to me is if you're dating this guy for one year, why is the definition between the father and your boyfriend? How come that has never come up before?

[F]

Well, because he said, as the divorce was what separated him. He doesn't talk to him. He doesn't even really talk about him. Like he's. He quote, unquote, went to his mother's side, like, after. Apparently the divorce was really bad. And so even though he was close to his father in the beginning, for the past couple of years, he felt like it was his dad's fault. So he said he wouldn't even go normally to this Father's Day celebration, but his mother asked him to.

[C]

So his mother and his father have obviously resolved their differences, apparently.

[F]

I don't know. I didn't at that point. Once I saw the picture, I didn't really ask anyone.

[C]

Oh, my God.

[D]

All that stuff is Irrelevant relevant portion is that at some point, should you stay in a relationship with this gentleman, with this young man you call your lover, should the two of you remain close, you will have to interact with his father, which means you have had multi generational junk touching you.

[E]

Oh God.

[C]

Do you.

[E]

And I hate. And I'm not trying and I don't want to. This is not an insult to you, but do you think the father's going to remember you? Was it that significant of a time together? You said you just went out a couple times, right?

[F]

We only went out a couple of times and it was only at once. And I think, I don't know. And the only, like I don't think so, but I don't know. Like that was a couple of years ago and the way that he was talking about our situation, it just seemed as if I was probably the first like his first part out. After the divorce. He told me he had children.

[D]

Yep. He'll remember you.

[A]

I agree. You think he'll remember 1000% if it's a one night stand, I would say he might, he might not. But they went out a couple of different times. And generally as a general statement. Well, I'm not even gonna say that. Accurate.

[D]

I don't know if it's accurate, but the first one I was gonna say

[A]

that most guys remember the faces of every woman that they slept with.

[C]

Depending on how many they've been with.

[A]

That's gonna be the asterisk for me is depending. Like I've got friends that have had so many that they might not not know. But like a guy like me would

[C]

remember the face of whomever I said.

[G]

Steve.

[D]

There was, there was. What was I going to say in the fact that he was the first one out of the. You were the first one out of the divorce. Out of the gun. After the divorce. He'll remember you. You're significant.

[E]

Because I thought if he doesn't remember, then I wouldn't even ever bring it up.

[C]

Is there a way? I'm sorry, go ahead.

[F]

I don't want to go, but I don't know. I mean, I really, really, really, really love my boyfriend and I don't. And I don't know if I can avoid seeing. Even if I, even if I get out of this weekend, if their relationship is not close, maybe I can avoid it.

[D]

Nope, you got to deal with it.

[C]

Is there a way, if you have to go this weekend that you could drastically change your look, like your hairstyle or something so that it's so different from when you Went on the original date. He might get confused.

[F]

Maybe. I don't know if I have time. I guess I could.

[A]

Can we please stop here and let's stop the fantasy. I mean, if she is in love with this guy. I mean, you're talking about a Julia Roberts movie. This. I mean, if she's really in love with this guy, she's gonna. It's gonna have to come up.

[E]

Can't she just say she went out with her dad instead of having to go into the details of Melissa, I

[A]

think you have to be consistent in your advice, Melissa. And normally you say be honest.

[E]

Well, she's gonna sabotage her relationship. Then if she says I slept with your dad, the relationship'.

[A]

How is she going to go on with this relationship if it never comes out? What if it's going to have to be addressed eventually? It's the same dude's name and she's seen the picture.

[C]

Is it a name or is it like John or Bob or something?

[F]

It's a little more unique than John or Bob, but it's not like, you

[C]

know, it's not crazy.

[F]

Yeah, it's not crazy. It's in between.

[E]

So I feel bad for. Because she didn't ask for this.

[D]

I have a technical question.

[E]

Wow.

[C]

It's weird. I guess. You know what you like Courtney.

[A]

Melissa loves consistency. Do whatever.

[D]

Have you noticed, like in the course of you dating the sun, do their genitals look the same?

[C]

Oh, come on, jeff$disgusting.

[E]

Well, at least Jeff's consistent too.

[C]

Disgusting.

[F]

The first one. So I don't really. I wouldn't say I would. They do have similarities, though.

[A]

Oh, really?

[D]

Do they have common, like, movements or techniques or.

[C]

Stop, stop.

[A]

You said that they have some similarities.

[F]

Now you got us all physical similarities. Not in. When I saw it. When I first met my boyfriend, after we met online, I looked at him and I thought he looked familiar. And then when I saw him in the picture with his dad, that's why he looked familiar.

[A]

Oh, okay, so you're not comparing junk to junk.

[F]

No, I was not comparing.

[A]

Well, that's what it sounded like.

[D]

But you know what they say.

[C]

This is because Jeff said that sounded

[A]

like a junk comparison.

[D]

It's an interesting situation because they tell you, like, you can look at a girl's mom to see what she'll look like. Like, you know, what your boyfriend's junk's gonna look like in 30 years.

[F]

Oh, my God. Oh, my God.

[A]

Boy, did you call the wrong stage.

[E]

Well, she would like it because she slept with the dad already, so she's Gonna like what he's gonna turn into.

[D]

All right, here is, I made love to your father.

[A]

Actually, Trey here says, this is not a big deal. Trey, go ahead.

[G]

Yeah, I would just comment about that. If it's not that big of a deal, she should just go ahead and meet with the father and explain it to the boyfriend. Because if she really is serious about this guy, let's just say later on down the line, she wound up wanting to marry him. All of a sudden, she has to meet up with the father, you don't want to get married. Then all of a sudden, he finds out, and then things go sour.

[A]

So, Trey, let me. Let me hear you out here. Were you suggesting. Go to the father first and say, look, I'm in love with your son, and things look really good, so let's keep the secret ourselves.

[G]

I would say sit down with the son, explain it to the son. Because eventually, somewhere down the line, she's gonna have to face the father.

[A]

Let me go with my theory.

[E]

Let's talk about Jeff. Stacy and Jessica say, oh, my God. Guess what? I slept with your dad in the past.

[A]

Done. Relationship over. Over. Done.

[D]

I get the impression from Bert that back in the day, everybody slept with his father. So if Jessica did, so be it. He just seems to be the partying type of guy.

[A]

Let's go with the mistake that I thought he said. What if she sits down with the dad beforehand and says, look, this happened. I'm dating your son now. He never needs to know. Never needs to know about this.

[E]

I just think they're not even close,

[A]

the father and the son.

[E]

The more conversation she like, the more she does behind his back, the is going to be when he finds out. This is an honest. This is an honest, like, accident that has happened. And to her. To her, she's not. She's done nothing wrong.

[G]

Right.

[E]

But if she goes and sits down with the dad, then she will have done something wrong.

[A]

You're right, though. If you. When you post that question.

[E]

It's done.

[A]

Yeah, it's done. No way.

[G]

Ew.

[A]

Oh,

[F]

Absolutely positive.

[E]

But if Katie slept with Millie Pete, I don't think I could handle that.

[G]

Save that.

[C]

No, no.

[F]

This is funny.

[D]

Well, just so you know, if Millie Pete was interested in Katie, you wouldn't be here.

[F]

No, no.

[A]

Hey, I'll take one more call here. But everybody's calling up and, you know, saying. Using the same ridiculous advice, and that's to be honest. Hey, Robin, go ahead. You're on Q100.

[G]

Yeah, she really needs to be honest and just tell Him. She has to tell him.

[A]

Why?

[G]

She has to tell.

[A]

It's gonna come out eventually.

[G]

Gonna come out. Exactly. It's gonna come out. So she needs to just tell him.

[D]

Maybe you could rekindle the stuff and just tell the guy it's a father's day gift from his son and just have it be like a one off annual type of. Hey, what's up?

[E]

I'm so sorry.

[F]

Tell him what you did.

[E]

Nothing wrong.

[F]

You just have to go to the. And then. See, I don't want to. It's a Father's day party. I don't want to go there and go, oh, yeah, by the way, as long as you're celebrating.

[C]

No, I say keep it from him. I say keep it from him. And he, like, really trash the relationship with his dad. Like, God, he's such an awful person. You. It's good you took your mom's side and, like, totally separate them even further already.

[F]

Not close. See, I don't go to this thing this weekend because I'm busy. I have worked.

[C]

Yeah. And be like, why? Why do you want to support a man that.

[A]

Why can't you go and then make up a story afterwards and say, oh, my God, your dad inappropriately touched me. You should never talk to him ever again. And then he'll accuse his dad, the dad will get mad and then fabricate the story while I hooked up with her three years ago. And by that time, the son will never believe the story.

[D]

I think everything's lined up perfectly for a little Saturday night threesome.

[F]

Oh. Ew.

[A]

Hey, Adam is a psych major, so let's all stand back.

[C]

Okay.

[A]

All right, Adam, go ahead.

[D]

Hey, guys.

[E]

Major.

[F]

Hey. I just.

[H]

I feel really bad for your situation, for one, but, I mean, I seriously do believe that it just won't work out. I mean, based on.

[D]

Thank you.

[H]

As. I mean, I guess your lover, the son in this case is looking at, you know, you. He always sees his father as. As having, you know, like his one love. Does that make sense? I mean, I guess as far as. As far as I'm concerned, I can never do that.

[A]

No, No.

[H]

I would always see his face in the place of your face.

[A]

Oh, gross.

[C]

That's twisted. Maybe he needs a therapist.

[E]

Like you're doing your dad. What was his name?

[C]

Psychologist. Yeah.

[E]

Yeah.

[A]

I don't know where to go with this. Here.

[C]

Don't tell, don't tell, don't tell, don't go to the picnic or whatever.

[A]

I mean, eventually she has to say something. So do you want to do it this weekend? Do you want to do it next month? Do you want to do it in six months? Do you want to do it in two years? It's got to be said. So it's your turn.

[C]

Never, never, never, never.

[A]

So you say don't even go.

[C]

No.

[F]

My friend has already said that he's bringing someone. He hasn't necessarily said who because. So I don't know, I'm leaning towards going just to ease my mind and pray that I'm just.

[E]

Just to save. It's him.

[F]

Yeah, like it's somebody. Just because, like whoever.

[A]

Just to get 100% proof.

[D]

I think just. I think just. So all cards are on the table. Your boyfriend has to sleep with your mom. Then everything's all even playing.

[A]

Hey, Courtney, we'll check back with you on Monday morning, okay?

[F]

Okay.

[A]

Hey, thanks for sharing with us. We appreciate it. Happy Friday. Hey, the bird show.