Vault: He Hooked Up With Four Women In The Wedding Party...Now What?

Summary

The Bert Show – Episode Summary

Episode Title: Vault: He Hooked Up With Four Women In The Wedding Party...Now What?

Release Date: December 12, 2025

Cast: Bert, Kristin, Abby, Cassie, Tommy, Jamie, Crash, Knox, Callers, "Ryan"

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Main Theme & Purpose

This episode focuses on outrageous dating drama as the segment delves into a sticky situation: "Ryan," a friend of the show, is headed to a wedding where he’s previously hooked up with four of the women who’ll be in attendance – and none of the women know about each other. The hosts debate how Ryan should handle the weekend, riff on the friction and tension likely to arise, and invite listeners to weigh in with their advice, banter, and first-hand stories.

Tone: Playful, cheeky, and full of good-natured ribbing.

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Key Discussion Points & Insights

1. Setting the Scene: Ryan’s Predicament

• [01:37] The hosts introduce Ryan's situation:
  • Ryan is attending a wedding (not clear if he’s in or just attending) where four women he’s hooked up with—none knowing about the others—will also be guests.
  • He maintains cordial, possibly flirtatious relationships with all of them—“the door is always open.”
• The dilemma: Should Ryan bring a date to avoid drama, or go stag and risk things blowing up?

Key Quote

“Should he bring a date and make them all jealous? Should he go stag and fend them all off all weekend, have it be a big competition?”
— Co-host (Jamie), [01:55]

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2. Listener and Co-host Reactions

• [02:43] Caller Tammy raises skepticism about Ryan’s perceived chances, but Jamie insists:

“I know these four women. He can.”
— Jamie, [02:52]

• The "wedding hookup" myth is debated. The hosts joke about the atmosphere leading to more romantic encounters.
• Another caller, Mike, amps up the expectations for Ryan:

“This guy needs to hook up with at least two of them. And Crash could back me up on this. One of them should be outside of those four.”
— Mike (Caller), [03:31]

• The team notes reality—some of the women might have dates of their own.

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3. Ryan Joins the Conversation

• [04:31] Ryan himself calls in, sounding bemused.
  • He jokes about bailing with a fake illness.
  • Shares the breakdown: “Two [relationships] long term, two hookups.” ([05:11])
    • Clarifies “long term”—several months for two, a couple days for the others.
  • Ryan’s main concern isn’t about adding notches, but managing the drama:

“I just don’t want anybody…I’d rather bring a date and just keep everybody else at bay because…I don’t want anybody to get their feelings hurt.”
— Ryan, [05:50]

• The hosts tease his “sensitive” side.

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4. Predictions and Catastrophe Scenarios

• [06:21] Host:

“So the goal this weekend really is okay, yeah, hook up. But B, make sure that, no, there’s no bad feelings between all the women.”
— Host, [06:21]

• Ryan: “I don’t think I’m coming out of this weekend one way or the other without at least the three…finding out about each other. I just don’t want it to be a big deal.” [07:23]
• Callers warn that bringing a date might cause the women to compare notes and “the fur [will be] flying.”
• Crash (co-host) lays out a challenge:

“I would like you to come back from this wedding hooking up with one of the four, the maid of honor, and the bride and the groom.”
— Crash, [07:43]

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5. Unexpected Female Callers Throw Themselves In

• [08:02] Lisa, a caller, offers to be Ryan’s date:

“I’m available for a date if you need one.”
— Lisa (Caller), [08:02]

• Another caller, Trina, also puts herself up as a tall single woman ready for the role ([08:46]):

“So if you like tall women, let me know.”

• The hosts marvel at women’s willingness to jump into the drama and joke about “Ryan’s” appeal.

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6. A Real-Life Parallel & Gender Dynamics

• Amy (Caller) recounts being at a wedding with her husband and all four of his former hookups—leading to awkwardness and territorial feelings. Her strategy:

“So I just sat in his lap…are they sitting there thinking, ‘I’ve had your man’ or what?”
— Amy (Caller), [11:09]

• The hosts riff on the social dynamics, blaming “mothers raising us to be good boys” yet girls want the “bad boy.”
• Ryan defends himself as “a good, respectful person—just to four different women.” [09:28]

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7. Final Strategies and Movie Analogies

• Wedding is a few months away—gives Ryan time to plan.

“If I bring the same girl to that one that I bring to this one, I can probably circumvent some of the drama.”
— Ryan, [09:46]

• The hosts compare the whole scenario to a high school movie or a Hollywood rom-com (“Four Weddings and a Funeral” style).

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Memorable Quotes & Notable Moments

• “Crash could back me up on this. One of them should be outside of those four.”— Mike (Caller), [03:34]
• “I’m just worried about getting slapped or punched or a drink thrown in my face or something along those lines.”— Ryan, [05:50]
• “If this dude takes a date, we all know how catty women are. They’re gonna get talking amongst each other and then there’s gonna be fur flying.”— Stephanie (Caller), [06:49]
• “I don’t think I’m coming out of this weekend clean anyway… I just don’t want it to be a big deal.”— Ryan, [07:23]
• “I’m available for a date if you need one.”— Lisa (Caller), [08:02]
• “Are they sitting there thinking, ‘I’ve had your man’ or what?”— Amy (Caller), [11:17]
• “I’m a good, respectful person. I just happened to have run into a weekend where I was a good, respectful person to four different women.”— Ryan, [09:28]

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Important Timestamps

• [01:37] – Main scenario introduced
• [02:43] – Listener call-in: skepticism and incredulity
• [03:31] – Listener “Mike” raises the stakes for Ryan
• [04:31] – Ryan joins the show
• [05:11] – Relationship breakdown: “two long term, two hookups”
• [05:50] – Ryan’s real fear: drama, not sex
• [06:49] – Female caller warns about female dynamics at weddings
• [07:23] – Ryan predicts the doom
• [08:02] – Lisa volunteers as a date for Ryan
• [11:09] – Amy shares a parallel experience
• [09:46] – Ryan proposes a strategic repeat date

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Conclusion & Flow

The episode weaves between playful roasting, dating advice, and wild listener stories, providing both entertainment and an odd sense of camaraderie. The cast and callers dig into the comedic potential of Ryan’s challenges, explore social stereotypes, and affirm that wedding weekends are fertile ground for drama.

Above all, the episode remains fun, irreverent, and listener-focused—a relatable “what would you do?” scenario played for maximum laughs and lighthearted self-reflection.

Transcript

[Knox]

Hi, this is Knox from the podcast with Knox and Jamie. What are you reaching for? If you're a smoker or a vaper, you're reaching for nicotine satisfaction and all the problems that come with smoking or vaping. But you could be reaching for Zyn nicotine pouches. Let's talk about what Zyn helps you reach for first. It helps with variety. 10 flavored and unflavored Zen varieties in either 3 milligram or 6 milligram strengths. And also because Zyn is smoke free, you don't have to think about lingering smells or clunky devices. Whatever you're reaching for, reach for it with America's number one nicotine pouch brand. Find your [e-mail] that's zyn.com warning. This product contains nicotine. Nicotine is an addictive chemical.

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[Host (Bird Show)]

The Birch show give us a 60 second version of what Ryan is going through this okay.

[Co-host (Jamie or sidekick)]

Well, Ryan is about to be in a wedding coming up in the next couple of months and he's in it.

[Host (Bird Show)]

Or he's just attending. I'm too much information.

[Co-host (Jamie or sidekick)]

Yeah, maybe I shouldn't. Technicalities, details.

[Co-host or caller (Crash)]

He will be there.

[Co-host (Jamie or sidekick)]

He'll be at a wedding coming up in the next couple of months where he has hooked up with or hooked up with four of the women attending the wedding. Now, this is also my friend who is the type to keep really great friendship ties with all of these women. And always the door. The door is always open for those romantic encounters to happen again. So these are four women that don't know about each other, all attending the same wedding. And really, the debate that we were having was, should he bring a date and make them all jealous? Should he go stag and fend them all off all weekend, have it be a big competition? I mean, how does he handle this, this whole situation? Because most of them don't know about each other.

[Host (Bird Show)]

All right, we're gonna talk to quote, unquote, Ryan in a couple of seconds. Hey, Tammy, you're on all the hits Q100.

[Caller or listener]

Hey, guys. Good morning. Love the show.

[Host (Bird Show)]

Thank you.

[Caller or listener]

I am a little concerned that he is so sure he's gonna be able to hook up with them.

[Co-host (Jamie or sidekick)]

I'm telling you, though, I know these four women. He can.

[Host (Bird Show)]

All four.

[Caller or listener]

Yeah, but, I mean, it's been some time, and don't you think that maybe one of them has come to their senses or met somebody else?

[Co-host (Jamie or sidekick)]

No, no, he's got. They all would. Yeah, they all would.

[Host (Bird Show)]

And plus, it's a wedding. And is it true? Because the myth in guy world is that at a wedding, women are more apt to hook up because you're all feeling romantic and stuff like that, and.

[Co-host (Jamie or sidekick)]

They'Ve been drinking all day.

[Host (Bird Show)]

Okay, that's a great combination.

[Co-host or caller (Crash)]

If you're a white woman more than get out of those bridesmaid dresses. And if it's gonna take, quote, Ryan.

[Host (Bird Show)]

To do that, then, hey, Mike, you're on all the hits Q100.

[Ryan]

Hey, guys. How you doing?

[Host (Bird Show)]

Good. How are you, man?

[Knox]

Wonderful.

[Ryan]

This guy needs to hook up with at least two of them.

[Co-host (Jamie or sidekick)]

At least two.

[Ryan]

And Crash could back me up on this. One of them should be outside of those four. He's got to have some game.

[Host (Bird Show)]

What do you mean? One should be outside of the four, and one should be in the four for it to be a successful day.

[Ryan]

Exactly.

[Knox]

Come on.

[Co-host (Jamie or sidekick)]

I like Mike. I like the way you're thinking.

[Host (Bird Show)]

You're in a league that's so far away from me.

[Co-host or caller (Crash)]

Hey, Mike, how long you been married and fantasizing?

[Ryan]

Not at all.

[Host (Bird Show)]

Yeah, that would be setting the. That's setting the bar pretty high. Really high.

[Co-host (Jamie or sidekick)]

I don't know.

[Host (Bird Show)]

I think I keep it in the family.

[Co-host (Jamie or sidekick)]

This quote, unquote, Ryan might be able.

[Co-host or caller (Crash)]

To pull it off.

[Host (Bird Show)]

Hey, Brett.

[Ryan]

Yes, sir.

[Host (Bird Show)]

What's up?

[Ryan]

Man, I think it's kind of crazy you guys are assuming these other girls aren't gonna bring a date.

[Host (Bird Show)]

Jim, you would know better than I would. Are they gonna bring a date?

[Co-host (Jamie or sidekick)]

One of them might bring a date. One of them.

[Host (Bird Show)]

Okay, maybe.

[Co-host (Jamie or sidekick)]

Maybe.

[Host (Bird Show)]

And do you think this. That Ryan could work around that?

[Co-host (Jamie or sidekick)]

Probably.

[Host (Bird Show)]

Get out of here. Is that good? Hey, Ryan.

[Ryan]

Hey, guys.

[Host (Bird Show)]

How's it going, man?

[Ryan]

Oh, hanging right in there.

[Host (Bird Show)]

You have any kind of game plan set up yet?

[Ryan]

You know, I'm trying to think. Like I said, Hobby and I were talking about it last night, and the.

[Co-host or caller (Crash)]

Only plan he has right now is not to tell Hobby any more stories.

[Ryan]

Right, Exactly. I'm thinking just about coming down with an illness that weekend. I'm not going at all.

[Host (Bird Show)]

I'm trying to. If I ask questions that are going to incriminate you, then just don't answer. Answer. But I'm trying to gain a little bit more information here in the weekend. How many of these four did you have long term relationships with and how many were just like hookups?

[Ryan]

Two. Long term. Two hookups.

[Host (Bird Show)]

Two. Long term. Two hook. All right, and you're.

[Co-host or caller (Crash)]

What's long term for a person like Ryan Ryder?

[Ryan]

Three, four days.

[Host (Bird Show)]

What was the long term in the two.

[Ryan]

Several months on both of them.

[Host (Bird Show)]

All right. And the other two were just like one night stand type deals?

[Knox]

Several minutes.

[Ryan]

A couple days.

[Co-host (Jamie or sidekick)]

Okay, couple days.

[Co-host or caller (Crash)]

And yeah, he's got staying power.

[Co-host (Jamie or sidekick)]

So are you seriously considering taking a date or are you thinking about the stag situation we were going with last night?

[Ryan]

I think the issue is not that which one of the girls am I going to hook up with, because that's not really what. What I'm worried about here. I'm worried about getting slapped or punched or a drink thrown in my face or something along those lines. So I just don't want anybody. I'd rather bring a date and just keep everybody else at bay because I just. The other thing is I don't want anybody to get their feelings hurt. You know, it's not like I don't want to be there and be in a situation where you hear that, ladies.

[Co-host or caller (Crash)]

He's sensitive too.

[Host (Bird Show)]

So the goal this weekend really is okay, yeah, hook up. But B, make sure that, no, there's no bad feelings between all the women.

[Ryan]

More than anything else, it's not, you know, it's. It's. There's other people's weddings. They're close friends of mine. I don't want to be the center of attention where there's. Where there's I'm over in one corner arguing with one, and the other one's over in the other side of the room talking to somebody else about me. And that's just. That's a mess.

[Host (Bird Show)]

My God. Hold on one sec. Hey, Stephanie, you're on all the hits. Q100.

[Caller or listener]

Hey.

[Knox]

Hey.

[Caller or listener]

I'm thinking that if this dude takes a date, we all know how catty women are. They're gonna get talking amongst each other and then there's gonna be fur flying all over the place.

[Host (Bird Show)]

But it's gone this long without them all talking about it and exchanging Ryan's story. So why?

[Jamie]

Well, what she's saying is, like, one of them not knowing that the other one has hooked up with Ryan, will say, well, you see that woman that he's with? And then I can't, you know, like one will divulge the information about her to the friends now that they're all together and start talking about it. And then they're like, what do you mean? I was with Ryan. And then, you know, and then it'll, you know, snowball.

[Ryan]

I don't think I'm gonna get out of this weekend one way or the other without at least the three that I'm concerned about finding out each other. The other one, like. Like Jen was saying, we'll probably bring a date and it's kind of a non issue, but I don't think I'm. I don't think I'm coming out of this this weekend clean anyway, so I just don't want it to be a big deal.

[Co-host or caller (Crash)]

I'm extending a personal challenge to you. I would like you to come back from this wedding hooking up with one of the four, the maid of honor and the bride and the groom.

[Host (Bird Show)]

You really want to challenge yourself? Hey, Lisa, you're on all the hits Q100.

[Caller or listener]

I'm available for a date if you need one.

[Knox]

I knew it.

[Host (Bird Show)]

What is the matter with women? All right, so here you've got a guy on the phone saying, look, I'm playing four women at the same wedding.

[Co-host or caller (Crash)]

And well, she's like, there's gotta be something good about him. Four women are into him.

[Caller or listener]

Yeah, he said he's sensitive and he's got game.

[Host (Bird Show)]

All right, Lisa, hold on one sec.

[Knox]

All right?

[Caller or listener]

Uh huh.

[Host (Bird Show)]

So typical. So typical.

[Co-host (Jamie or sidekick)]

She's like, uh huh. I'll wait around for that number.

[Host (Bird Show)]

Hey, Trina. Go ahead. Trina.

[Caller or listener]

Hey, how are you?

[Host (Bird Show)]

Good.

[Caller or listener]

I was just curious if one of the women he went out with or slept with happened to be the bride.

[Host (Bird Show)]

No, no, okay, you're safe.

[Co-host or caller (Crash)]

You say no, I hear not yet.

[Caller or listener]

Well, I'm also a 29 year old single white female, so if he needs a date, I just told you, over six feet tall. Cause I'm six feet tall. So if you like tall women, let me know.

[Jamie]

Unbelievable.

[Host (Bird Show)]

How is this even possible?

[Co-host or caller (Crash)]

Listen, ladies, just so you know, ladies, the guy who, you know what, you want to call up and offer yourselves to someone. Phil Turana can't talk to a girl to save. This guy's got four of them in the same room. Leave him alone.

[Host (Bird Show)]

You know, this is our mother's fault here because our mothers raised us to be good boys. You know, be nice and be respectful. Y' all don't want that. You're not looking for that. You're looking for Ryan.

[Ryan]

I'm a good, respectful person. I just happened to have run into a weekend where I was a good, respectful person to four different women.

[Host (Bird Show)]

This wedding is going down this weekend.

[Jamie]

No, no, no.

[Co-host (Jamie or sidekick)]

It's coming up in a couple months.

[Host (Bird Show)]

Okay.

[Jamie]

All right.

[Host (Bird Show)]

So you gotta keep.

[Ryan]

So I got some time to prepare. Okay, I got some time to prepare. So I've got another one, like the weekend before or two weekends before. And I figure if I bring the same girl to that one that I bring to this one, then I can probably circumvent some of the drama.

[Co-host (Jamie or sidekick)]

I think that might be a really good idea. She's gotta be really hot. Whoever you bring, though, why are you so hot?

[Jamie]

I'm just laughing at Hobby Land, where it's like Four Weddings and a funeral, all the same, friends gathering together and going to all these weddings. And the.

[Knox]

I.

[Co-host (Jamie or sidekick)]

It's just.

[Jamie]

I. It's like it's a Hollywood film.

[Host (Bird Show)]

I don't know.

[Jamie]

It's unfolding right now.

[Host (Bird Show)]

You know what it is?

[Co-host or caller (Crash)]

It's a high school movie. Like, Jen is the lead cheerleader. Ryan here is the player stud guy. You know, which one of you guys is, you know, the high school captain? Football captain, hooked on steroids. Which one of you has this?

[Co-host (Jamie or sidekick)]

The groom.

[Host (Bird Show)]

Hey, Amy, you're on all the hits. Q100.

[Caller or listener]

Hi. I was in a similar situation, except my husband was the player. We went to a huge wedding with someone. Sorry. Sorry. We went to a huge wedding with someone that we all went to high school with. And we were at the end table at the reception, and I went to go get a drink, and I came back, and the four women that I knew for sure my husband had hooked up with in the past were sitting at the table with him. And there were no more chairs. So I thought, well, what do I do? Do I stand there? Do I talk to them? So I just sat in his lap. And then I was sitting there thinking, well, are they sitting there thinking, I've had your man or what? I didn't know how to feel about that. I didn't know if I should be embarrassed or if I should say, hey, I've got him.

[Co-host or caller (Crash)]

So what you're saying is you want to go to the wedding with Ryan.

[Host (Bird Show)]

Hey, Ryan.

[Knox]

Yeah.

[Host (Bird Show)]

Hey, Athi. Are you gonna have to tell me where to forward these emails? Cause I can already see him coming in. Man, he sounds so good.

[Jamie]

He is sensitive and he's got game and I can solve his problems for.

[Host (Bird Show)]

This poor little thing.

[Jamie]

He's all stressed out and I just want to help him out.

[Host (Bird Show)]

This is a little bit like Donald Trump getting a million dollars. The rich get richer, you know? All right, Ryan, keep us posted over the next couple months, man. I will see you later.

[Ryan]

Thanks, guys.

[Co-host (Jamie or sidekick)]

Bye.

[Host (Bird Show)]

The Bird Show.

[Knox]

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[Host (Bird Show)]

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[Ryan]

I'm not.

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