Full Show PT 2: Monday, March 16 [Vault]

Summary

The Bert Show – Full Show PT 2: Monday, March 16 [Vault]

Date: March 16, 2026
Hosts: Bert (Host, possibly Birch), Wendy, Jeff, Ann, and others
Episode Theme:
This episode of The Bert Show continues its signature blend of real-life relationship drama, lively banter, and honest listener interaction. The primary focus is on navigating unexpected or awkward social and romantic situations, with lots of laughs and authentic reflections from both the cast and their listeners.

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Main Segments & Discussion Points

1. The Aftermath of the "Find a Cruise Date" Experiment

[00:45 – 15:18]

Overview

The central arc of the episode is a follow-up with Richard, who previously asked the Bert Show to help him find a companion for a five-day cruise after a breakup. Listeners were involved in selecting Christy, a near-stranger, as his travel partner.

Major Discussion Points

• Background Recap:

  • Richard had a cruise planned for himself and his (now ex-) girlfriend. After the breakup, he came to the show to help him find a cruise companion with just two days to decide.
  • Christy was picked more on a whim, not expecting to be chosen. As Jeff notes, "she entered it originally as a joke..." ([01:43])

• Initial Encounter and Cruise Experience:

  • Christy showed up at the airport, surprising Richard.
    • Richard: "She actually showed up at the airport, which was a big step." ([03:16])
  • The first day felt "awkward," but things were civil, and both tried to get comfortable.
  • They stayed in separate beds; sharing a small stateroom was awkward but manageable.
    • Richard: "It was definitely awkward hanging out that much with someone that you don't really know." ([04:49])

• Chemistry (or Lack Thereof):

  • By day two, both realized there was no romantic connection.
    • Richard: "...by the second day we realized this isn't really, you know, we're not really compatible." ([05:35])
  • They transitioned to friendship, but even that felt forced at times.

• Making the Best of It:

  • The pair befriends Bill and Ann from Ohio at a formal dinner and spends most of the cruise with them.
    • Richard: "We hung out with them most of the rest of the cruise and they made it a lot more fun." ([07:58])
  • Most notably, Ann from Ohio joins the call to share her perspective—she confirms the absence of chemistry but insists both Richard and Christy are "really, really cool people." ([12:23])

• Awkwardness and Social Dynamics:

  • As the cruise progressed, Christy and Richard grew more distant—even sitting on opposite sides of Ann and Bill at meals.
  • Christy missed one dinner entirely, signaling increased discomfort.
    • Richard: "She said she's going back to the cabin and she just didn't show up for dinner." ([13:23])

Memorable Quotes

• "Could you tell that there was zero chemistry going on there?" – Host, to Ann ([09:25])
• "I don't recommend a five day cruise as a second date, but it was fun." – Richard ([15:15])
• "I think the problem in your relationship with Christy was Ann. She's definitely into you… Bill and Ann are actually swingers." – Jeff, jokingly ([14:42])

Segment Highlights

• [04:37 – 05:16]: The hosts delve humorously into the perils of cruise room etiquette.
• [07:03 – 08:10]: Richard grades the experience a "four" out of ten; the group questions what felled the trip.
• [09:04 – 12:23]: Ann from Ohio shares outsider insight, confirming the authenticity of awkward vibes.

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2. Listener Dilemma: Hooking Up With The Boss’s Ex

[15:38 – 26:21]

Overview

The second big segment features "Jillian," a caller on voice disguiser, who seeks advice after unintentionally hooking up—twice—with her supervisor's ex-husband.

Major Discussion Points

• How It Happened:

  • Jillian details meeting and sleeping with a man after a night out. Only later does she learn he is the ex-husband of one of her (many) supervisors.
    • Jillian: "I had absolutely no idea that this is my supervisor's ex husband." ([18:26])

• Ethical and Professional Concerns:

  • The main debate: Should Jillian tell her supervisor? Is it wrong to continue seeing him?
  • She's concerned about overstepping professional boundaries or violating unwritten social codes.

• Listener and Host Advice:

  • The consensus is that if she and the supervisor rarely interact (and given the divorce was years ago), there's no immediate need for disclosure.
    • Ann (listener): "If it's been two years, I would say she's probably well over it. And if she didn't even know, there's no reason for her to be worried about it." ([22:04])

• Children & Ongoing Relationships:

  • Additional callers raise the stakes if children had been involved (they are not), as ongoing contact would make things more complicated.
    • Wendy: "If they're… If they don't have children, then they don't necessarily have a reason to be in contact." ([24:49])

• When (or If) To Disclose:

  • The consensus: If the relationship with the ex-husband becomes serious or exclusive, then disclosure would be necessary.
    • Ann (listener): "If they decide to start dating… that's the time to bring the supervisor in on it." ([25:50])

Memorable Quotes

• "Am I wrong? Can I still see him? ...I need somebody to really tell me that I can't." – Jillian ([20:53])
• "Most are calling up saying you don't owe the supervisor anything, yet you hooked up with the guy twice." – Host ([25:56])
• "Just don't screw him over, because then he may call the ex-wife and say something." – Wendy ([26:12])

Segment Highlights

• [16:12 – 17:10]: Jillian recounts the hazy initial hookup and her surprise at the next-day revelation.
• [22:37 – 23:56]: Listeners debate where responsibility lies: with Jillian or her new flame to tell the supervisor.
• [25:40 – 26:21]: Final advice and consensus is shared; the theme is caution but honesty if things get serious.

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Notable Quotes & Moments

| Timestamp | Speaker | Quote / Description | |-----------|-------------|--------------------------------------------------------------------------------------| | 01:43 | Jeff | "...she entered it originally as a joke, like a friend of hers...she was kind of like, oh, okay, it's cool." | | 05:35 | Richard | "By the second day we realized this isn't really, you know, we're not really compatible." | | 07:03 | Richard | "I'd say it's about a four." (rating his cruise experience) | | 09:48 | Ann (Ohio) | "...by the second night, we could kind of tell that it probably wasn't going to work. Just not much chemistry." | | 12:23 | Ann (Ohio) | "We had fun. I mean, they're both really, really cool people...it's just one of those things that just didn't work out." | | 13:23 | Richard | "She said she's going back to the cabin and she just didn't show up for dinner." | | 15:15 | Richard | "I don't recommend a five day cruise as a second date, but it was fun." | | 18:26 | Jillian | "I had absolutely no idea that this is my supervisor's ex husband." | | 20:53 | Jillian | "Am I wrong? Can I still see him? ...I need somebody to really tell me that I can't." | | 25:55 | Host | "…once it gets exclusive, that's the time to bring the supervisor in on it?" | | 26:16 | Host & Wendy | "Handle it delicately. But you don't owe her anything just yet." |

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Summary Table: Important Segments & Timestamps

| Segment | Timeframe | |--------------------------------------------------------------|-------------| | Richard’s Cruise Recap & Awkwardness | 00:45–15:18 | | Listener Call: Supervisor’s Ex-Husband Hookup Dilemma | 15:38–26:21 |

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Tone & Style Notes

• Conversational, humorous, and occasionally irreverent.
• The hosts keep things light even when discussions get awkward, often using self-deprecating jokes or friendly ribbing.
• Listeners’ voices are featured and respected, contributing to the community feel.

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For Listeners Who Missed the Episode: Key Takeaways

• Don’t expect romance—or even comfort—when you go on a five-day cruise with a near-stranger.
• Platonic adventure can still be valuable, even if a little awkward.
• Modern dating and workplace relationships always bring complications—transparency is key if things go from fling to serious.
• The Bert Show turns real-life messiness into lessons and laughter, unafraid to sit with the awkward or push for honesty (and a good punchline).

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Transcript

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[Host (possibly Birch)]

The Birch show the last time that we had Richard and Christy on, this is what she sounded like. He came to us and he said, look, I've got this five day cruise and it was for me and my girlfriend, but she broke up with me and, and I still want to go on the cruise and I'd like to find a girl that I'm fairly compatible with. But the problem is we only have like two days to find her. So we made that a personal challenge and we took it to you guys. And he went out and he talked to a couple of different girls and he decided that Christy was the girl that should go on the cruise with him. And this is what she sounded like the last time we had her on.

[Ann]

I'm looking forward to it. A little nervous, a little apprehensive. I had really low expectations. Like I was expecting to go and meet him for a drink and, you know, not really like him, but he was actually, you know, funny and we had a lot to talk about and. Yeah, so why not?

[Host (possibly Birch)]

Okay. At that point, she sounds pretty excited, but Wendy said by the end of the conversation, you say she sounded a little apprehensive.

[Wendy]

Yeah, she sounded a little nervous, like she didn't want to go, but she got picked so she had to go.

[Jeff]

Yeah, the way it came about was like she entered it originally as a joke, like a friend of hers. Right. Sent the first line in. And then when she actually progressed down through the vetting procedure and found out that she was process, I mean, she found out that she was really going to be one of the finalists, she was kind of like, oh, okay, it's cool. Cruise started as a joke.

[Richard]

Okay.

[Host (possibly Birch)]

So the Reality was hitting her.

[Wendy]

Well, you know, I just interpreted it as she's nervous and here she is getting picked and it's, you know, it's, it's going to be an awkward situation to begin with, even if it turns out fine. So I didn't really read too much into it.

[Host (possibly Birch)]

And I said this earlier. You know, when you travel with anybody, it doesn't matter how long you've been with them. I mean, my wife and I just went on vacation. We've been with each other for 14 years. It's tough to travel. You want to do one thing, she wants to do the other. You want to eat here, she wants to eat there. You want to chill out, she wants to go on a tour. So it's always a little bit of, you know, compromise going on. Now you add to the equation here, a cruise where your stateroom is all of about eight by eight and you're basically right on top of each other. And you've really never had anything except an hour conversation. So anything can happen at that point.

[Jeff]

Like you can't. It's not a situation where running in the water in the, running the shower in the bathroom's gonna be enough to cover up your farts. Like she's going to hear it.

[Host (possibly Birch)]

You're gonna have to tell her you're gon have to go to another deck.

[Jeff]

Right.

[Host (possibly Birch)]

So here is Richard back from his cruise. How are you?

[Richard]

Good, how are you?

[Host (possibly Birch)]

I'm okay. All we ask for you because we, we, we did do this whole thing to try to find you the right girl is just give us some brutal honesty on exactly what happened. Because from the time you left here, things look pretty good. Guys are ready to go, ready to do this five day cruise together.

[Richard]

Yeah. At first she was a little apprehensive, but she actually showed up at the airport, which was a big step.

[Host (possibly Birch)]

Were you shocked?

[Richard]

I was shocked. She pulled up and I'm like, at least have a ride to the ship. And we got on board, laid around the pool, had some drinks, had some conversation. It was a little awkward the first day. Just trying to get to know each other and you know what's going on. Who's.

[Jeff]

So you went very fast. How does it go when you get to the room? Because cruise ship beds are either two separate small beds or they've removed the dresser and they kind of push them together.

[Richard]

Well, they're two separate beds, so it wasn't an issue.

[Host (possibly Birch)]

Okay, but you were at the hotel before that for a whole night? No, no, no, no. Right to the cruise I flew that

[Richard]

morning and then she picked me up.

[Host (possibly Birch)]

Gotcha. Okay.

[Richard]

So, yeah, I mean, we spent second day basically at sea, lounging around in the sun, having frozen drinks, relaxing. Not a lot of conversations.

[Jeff]

Well, hold on a minute, hold on a minute.

[Richard]

All right.

[Host (possibly Birch)]

We're going awfully fast. Actually, I'm with Jeff on this. We're accelerating too fast, like, because you pretty much know in the first five minutes of a conversation things are going to go well. Or not.

[Jeff]

Yeah. You're yada yada in this. So you get on the boat and then everything's great. Then you have some drinks, right. And things are. So if you get good and buzzed.

[Richard]

Yeah, I'd say so. Yeah.

[Host (possibly Birch)]

Okay.

[Jeff]

All right. So then you, then it. Then you know, fast forward. Drink, drink, drink. Dance, dance, dance. Fun. Then it's. It's bedtime. So what happens when you're in your little closet and you're doing your little dance where you're trying to put on your pajamas and she's trying to put on her full length nightgown that goes up to her neck and you guys are like trying to work.

[Host (possibly Birch)]

She's trying to get all Amish, right?

[Jeff]

And you guys are trying to work your way around that tiny little room and then you go to bed. Is it like, okay, good night and shake hands or kiss? Or do you try to make two people fit in one bed? Or what happens?

[Richard]

Yeah, actually the state room is a lot larger than I thought it'd be. Oh, yeah, There was quite a bit of room. It was definitely awkward hanging out that much with someone that you don't really know.

[Host (possibly Birch)]

Sure.

[Richard]

It wasn't that bad. I gave her her space. I'd go off, you know, do something else while she got ready and I'd come back. So it wasn't too bad.

[Jeff]

And she was in bed with the sheets pulled right up to her neck tightly.

[Host (possibly Birch)]

Yeah. The first night with another guy.

[Richard]

With someone else.

[Jeff]

So. But then what it is is like, are you guys lying in your separate bed and you go, good night? And she goes, good night.

[Richard]

Yeah, kind of like that.

[Host (possibly Birch)]

It was okay. Could you tell during that first death, I still feel like we're missing here the first day that you guys are out cruising and you're drinking, you're lounging around and stuff. Are you getting any kind of sense at all that there's any kind of chemistry here? Or you do, you know, like right off the bat, okay, this is going to be nothing but friendship?

[Richard]

I think right off it was, let's just see if we get to the first day chemistry.

[Jeff]

Give me a drink.

[Richard]

Unknown. There was a lot of drinking maybe to get through that, but I think by the second day we realized this isn't really, you know, we're not really compatible. So.

[Host (possibly Birch)]

So the second day of a five day cruise, you realize that this is not. You're not compatible.

[Wendy]

But are you getting along? I mean, we're getting along. It could be, you know, platonic and fun and hanging out and looking for other people while you're on the ship together and having a good time.

[Richard]

Definitely. And you know, I would say she was definitely a great pick because she was a lot of fun, she had great personality, she was definitely someone that could.

[Jeff]

All the guys loved her.

[Richard]

Yeah. So, yeah, a good choice. However, not something, you know, long term compatibility. But that wasn't really what I was looking for. I mean, ideally, sure, but I just needed someone to hang out with on the cruise and have fun and she definitely was that person.

[Jeff]

Do you acknowledge that halfway through the second day or are you like, yeah, this isn't going to be anything romantic, so you be my wing woman, I'll be your wingman. Or are you like, let's just drink until we're hot and we'll have sex or what is.

[Richard]

No, there's no sex. It was pretty much, hey, this is how it is, you know, cards on the table, let's just have a good time, make the best of this.

[Host (possibly Birch)]

You said that or she said that.

[Richard]

I brought it up and she confirmed.

[Host (possibly Birch)]

Okay, so you weren't feeling any kind of vibe. If she was vibing on you, would you have been vibing on her?

[Richard]

I don't know.

[Host (possibly Birch)]

Not sure.

[Richard]

It's hard to say.

[Host (possibly Birch)]

So this is day two in a five day cruise. So those other three days, are they on a scale of one to ten, with ten being the best time you've

[Jeff]

ever had in your life.

[Host (possibly Birch)]

It's a Mentos commercial. And one being just awful.

[Richard]

I'd say it's about a four.

[Host (possibly Birch)]

Four.

[Richard]

Oh, you know, it's the Caribbean, you gotta have some fun. But fortunately, at formal dinner, we had dinner with Bill and Ann, who was a fun married couple out of Ohio. And we hung out with them.

[Jeff]

Bill and Ann from Ohio are like the most boring people on the planet.

[Richard]

Hey, be nice.

[Host (possibly Birch)]

She's on the phone.

[Wendy]

She said she's on hold.

[Jeff]

I'm not saying she is. I'm just saying you're. Hi, I'm Ann. This is my husband Bill. We're from Ohio. And I'm like, oh, great.

[Host (possibly Birch)]

It just sounds very geriatric. Is what you're saying. I mean, generic.

[Jeff]

Wow, that is a nice looking cat on your sweater.

[Wendy]

It's great.

[Host (possibly Birch)]

And it's 94 degrees out. All right, so you sit down to this formal dinner and you make friends with other people and things are going okay there.

[Richard]

Right?

[Host (possibly Birch)]

All right.

[Richard]

Yes. And they were very cool, Jeff.

[Jeff]

No, I'm not saying that they're not. I'm sure they are.

[Wendy]

It was a dog on a sweater.

[Jeff]

I'm just saying Bill and Anne from Ohio wear reindeer ears during Christmas season when they go to the mall. Reindeers, hats.

[Richard]

All right, so I think that helped get us over the hump because it was like, okay, we realize this isn't really going anywhere, but sorry about that. So, yeah, we hung out with them most of the rest of the cruise and they made it a lot more fun.

[Host (possibly Birch)]

Okay, we need some honesty here. Because if things are just platonic and you're having a good time and she's having a good time, and you get back to Atlanta, that's a seven. That's an. It was an average trip. Look, I didn't get any. But we had a good time and I'll never forget it. Something happened to bring it from a seven to a four.

[Wendy]

Did you fight?

[Jeff]

Did she hook up with another dude?

[Richard]

I got kicked out of the stateroom the last day. That was awkward. No, I'm just kidding. No, she didn't know it was.

[Jeff]

Did she hook up with another guy?

[Richard]

No, not that I know.

[Host (possibly Birch)]

There was never any kind of argument?

[Richard]

No.

[Host (possibly Birch)]

Any kind of dislike?

[Richard]

No.

[Host (possibly Birch)]

But it was a four. A four is a bad trip.

[Wendy]

It is bad.

[Richard]

Okay, maybe it's not a 4. Maybe it's a higher than that, but 4.2. Yeah.

[Jeff]

Why isn't she on with us?

[Richard]

She had a meeting today so she couldn't get out of it.

[Host (possibly Birch)]

Why Is she really not on with us today?

[Richard]

That's the truth. You call her and ask her.

[Host (possibly Birch)]

I can't. She's in a meeting.

[Jeff]

She can't.

[Richard]

She won't talk.

[Host (possibly Birch)]

We did. We tried. Here's Anne from Ohio.

[Richard]

Hey, Ann. Hi.

[Host (possibly Birch)]

How are you?

[Ann]

Just for the record, I don't want cats on my sweater.

[Host (possibly Birch)]

And what did you see? Because he said, like, the highlight of this trip was hanging out with you and your husband. So what did you see with these two?

[Ann]

Of course. We're fun people. Come on. We're Ohio State Buckeye fans. We know how to party. Come on, gator chomp.

[Host (possibly Birch)]

We'll see. So tell us about the night that you guys hung out with Them. Could you tell that there was zero chemistry going on there?

[Ann]

Well, we met them the first night at dinner, and, you know, they could have totally played it off as a normal couple and we wouldn't have known anything. But the first question I asked was, what made you decide to take a cruise? So they had to tell us the whole story about how they met on the radio and everything. So everything was out in the open from the beginning.

[Host (possibly Birch)]

Okay.

[Ann]

And, yeah, by the second night, we could kind of tell that it probably wasn't going to work. Just not much chemistry. And, you know, we tended. My husband and I tended to carry the conversation a lot. So we just kind of. We're wondering how the conversation was going when we weren't around.

[Host (possibly Birch)]

Was there a lot of conversation going on at all when they weren't around?

[Richard]

Not really.

[Host (possibly Birch)]

Nothing.

[Richard]

That was the worst part.

[Wendy]

That's the worst. It is when you're in a car and you don't know what to say, and both of you are sitting there, it's the longest drive ever. That is the feeling. Because my thought is, if you acknowledged it. If you acknowledged it, nothing was gonna happen. Then that could have been a potential for such a fun trip that's out of the way. You know what? She knew she came on last minute because you and your girlfriend didn't work out because that ended up. You could have had more fun with her than you would have your girlfriend if you'd been fighting the whole time.

[Host (possibly Birch)]

Unless it's just some person that even platonically, you wouldn't even hang out with, even as friends. This is somebody in the office that you have nothing in common with, so you've got nothing.

[Richard]

I think we're just two different people.

[Jeff]

Did she at any point, say on the cruise, I'm not coming back on the radio?

[Richard]

No, she was still planning on it, I think, until the end, where she conveniently had a meeting.

[Host (possibly Birch)]

Okay, so. And you guys were assigned the same table, so you guys ate with each other every night?

[Richard]

Yes.

[Host (possibly Birch)]

I see. So did the relationship slowly deteriorate in front of you, or. It just.

[Ann]

It was just never even there after the second night. It pretty much tended to get worse and worse. And, I mean, we had a fun time and we talked at dinner, but then we started hanging out a little bit more out on the ship and stuff. And then it got more and more awkward as the cruise went on.

[Jeff]

So, like, what was awkward? Just big stretches of silence or, like, were there. Was it like. You ever been out with a couple who starts fighting? I know Bill And Anne don't have any couples that fight. But if you did, like, you know how sometimes and you know, the other couple's fighting, but they're not acknowledging that they're fighting. But it's just like, hi, Wendy, may I have the salt if you're not doing anything else, like our neighbor, please.

[Wendy]

Did they just look miserable?

[Richard]

No.

[Ann]

I mean, it wasn't really fighting, but it kind of got to the point where we would go and do something and Christy would sit on the left side of me, and then my husband was the other side, and then Richard

[Jillian]

would sit on the other side of me.

[Ann]

So they would sit separate from each other.

[Host (possibly Birch)]

So you guys were separated by two people?

[Richard]

Yeah.

[Host (possibly Birch)]

Okay. But there was never an argument or a disagreement. It was just like.

[Richard]

There really wasn't. We actually got along the, you know, times we were talking. Okay.

[Ann]

Yeah, yeah.

[Jeff]

Did. Do you think they ruined your vacation?

[Ann]

Absolutely not. We had a great time. We had fun. I mean, they're both really, really cool people. I mean, Richard was really funny and, you know, he just wanted to have a good time. He's, you know, he's a total gentleman, and any woman out there would be lucky to be with him. So if there's any single ladies listening, you know, if I had. If I knew anybody, I would set him up in a heartbeat because he's a sweet guy. And, you know, it's just one of those things that just didn't work out. And it's.

[Host (possibly Birch)]

It was almost an impossible scenario. I mean, you talk about a long shot. What are you looking like that for me?

[Wendy]

No, I'm just listening. I'm listening because there is an. I just feel like it's a. If there's no tension, if there's no true awkwardness, I just feel like it's a. I don't know, I feel. I don't know, I feel like it's a wasted potential fun time. Even though very well constructed sentence was there one day where you just didn't see each other. You woke up in the morning, didn't see each other all day, and saw each other at night?

[Richard]

Not the whole day, but yeah, near the end, there were some spaces. She didn't show up for dinner one night, so really?

[Host (possibly Birch)]

Really, she just bailed.

[Richard]

She was, you know, tired.

[Host (possibly Birch)]

Did she tell you that she was gonna crash in the cabin or she's just not show?

[Richard]

Yeah, she said she's going back to the cabin and she just didn't show up for dinner. Okay.

[Wendy]

All right.

[Jeff]

That's weird.

[Host (possibly Birch)]

Well, the whole thing is Weird.

[Jeff]

Like the fact he doesn't even show up. Like, I mean, he still is footing the bill for it.

[Wendy]

Yeah, I just. Was it established that there was never gonna be anything going on on the trip or was there always the potential? Because I feel like if there was always the potential and she was just trying to avoid it. Avoid it.

[Richard]

I mean, I think at first there was the unknown, and then a few days in it, it was, you know, we had to talk and.

[Host (possibly Birch)]

And that should have been it.

[Wendy]

That should have made it fun. Okay.

[Richard]

And it was from that point on where she started sitting on the opposite side of our friends.

[Host (possibly Birch)]

Oh, really? After you had that talk? But you say you're. And you're the one that initiated the conversation.

[Richard]

Well, I just brought it up and said, hey, you know, let's talk about what's going on. And we agreed it was awkward and that there's no chemistry and, you know, let's just have a good time.

[Host (possibly Birch)]

Okay, cool.

[Jeff]

At that point, I'd just be like, the hell with it. Deuce in your own bathroom. No need to go down to the bar.

[Host (possibly Birch)]

Thanks, Anne.

[Jeff]

I mean, you're paying for it.

[Host (possibly Birch)]

Bye. Bye.

[Richard]

Thanks, Anne.

[Host (possibly Birch)]

Ann.

[Ann]

Yeah.

[Host (possibly Birch)]

Goodbye.

[Richard]

Bye.

[Ann]

Thanks.

[Jeff]

Anne's on a soap opera. Bill and Ann from Ohio. They're on Young and the Restless. They don't say goodbye.

[Wendy]

The whole conversation's been awkward.

[Host (possibly Birch)]

I think that's right. I want some space. I want some more space between you and me right now.

[Wendy]

I'm uncomfortable.

[Jeff]

I gotta be honest with you. I think the problem in your relationship with Christy was Anne. She's definitely into you, which made Bill uncomfortable, but nobody knows this, but Bill's actually. Bill and Anne are actually swingers. They have a dungeon in their basement.

[Host (possibly Birch)]

It's the ones that you never think would be swinging or really swinging.

[Wendy]

They wear cat sweaters. They don't swing.

[Jeff]

That's just to cover up cat sweaters. But they got cover the sweaters in the summertime to cover up our fierce nipples. Totally, Richard.

[Host (possibly Birch)]

You tried.

[Richard]

I tried.

[Host (possibly Birch)]

At least you tried, man. At least you tried. Yeah. You had an experience.

[Richard]

It was an adventure.

[Host (possibly Birch)]

You'll never do it again, that's for sure.

[Richard]

I don't recommend a five day cruise as a second date, but it was fun.

[Host (possibly Birch)]

Probably not even going to call her. No, probably not. Okay. The Birch Show. I mean, think about what that must feel like. Like that. That anxiety pit in your stomach when you realize that you just got off a date or you just hooked up with your boss's ex and you can't

[Wendy]

do Anything to take it back. I mean, you can't change it history of what you just did. And so, yeah,

[Host (possibly Birch)]

all sorts of angles probably to take it this. Do you tell the boss? Do you let it go? Do you pretend it never happened? Hey, Jillian, you're on the voice disguiser.

[Jillian]

Oh, good.

[Host (possibly Birch)]

Hi.

[Jillian]

Good morning.

[Host (possibly Birch)]

Morning. How are you?

[Jillian]

Good, how are you?

[Host (possibly Birch)]

We're okay. You're on the voice disguiser. We can't recognize your voice.

[Jillian]

Yeah, thanks for pointing out the knot in the pit of my stomach.

[Host (possibly Birch)]

Yeah, I bet.

[Wendy]

Oh, no, tell us the story. How did it happen?

[Jillian]

So I went out. This is past Thursday night. So we went out with some girlfriends. We were just hanging out, drinking. I got a little tipsy at this bar and I met this guy and so I was drinking a little bit, but I actually really did like him. And I know I did something kinda. Kinda slutty. But I ended up going back to his place and hooking up with him,

[Jeff]

like all the way.

[Wendy]

Hooking up?

[Host (possibly Birch)]

Yeah. Let's define hooking up.

[Jillian]

Sleeping with him.

[Host (possibly Birch)]

Okay, but sleeping, but not really sleeping. Gotcha. Not on sleep sleep, no cuddling.

[Jeff]

Just so you know, I don't think that was slutty because you were buzzed, so that makes it not slutty. Just for reference.

[Wendy]

Sweet.

[Host (possibly Birch)]

Chad's numbers just went down by dozens.

[Ann]

Oh my gosh, that's awesome.

[Wendy]

Good news.

[Host (possibly Birch)]

All right, so you go to the bar, you get your buzz on pretty good and you end up. Okay. Gotcha.

[Jillian]

Right, so. But the thing is I ended up, I mean, I stayed over and then I got up the next morning and we switched numbers like it wasn't. It was, you know, we actually did like each other. So we had, we had breakfast. I left.

[Jeff]

Hey, it's a courtesy move when you're doing that early morning number switch, write down your name. Also, just generally speaking, that's a good idea, both of you, because if not about 10:30 in the morning, you'll get a hang up call and that's him hearing the name on your voicemail, just so you know.

[Host (possibly Birch)]

True. All right, so continue on.

[Jillian]

So anyways, the next day I'm at work and I get this text from him and it's like, hey, I had a really great time, hope to see you again soon. And then like right after that is the second text that says, so do you know, do you feel awkward at work today? And I wrote back and I was like, no. Works cool. Why? And then I didn't hear anything back from him until later that night. And he called me to Tell me what was going on. And I had absolutely no idea that this is my supervisor's ex husband.

[Wendy]

So did I miss something that had happened? He knew that you were his ex's employee.

[Host (possibly Birch)]

Yeah. I feel like I missed something here.

[Jillian]

Yeah, but I. Okay, first of all, I have. It's not like I just have one supervisor. I have six supervisors.

[Host (possibly Birch)]

But how did he know that you were an employee of one of those six supervisors?

[Jillian]

Well, apparently, he met me almost three years ago when he was still married at a company event.

[Wendy]

I know you didn't remember him.

[Jillian]

I don't remember him telling me that.

[Host (possibly Birch)]

And he never brought it up when you guys were at the bar getting your buzz on.

[Wendy]

Of course not.

[Host (possibly Birch)]

Never said anything.

[Wendy]

Oh, he was chosen to go there.

[Jeff]

Well played by him. Nicely done. Why complicate things with details that may take your mind off the goal at hand?

[Wendy]

Wow.

[Host (possibly Birch)]

Oh, that sucks.

[Jeff]

It's good for him.

[Wendy]

So were you upset with him? Were you ticked off?

[Jillian]

I was stressed out more than. I mean, I'm upset that he didn't tell me because I was in this position. But then. No pun intended. But then he also. I mean, I really like him. I ended up going out with him again.

[Wendy]

You did?

[Jillian]

Yeah.

[Host (possibly Birch)]

Okay, that's gonna change things here a little bit.

[Jillian]

Over the weekend, I went on again. I was. I didn't go out with him. I went out with my friends. I wasn't gonna go out with him. And. And then I ended up going over there again. I really like him. We totally hit it off. And I mean, you know how hard it is to meet somebody.

[Host (possibly Birch)]

When he told you that he had met you previously, was it a little bit like watching the end of the movie the Sixth Sense, where you're, like, putting everything. Oh, yeah, yeah. Did you remember that you met him before?

[Jillian]

No.

[Host (possibly Birch)]

You didn't. You still had no recollection.

[Jeff]

Have you asked him if. Is it possible that you and he talked about your mutual friend on. What was it, Thursday night, the night of the original hookup, but because you were buzzed, you don't remember it? Are you 1000% certain it didn't come up? Not that it makes a difference.

[Jillian]

That's like. That's one of those. It's a little fuzzy, but I don't. 95% sure.

[Host (possibly Birch)]

So what is the question that we're asking this morning? Do you tell the supervisor? Do you not tell the supervisor? I guess we need a little history here also of the supervisor and the ex. Were they married? How long have they been broken up?

[Jillian]

They were married. They've been divorced for two years.

[Host (possibly Birch)]

Two years.

[Wendy]

Okay.

[Jeff]

No need to tell.

[Jillian]

Question is, what I'm asking is, am I. I just want approval that I can. I mean, am I wrong? Can I still see him? And if I. If I can't still see him, I mean, I need somebody to really tell me that I can't. There's no way that that's okay.

[Wendy]

Well, is your boss over it? Has she moved on?

[Jillian]

I have no, I don't talk to. I mean, I barely work with that supervisor. You know, I obviously don't talk to her about my personal life. Personal life.

[Jeff]

Does she have the ability to fire you?

[Jillian]

Yeah, I mean, all supervisors have the.

[Jeff]

But I mean, like, yeah, in our department. Do you not talk to her enough that, like, would she be able to. On Wednesday if, for whatever reason, would she be able to call you in the office and go, I'm sorry, we have to let you go, or would it be somebody else doing that? Because you're saying that she's a supervisor,

[Jillian]

but, like, I've worked there for years. I mean, is she.

[Jeff]

If she's not. If she's not your immediate boss and she's just someone who's above you in the organization, I think you're free and clear.

[Host (possibly Birch)]

Hey, Natasha, good morning. You're part of the Birch show. Go ahead.

[Ann]

I would just say that if, like he just said, if it's not one of her direct supervisors, it's probably not going to come up enough for her to worry about. On top of that, if it's been two years, I would say she's probably well over it. And if she didn't even know, there's no reason for her to be worried about it. I have direct. I have more than one supervisor, too, and I'm not real close to any of them, but something like that, I would highly doubt that one of them could even. That would come up and just say, you're fired because of that. And if they did, the way that the laws are wrote, she could come back and, I mean, that would be the end of that.

[Host (possibly Birch)]

At one point or another, though, if the relationship evolves into something more meaningful, at some point you're going to have to say something because you're going to end up at an office party together or a Christmas party or something, and you'd want to give your supervisor the heads up that look. I don't want you to be shocked. That's uncomfortable tomorrow at the party when

[Jeff]

bringing the ex husband, I think the listeners.

[Wendy]

It just depends on the nature of the relation Their work relationship. I mean, if it is truly one of many supervisors and it's the one supervisor she never sees, then what is the. You know, why would she have any obligation to say anything after two years? But if she is somebody that she has to deal with a lot and the woman's going to find out some other way and it makes it awkward for them? I don't know. I don't know. I think it all depends on the supervisor's state of mind with her divorce.

[Host (possibly Birch)]

You just don't know, though, because your supervisor won't share that with you. If you're an employee most of the time.

[Wendy]

If she's, you know, if she's over it and she's moved on and maybe she's in another relationship, then I don't think she has anything to worry about.

[Host (possibly Birch)]

Jillian, do you know if your supervisor is in a serious relationship with somebody else?

[Jillian]

Not that I know of, but I really have no idea.

[Host (possibly Birch)]

Okay, Justin, go ahead. You're part of the birth show, huh?

[Ann]

Oh, hey, I think she should have

[Host (possibly Birch)]

the other guy tell her supervisor because

[Ann]

he was the one in the relationship, you know?

[Host (possibly Birch)]

So you say it's the ex's responsibility to say. To define what's going on.

[Wendy]

Maybe it depends on if they still talk or not. I mean, they might not be in communication at all. If they are, that would be a great way to solve the problem.

[Host (possibly Birch)]

404-741. Q100. Hey, Jill, go ahead.

[Ann]

I think that she needs to invite the supervisor over the next time he invites her over, and they need to have a bit of a reunion.

[Host (possibly Birch)]

Oh, you're crazy.

[Wendy]

You're so.

[Host (possibly Birch)]

Jerry. That is creating drama right there. Good morning, Patrick. You're on Q100. Hi.

[Ann]

Hi. I was just wondering if there was children involved.

[Host (possibly Birch)]

How does it sway you either way?

[Ann]

I'm sorry?

[Host (possibly Birch)]

How does it sway you either way? Like, let's say.

[Ann]

Well, I mean, I wouldn't want my. My stepchildren's parents to be my supervisor or vice versa, that that would create a problem.

[Jeff]

You're fascinating this.

[Ann]

If there's not children, then there's no history.

[Wendy]

Well, I think. And also, if there's children, they're still in contact with each other.

[Host (possibly Birch)]

Right.

[Wendy]

If they're. If they don't have children, then they don't necessarily have a reason to be in contact.

[Host (possibly Birch)]

Jillian, are there any children involved in this whole thing?

[Jillian]

No, no.

[Host (possibly Birch)]

No kids. Yeah. Most are calling up saying you don't have to say anything. I just do think that eventually you're gonna have to have that talk before he walks in the office or he's gonna pick you up to have lunch one day or something like that. And wouldn't you rather her. No, before. It's a shock and she finds out in front of the rest of the office.

[Wendy]

But you have to remember, they just hooked up Thursday. And they went on one other date. We're talking about two nights, so. Yeah, telling her now would be way jumping the gun on that.

[Jillian]

You know, we haven't even gone on a date. A real date.

[Jeff]

Yeah. You're just hooking up and you're drunk.

[Host (possibly Birch)]

That's totally different. Last call. Good morning, Shandell. You're part of the Burt Show. Hi.

[Jeff]

Hey.

[Ann]

Morning. I think that they should just keep it to themselves because they just hooked up. They're not in a relationship.

[Wendy]

Right.

[Host (possibly Birch)]

So when do you think it's time for you for her to pull. For Jillian to pull the supervisor aside and go. Okay.

[Ann]

If they decide to stay.

[Wendy]

If they decide to what?

[Ann]

To start dating.

[Host (possibly Birch)]

Start dating. So once it gets exclusive, that's the time to bring the supervisor in on it?

[Ann]

Yeah, pretty much.

[Jeff]

Okay.

[Host (possibly Birch)]

All right. Thank you, Jillian. Most are calling up saying you don't owe the supervisor anything, yet you hooked up with the guy twice. Everything's so exciting now. Yeah, of course. You like him so much, but who knows what's going to happen over the next couple of weeks.

[Jeff]

I like him. Especially after seven beers.

[Wendy]

Just don't screw him over, because then he may call the ex wife and say something.

[Host (possibly Birch)]

Handle it delicately. But you don't owe her anything just yet. Okay?

[Jillian]

Okay.

[Host (possibly Birch)]

All right. Thank you for calling the Bird Show.