Brooke and Jeffrey: Second Date Update - Awkward Tuesday: Fantasy Fail

Episode Date: March 17, 2026

One of our listeners managed to ruin a LONG TIME friendship with ONE single sentence… He’s ready to risk anything to take it back so we’re setting him up with an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Getting ready for a game means being ready for anything, like packing a spare stick. I like to be prepared. That's why I remember, 988 Canada's suicide crisis helpline. It's good to know, just in case. Anyone can call or text for free confidential support from a train responder anytime. 988 suicide crisis helpline is funded by the government in Canada. In the middle of the night, Saskia awoke in a haze. Her husband, Mike, was on his laptop.

What was on his screen would change Saskia's life forever. I said, I need you to tell me exactly what you're doing. And immediately, the mask came off. You're supposed to be safe. That's your home. That's your husband. Listen to Betrayal Season 5 on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Nancy Glass, host of the Burden of Guilt Season 2 podcast.

This is a story. about a horrendous lie that destroyed two families. Late one night, Bobby Gumpbright became the victim of a random crime. The perpetrator was sentenced to 99 years until a confession changed everything. I was a monster. Listen to Burden of Guilt Season 2 on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Clayton Eckerd. In 2022, I was the lead of ABC's, The Back.

But here's the thing. Bachelor fans hated him. If I could press a button and rewind it all I would. That's when his life took a disturbing turn. A one-night stand would end in a courtroom. The media is here. This case has gone viral. The dating contract. Agree to date me, but I'm also suing you. This is unlike anything I've ever seen before. I'm Stephanie Young. Listen to Love Trapped on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

Good people. What's up? What's up? It's Questlove. So recently I had the incredible opportunity to have a real conversation with an actress and producer, Jamie Lee Curtis, from routines to recovery, true lies, and a certain Jermaine Jackson music video. Jamie's surreal and raw. And it's something I really admire about her. I am so happy that I'm the head bitch in charge at 67, that I have the perspective that I have at my end. age to really be able to put all of this into context. Listen to the Questlove show on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Happy St. Patrick's Day. It's Brooke and Jeffrey.

Yeah. And we've got a brand new episode for you. Yeah. Okay. Who's drunk? I'm walking to you, Brooke. I mean, I wish that I could say that it was two Irish lassies on the phone for your awkward Tuesday phone call today.

But we-thick accents. Yeah, we really miss the mark on that one. Why did we think of that? Yeah. The mercy of the listeners. Yeah, that's true. That's true. We do have an awkward,

brand new awkward call coming up in a second, but first, your comments. Yeah, this one said, my fifth grade daughter came home today and said, did you hear the second date update today? She doesn't have a phone,

but we do share a Spotify duo. So I asked her how in the world she heard it. And she told me she logged into her Spotify at school and listened to it. I can only assume it's because we listen to the red comments every day,

and she heard the one about someone listening in class. Oh, she wanted her inspired her actually. And then a not very happy emoji because, you know, listening in school. So we kind of taught kids how to listen in school. I can't believe

there's a school district that hasn't blocked us on Spotify yet. Yeah, true. Good on you. All right. Thank you for being here. Brand new episode starts right now. There are a lot of sentences that have the power to instantly ruin a friendship. Wow. Yeah, I guess.

Like, I mean, your wedding was okay. It was my favorite. Yikes. Or your parents just told me I'm like the child they never had. Oh, but they already have a child. Oh, yeah. Or I think AJ's a way better backstreet boy

than Nick ever. Oh my God. How dare you? Well, one of our listeners admits he managed to ruin a long time friendship with one single sentence. He can't believe he said it, but he's willing to do anything to take it back.

Oh, goodness. Even come on our show and risk nationwide humiliation. Hey. Can we save his failing friendship? We're going to find out in a brand new Awkward Tuesday phone call. Next. It's awkward. It's Tuesday.

It's awkward Tuesday phone call. Have you ever said something while you were under the influence that came back to haunt you later? Hey, boys. Hey, how you doing? As Brooke would say, what is duh? Yeah, probably all have. The thing is most of the time, people will forgive you for your stupid drunken words. But what if they were so bad, they actually affected your friendships with people?

Oh, yeah. That could pose a problem. And it's why one of our listeners, Joey, has reached out for help today. Very interested to hear about this. Joey, welcome to the show. Hey, thanks for having me. Uh-oh, Joey. Were you the drunk one with dumb words?

You know, I didn't think I was too drunk. I thought at most just a little tipsy, but yeah, definitely an awkward night. Okay. Well, good to know that it actually gets worse than what we're about to hear. And I don't know what was said or where you said it or who you said it to. So set the scene for us. Like, what happened? Well, I was at a friend's birthday party last weekend, you know, at a bar.

And there was probably like 30 people there. I knew most of them. It started going way past midnight. Okay. So everybody's having a good time? Yeah. We shut the place down. Nice. I saw my good friend Vanessa there. We've never been involved with each other. I should say that up front.

Okay. And from what I can remember, it was just a really good kind of heart-to-heart talk. Oh, okay. Yeah. When does the makeout start? No. No. Nothing like that. Just more of like a shoulder to lean on, getting out of a bad breakup and just talking to her about it. Or a shoulder to balance on when you're losing it because you're so intoxicated. Yeah, whose breakup was messy?

Yours or hers? Hers. Hers. Okay. Okay. So she's confiding in you. I mean, that's a good friend. Yeah.

She's been a good friend to me over the years, too. And I remember thanking her for just being so consistent over the past few years. I remember being a nice conversation. Okay. Okay. But clearly you're reaching out to us because it wasn't that nice. Or it sounds like somebody else remembers it different. Maybe. Yeah.

Yeah, apparently, because I didn't think anything of it. And the next day I get a call from one of my buddies who tells me, someone heard me talking to Vanessa, and they heard me say that I had fantasized about her. Whoa. No, you send that to her face? Not like I have a crush on you. Like, I fantasize about you? Yeah, I started freaking out.

Oh, man, that is pretty great. Is there a way they could have misheard you? Yeah, like they were the drunk one? Well, that's what I had hoped because between us, it is true, but I can't believe that I would have said that. Oh, it's true? Yeah. Okay. Just going to like six or seven details about the fantasy so that we know.

No, I think I'll pass on that one. Oh, okay. You're no fun. I got to say, like, I don't know if this is true for Alexis, but for me, like, if a guy said he fantasizes about me, it's like icky. It feels like it's crossed a boundary, especially of a friend. And if she's not into him, it just makes it a little like borderline creepy. Yes. Yes.

That's why I couldn't believe that I actually said that. So I texted her and I asked her if I actually said that. Oh, you just straight out asked her? I just asked her. Oh, honestly, good for you. Wow. We didn't know if it was true. Well, yeah.

Wow. I figured if I couldn't remember she would. Yeah. Okay. I mean, yeah. And what was her response? Well, she did remember and she said yes that I did. Oh, no.

Yeah. And hopefully you didn't go into detail, right? I didn't get that far. I just immediately started apologizing and she told me to just stop. Okay. So it's not something that you actually wanted her to know. It just accidentally slipped out and that was embarrassing. I feel terrible.

I mean, one stupid comment, the friendship's ruined. And the timing couldn't be worse. Like she just went through this terrible messy breakup The last thing she wants to do is deal with another guy You know like you were supposed to be her friend in that moment And that was the opposite of what you were Yeah, I I feel like I'm piling on it And I didn't mean to

Yeah, you're a bad guy and you're creeping all your friends out What's wrong with you? I get it I get where he feels bad about it Yeah What is your goal here? Just to salvage your friendship? Yeah, so 100% I'm not trying to have anything romantic

I just need help giving us back to place we were before. That's actually good news because you're never going to get back to a romantic spot with her, but we could totally get a friendship back. Totally. It sounds super easy. Be like, I'm not attracted to you at all. Okay.

Well, why do we even need to give advice when Jeff's here with that? Yeah. Yeah, that would be great. Just say psych and we'll hang up and it'll be all over with it. Easy. I hope that's not your actual advice because I really do. I'm trying to joke. Geez, you're so picky about the advice that you want to get on this.

Come begging. But okay. Okay, I'll think of something new. So what are you trying to tell her? I just want to tell her. I'm sorry, and it was a stupid thing to say. And I was not in my right state of mind. And I want us to stay friends.

Okay, so I guess that's why you need some backup support. We'll all be like, it's totally true. He has zero interest in you romantically. He just wants to be friends. What if Jeff and I out creep her so much? It makes you look good. That's an idea. Yeah.

But that's not much of a challenge for me and Jose. You're right, Jeff. I did it in one sentence. You're right. Like a couple of sentence ago. So did I. So it's really up to you, though. We'll come back.

We'll give you a little bit of advice. Get a female perspective. That would help, Brooke. Yeah, that's on the female. Sorry. Yeah, the female in the room if she could contribute. And then we will come back and let you make your awkward Tuesday phone call. Oh, boy.

To your friend to be like, I am sorry for saying that I fantasized about you. Oh, man. It just hits so weird. Don't say the sentence more. Just one time, though. It was only once and never again. We're going to do it with your awkward Tuesday phone call right after this. It's awkward.

It's Tuesday. It's awkward Tuesday phone call. This is a great example of why word choice matters. Oh, yeah. There's a difference between telling your friend years ago I had a crush on you. Versus years ago, I had a fantasy about you. Those feel very different. different.

It's funny because you could have a crush for a year, and that's okay. But one fantasy for 30 seconds is like, ew. Yeah, it just hits way thickier. And unfortunately for our listener, Joey, he said that second one, drunkenly to his friend, Vanessa. And I don't think he added the years ago. That would make it better, actually. Yeah. Well, I'm assuming it wasn't that night, Joey, right?

No, not that night, no. Oh, okay. Maybe a week, a week before. It's still a general term. The thing is he doesn't even remember saying it to her, but it has been confirmed by multiple sources. Including her. Yep. Since someone else at that party overheard it and then word got around.

So no surprise ever since. Things between Joey and Vanessa have been very uncomfortable to say the least. And Joe needs our advice here on how to apologize and walk back what he said to reassure her. It was just a dumb, drunken slip up and all he wants is to be your friend. So, Brooke, what do you think Joe should do here? Well, I think right now, Joe, we need to concentrate on what you didn't do. What didn't I do? Okay, what you didn't do is you didn't inappropriately make a move.

Okay. You didn't pressure her to go out with you. You didn't try to kiss her. Like, you respect her as a friend. You respect your boundaries. And you just made a really dumb, embarrassing statement. Very well said. You're right.

I don't think I did any of those things. I would love it if you would have said I didn't do it. Yeah. He did all three. I thought you said you were tipsy. Yeah. But it's a good idea to be like, well, I could have kissed you, but I didn't do that. No, don't say that either.

So, kudos to me. That doesn't count great. Good advice, Brooke. Jose, what do you think? Well, we all had a group cring when you just said the word fantasize. And I think you should try to use the word fantasize in other areas of your life. You try to normalize it. Thank you, Brooke.

Like, for example, you say, hey, do you have any lunch plans? because I've been fantasizing about this salad all week long. It's just a verb you use all it time. Yeah, what's the big deal? I hate that I love this advice. Joey, what do you think? If I'm being honest, I kind of feel like the more I use that word, the more it's just going to make her think about me saying it.

Oh, man, I've been fantasizing about that advice for like two songs. Come on, man. I might never use the word fantasize ever again. Okay. Maybe that's a promise you can give to Vanessa if we're able to get her on the phone. phone here. So I'm going to dial her number. You have that advice in your back pocket, but hopefully she picks up and we'll let you make your awkward Tuesday phone call. You feel ready? I think so. All right. Oh boy. We're here to back you up if you need us, but I'm dialing the number

right now. Here we go. Hello. Hey, Vanessa, it's Joey. Okay. What are you doing? I'm calling you because I don't want things to be awkward between us. Um, I mean, I mean, it is, though. And I don't even know if we should be talking right now. Listen, we've been friends a long time. And it was a dumb thing to say, but it was just one dumb thing. It was just words. I didn't try to kiss you.

I didn't do anything inappropriately. I didn't make a move or anything like that. It was just a dumb thing to say. Yeah. And just by the way, I didn't do any of those things, right? Okay. No, no. Thank God, you didn't.

Okay, well, you don't have to go overboard about it. I mean, that would have definitely crossed an even bigger line. Well, are you hearing what I'm saying? I really feel bad about it. I mean, I'm losing sleep over here. It's not good. Okay, look, just really did not know what to say in that moment, and it really caught me off guard, especially because I just got out of a relationship.

It just wasn't really something I was prepared to hear. I don't want to picture you picturing me that way, and, you know, put yourself in my shoes here. I mean, I'm trying to. That's why I'm trying to get things back to how they were and saying I'm sorry about saying, such a dumb thing. I know, but not only did I just get out of relationship, but, I mean, come on, we're also related.

Wait, what? Related? Yeah, yeah, she's my step-sister. That is a big, important word. Wait, that doesn't make it better? It makes it okay. No, it doesn't. It's okay to fantasize about your steps.

And it really depends on when the parents got married. Oh, God. Justify that. Vanessa, I'm sorry. Are you there? What is happening right now? I am so confused.

Well, my co-hosts are justifying why it's okay to fantasize about your step-siblings, but what we're doing is called an awkward Tuesday phone call. Oh, my God. And it's really awkward. Joe did not tell us that you were his step-sister. No. Not at all. I didn't think that it was important to mention to you guys.

You know, it's not like we lived together. She didn't become part of the family until I was already out of the house. Oh, see? Better. Holy God. It would have been a good piece of information for us to have going into this call. No wonder she's weirded out. Yeah, honestly, that's a very important piece of info.

But it also makes sense while your parents are attracted to each other. Brooke. You're the one standing up. You're from Idaho, so I get it. We already justified it a little. He was an adult when his dad or mom married the other person. I don't know. Oh, my gosh.

excuse in my mind, but... This is probably the most uncomfortable phone call I've ever had. My advice to him was almost like, why don't you pursue it? So now I'm glad. Oh, wow. I mean, I was really going back and forth on apology or... Oh, wow.

She still has that stance. I don't. I don't. Oh, my God. Joey. Hey, I'm with Brooke. It's not that weird to just think it. It's weird to act on it, maybe, but not to just think it. It's weird to talk about it, too. Oh, no. I'm not. I never had step siblings, but if I got a stepbrother as an adult, I mean, who'd be?

Yeah, look out. Exactly. Oh, my. Okay. We need to get back to the problem at hand. The whole reason that we made this call, Vanessa, is because Joey feels terrible about what he said. He does not believe that, right, Joe? Yes, I believed it once, but not anymore.

He's not interested in you romantically in any way at this point in time, and he really shouldn't be. When he said that, I was kind of. pressed a man said that on the phone, but now it needs to say. Yeah, now it's a very low bar that we're trying to clear. Joey, talk to her, please. Yeah, this is a huge thing to leave out. I just, I didn't think it was an important detail. I thought the main thing was just trying to tell you that I'm sorry and I never should

have said it and I will never say it again. Can you forgive me? I mean, yeah, Joey, like, I forgive you. You know, I'm not going to completely cut you out of my. life or anything. I just, I think I just need like a minute, a long minute to really process this whole situation. Brother Ick is a different level of it. So I totally get it's a process. I mean, if it was in my family, people would be making fun of you, Joey, for like the next 10 years of your life. Maybe your whole life for this. Like it would be an on running joke in our family for sure.

That's true. You know, maybe something we'll laugh about in the future. Just treat this as a dumb thing that we said once. And we. Well, me. Fine, me that I said once. And then we can go get lunch together because I have been fantasizing about a salad. Oh, my God. That's funny how you think it's kind of like still a joke?

I don't know. Eventually, maybe I'll probably be able to laugh about it in the long future. Maybe. All right. Yes. All right. Well, at least see a Christmas? I mean, yeah, I'm not going to miss Christmas.

He's already thinking about Christmas? He just can't wait to see you again. Okay. Oh, man. It sounds like you're going to need to give her some space, Joey, and just let her process it and get over it on her own time. Yeah, and I'd recommend no alcoholic beverages for you at any family functions in the future. Yeah, definitely not at Christmas. Yeah, that's probably a good idea.

Great. Okay. All right. I feel like this is a successful, awkward Tuesday phone call that we've done. Yeah, bringing family real together. Yeah. Oh, my gosh. Oh, my God, my sister's calling me right now.

Should I answer? What do you think she wants to talk about? Why don't you fantasize about it? Oh, Joey. That's his real sister. Brooke and Jeffrey in the morning. Getting ready for a game means being ready for anything. Like packing a spare stick.

I like to be prepared. That's why I remember, 988, Canada's suicide crisis helpline. It's good to know, just in case. Anyone can call or text for free confidential support from a train responder anytime. 988 suicide crisis helpline is funded by the government in Canada. In the middle of the night, Saskia awoke in a haze. Her husband, Mike, was on his laptop. What was on his screen would change Saskia's life forever.

I said, I need you to tell me. exactly what you're doing. And immediately, the mask came off. You're supposed to be safe. That's your home. That's your husband. To keep this secret for so many years, he's like a seasoned pro.

This is a story about the end of a marriage. But it's also the story of one woman who was done living in the dark. You're a dangerous person who prays unvulnerable and trusting people. Your predator, Michael, love, and good. Listen to Betrayal Season 5 on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. This is going to be kind of crazy to say, but I think we may have actually helped. I think we did.

Oh, my God. They needed to talk. I know. And Joey was just going to keep digging himself a deeper and deeper. whole if we didn't intervene. And honestly, if he would have told us it was his step-sister, would our producer have even picked his email as someone to help? I mean, our producer does love chaos.

So, yeah, he'd probably throw us into that. I do love, though, that our help at the end of the day was still like, I just need time and I'll hit you up later, bro. Yes, that and also, Brooke normalizing fantasies about family members. So thank you for that, Brooke. They're adults when they got introduced to each other. I mean, come on, Jeff. Yeah, sure.

I have a few websites that you're going to love, by the way, Brooke, if that's how you think. Like I said, I never had step siblings, so maybe I'm off. You've watched Clueless, though. So I've watched Clueless, and they fall in love at the end, and it's like the cutest ending. That's a perfect point. Some stepbrother. You need to hop on the stepboard. I know.

What's wrong with me? I'm just glad that we're all good now, and they're just going to take their time and let the relationship men naturally. As families do. But it doesn't happen all the time. Sometimes you need us to jump in and intervene. and if that's where your life's at, email the show. We can help you with whatever awkward situation you're dealing with. Make sure to hit that follow, subscribe button.

If you're listening to the podcast, like us, rate us, and comment something about your step-s sibling. It's a weird ass. Yeah, I don't know. In the middle of the night, Sasquia awoke in a haze. Her husband, Mike, was on his laptop. What was on his screen would change Saskia's life forever. I said, I need you to tell me exactly what.

you're doing. And immediately, the mask came off. You're supposed to be safe. That's your home. That's your husband. Listen to Betrayal Season 5 on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Nancy Glass, host of the Burden of Guilt Season 2 podcast. This is a story about a horrendous lie that destroyed two families. Late one night, Bobby Gumpright became the victim of a random crime. The perpetrator was sentenced to 99 years until a confession changed everything. I was a monster. Listen to Burden of Guilt Season 2 on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Clayton Eckerd. In 2022, I was the lead of ABC's The Bachelor.

But here's the thing. Bachelor fans hated him. If I could press a button and rewind it all I would. That's when his life took a decision. disturbing turn. A one-night stand would end in a courtroom. The media is here. This case has gone viral. The dating contract. Agree to date me, but I'm also suing you. This is unlike anything I've ever seen before.

I'm Stephanie Young. Listen to Love Trapped on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Good people. What's up? What's up? It's Questlove. So recently, I had the incredible opportunity to have a real conversation with us. Actress and producer, Jamie Lee Curtis, from routines to recovery, true lies, and a certain Jermaine Jackson music video. Jamie's real and raw. And it's something I really admire about her.

I am so happy that I'm the head bitch in charge at 67, that I have the perspective that I have at my age to really be able to put all of this into context. Listen to the Questlove show on the IHeart Radio. app, Apple Podcasts, or wherever you get your podcasts. Ready for a different take on Formula One? Look no further than No Grip, a new podcast tackling the culture of motor racing's most coveted series. Join me, Lily Herman, as we dive into the under-explored pockets of F-1, including the story

of the woman who last participated in a Formula One race weekend, the recent uptick in F-1 romance novels, and plenty of mishap scandals and sagas that have made Formula One a delightful, decadent dumpster fire for more than 75 years. Listen to No Grip on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.