Brooke and Jeffrey: Second Date Update - Awkward Tuesday: Ex-Expectations

Episode Date: February 2, 2025

Our listeners love dysfunctional relationships so much, we didn't wanna deprive you. Here's a segment from our Full Show feed that may have even more drama than a Second Date Update. Let us know what you think!  One of our listeners is willing to put herself in a very uncomfortable spot for the sake of her kid. We’ll try to help her in a brand new Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

John Stewart is back at The Daily Show and he's bringing his signature wit and insight straight to your ears with The Daily Show Ears Edition podcast. Dive into John's unique take on the biggest topics in politics, entertainment, sports and more. Joined by the sharp voices of the shows, correspondents and contributors. And with extended interviews and exclusive weekly headline roundups, this podcast gives you content you won't find anywhere else. Ready to laugh and stay informed? Listen on the iHeartRadio app,

Apple Podcasts, or wherever you get your podcasts. Dressing. Dressing. French dressing. Exactly. That's good. I'm AJ AJ Jacobs and my current obsession is puzzles. And that has given birth to my podcast, The Puzzler. Something about Mary Poppins? Exactly. This is fun. You can get your daily puzzle nuggets delivered straight to your ears.

Listen to The Puzzler every day on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Welcome. My name is Paola Pedroza, a medium and the host of the Ghost Therapy Podcast, where it's not just about connecting with deceased loved ones. It's about learning through them and their new perspective. I think God sent me this gift so I can show it to the world. And most of all, I help people every single day. Listen to the Ghost Therapy podcast on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts.

$1.4 billion in NFL quarterback contracts, the untold stories behind the biggest deals in football history. I'm A.J. Stevens, vice president of client strategy at Athletes First, introducing the Athletes First Family Podcast, the quarterback series. My co-host, Brian Murphy, Athletes First CEO, and I are sitting down with the agents who have negotiated contracts for Justin Herbert, Deshaun Watson, Dak Prescott, Tula Tunga-Vaioloa, and Jordan Love. Listen to Athlete's First Family Podcast on the iHeartRadio app, Apple Podcasts,

or wherever you get your podcasts. Hey, you found it, the home of the second date update. It's Brooke and Jeffrey in the morning. And thanks for being here on the weekend with us. Seriously. Yeah, welcome to our home. And I know we have a lot of new listeners from all over the world since we've been in the, you know, top 10 charts of podcasts.

Yeah, so awesome. Which is awesome. And if you don't know, we actually are a full radio show. I know. Radio still exists, and we are talking on it. Yeah. It does. And we do a brand new full hour episode every day

on our main feed, Brooke and Jeffrey in the Morning. And we just thought, you know, y'all seem to like relationship drama. We're kind of experts on it, and we do a lot of other segments, including this one, Awkward Tuesday Phone Call. Yes, love it. Yes, juicy.

Yes, seriously, it's not necessarily always a romantic relationship with these. But it's always awkward. Yeah, and tricky. So sit back and enjoy your Awkward Tuesday Phone Call on Sunday. Totally makes sense. Because why not?

It starts right now. You have to sacrifice so much when you become a parent. Yeah. Your body, your sanity, your bathroom alone time. Oh, man. Don't have that anymore. But it's all worth it to see your child happy. Oh, it's so true.

Unless a one in a million type of situation happens like it did to our listener today. Oh. And now she's thinking, maybe my child can be a little less happy as long as I don't have to deal with this anymore. Yikes. That's what she's thinking, but for the sake of her kid, she is going to put herself into a very uncomfortable spot.

Good mom. And we are going to try to help in your brand new Awkward Tuesday phone call right now. It's Awkward. It's Tuesday. It's Awkward Tuesday phone call. Imagine you accidentally run into somebody from your past, but not a good somebody, like your old second grade teacher

or your cool babysitter who taught you how to delete your browser history before mom and dad got there. Shout out. I mean, that is helpful information. This is a person who you don't wanna run into again. You really don't. And that actually happened to one of our listeners, Dana, who afterwards has emailed us for help,

because she does not know how to continue. Is it at the grocery store in your hometown, because that's where it's the worst. Let's find out. Yeah, but you can get away there. This sounds like something where she does not know how to continue. Is it at the grocery store in your hometown? Because that's where it's the worst. Let's find out. Yeah, but you can get away there. This sounds like something where she's not able to get away. Dana, welcome to the show. Hi, thanks for having me.

I really appreciate it. Oh my God, I'm having anxiety for you. Just the thought, I could think of two people that I do not ever want to run into the rest of my life. Well, I've never seen Alexa smile this big because she knows drama is coming. So she's excited. It's not my life this time.

Tell us what's going on. What made you email us? Oh my, I don't even know where to start, but just to give you like a, I just recently moved my family into a new neighborhood. So we're fresh there. Okay, that's exciting. Yeah.

Yeah, it is, but it's also like stressful because my daughter's already having to switch schools. Oh, that's exciting. Yeah, yeah, it is. But it's also stressful because my daughter is already having to switch schools. Oh, for sure. She's nervous about making new friends. Yeah. Yeah. But just remind her that the new kid is always cool in the beginning.

And also remind her the friends that you make when you're young, they really don't last very long. You're not going to lose them all by adulthood. It's fine. Or I don't know, maybe deliver that a nicer way to her. Oh God. Okay.

Yeah, so on her first day of school, she was like, mommy, I made a new friend. And I'm like, awesome. Wow, on day one. That's great news. Thank God. Yeah. So we've been ahead and arranged a play day

over at her new friend's house. And afterwards I go to pick her up and I go inside So we went ahead and arranged a play date over at her new friend's house. And afterwards I go to pick her up and I go inside and I'm walking the entryway and I'm like they had Legos displayed on there. Oh, that's cool. Like full built Lego sets on there? Yeah. And I'm looking at the Legos and I recognize them.

They're the same ones that my ex had on display nine years ago. Whoa, the same model? Exact same. It was like a set. I knew that they were his because I've seen the exact set before on display at his apartment.

Oh my God. Are you saying you're at your ex's house right now then? That's what I think it is because I'm looking around and I see a photo of him. Oh! Oh, god. It really was him? Yep, it's him.

And I'm like, you've got to be kidding me. My daughter's new best friend is the child of my ex. Oh! Oh, what a small world this. Oh, Brooke's dreams have just come true. That would be terrible. I mean, especially like most exes you're cool with, but there's always the one that you just

don't ever want to see again. And it sounds like that's the person for you. Yep. And you're right. It is the worst thing ever because it didn't end well with us. Oh, no. So wait, is he there when you pick her up? Do you see him?

No. Luckily, he was at work that day, and I've only interacted with the mother. Oh my God. Do you bring it up to the mom? I mean, you have to because isn't it gonna be even more awkward if you're like, I know you're husband? You think it's less awkward to be like,

Oh, hey, nice to meet you. Our daughters are now friends. By the way, me and your husband used to be a thing. Yeah, I don't know. I don't know. I don't have an answer. It's just all of that is like my worst nightmare. I see you walk up there and go,

oh, he downgraded and then walk away. No, no, no. I'm not going to make that up. Just let her figure it out. That is so bad. That would be savage. I mean, that's why I'm calling you guys. I'm like conflicted because my daughter's been asking me,

like, mommy, mommy, let's go over there. And I'm like, what do I do? Oh, dang. And now it's the worst scenario possible. If this couldn't get any worse, her friend is having a birthday party. Oh, over at the house, right? And you know that dad will definitely be

at the birthday party. Oh, jeez. Because it's like you could avoid them the other way. And you know, it says like happy hour mingle hour for the adults. Like they have a theme for adults to be there to have a good time too. You can't just drop her off. I mean, at like they have a theme for the adults to be there to have a good time too They throw a fun party

If this guy if this ex was in love with you Do you think he has any idea that you're the mom of his daughter's new friend? I doubt it if you look alike at all or like resemble Just a name right the name or like I mean honestly if people are still in love with their exes they stalk them on Is that what you did? the name or like I mean honestly if people are still in love with their exes they stalk them on social media Is that what you did? No Okay, yeah, I did that was just curious what they were doing. I've done it before yeah So I'm gonna dilemma now because the birthday's coming up in a few days and I need to have a conversation with the wife

Okay I think that's the right thing to do. He's gonna get it all out there. If I was you, I would move to another neighborhood and try again, how many exes can you have? Yeah, did you unpack your boxes? Yeah. My daughter, she loves this new friend, so I really need some help and advice

on what I'm gonna tell the wife and how it's gonna go. Oh, man. Oh, my God. So that's gonna be our job, come up with some advice to give you. Alexis is smiling again. Uh oh. This is so awkward. Juicy. We're gonna figure out how you can talk to your ex's wife.

Ooh. And just let her know that the two of you used to date and now your kids are best friends. Hey. You should be friends too. Oh yeah. I guess is that too that's totally simple. Maybe everyone will be an adult about this. I'm so nervous.

Of course, you want adult stuff to happen, Brooke. Anyway, let's try and do your awkward Tuesday phone call right after this. It's awkward. It's Tuesday. It's awkward Tuesday phone call. As a parent, you want your child to make new friends. Yes, of course. But worst case scenario is if you find out their new friend is the daughter of your

old ex boyfriend. Oh man. The one ex you didn't want to see ever again. Yeah, not the one you want to get back with. Yeah, like the bad one. Thank you for clarifying. That's exactly what happened to our listener, Dana. And now the clock is ticking because there's a birthday party coming up where all of the adults and the parents are supposed to hang out and mingle with each other. And Dana is absolutely terrified of what to do. Yeah, because she hasn't even seen the ex yet.

She's only interacted with the mom of the girl. We don't know if he knows. And a birthday party means that he's gonna be there. Yeah, that is a good question, Dana. Like, what is the percentage that your ex knows this is already going on? Honestly, I don't know, but if I had to guess, maybe 50%.

50. Oh, 50, 50. Yeah, 50, 50. Those aren't good odds. Gosh. Okay, well Brooke, she needs some advice before we call this other mom and basically lay it all out there for her. What do you think Dana needs to keep in mind?

OK, this is the thing. You have to be so casual. You cannot act like it's a big deal. Yeah, so casual, don't even wear pants for this conversation. Keep it laying back and chill. I'm saying when you talk to her, you need to be like, oh my god, so funny. I just realized I know your husband. What a small world. You act unbothered. Unbothered. What do you think of that, Dana? No big deal. Don't know if I can do that because I feel like I'll be lying and acting. Yeah,

that's what I want you to do. Okay, let's give it a try. Give us your best nonchalant like, oh, me and your husband used to date. Oh, what a small world. I believe it. Are you flirting? Me and your husband used to date. Fun fact of the day. No, no, no, no.

You sound a little bit excited about it. Yeah. Fun fact. More like silly, funny, coincident story, no. You sound a little bit excited about it at that point. Yeah. But you know what? More like silly, funny, coincidence story, not fun fact. What a coinkydinky. Oh, okay. Maybe call it a feisty fact.

Coinkydinky. Yeah, we'll just take a little nugget from that and try and sprinkle it in. I thought that was gonna be good and now I'm more stressed out. Anyway, just do you. I think just be you and you're gonna be good. Oh, well thank you. Yeah, she could've done that without us Jeff. Well

Her fault for calling it recording just tell us how this goes later So here we go I'm gonna dial the other mom and let you talk to her so you can let her know that you used to date her husband Oh my well pray for me. I'll pray for me Okay, we will as I'm dialing the number now. Good luck We'll jump in if we feel like you need help. Hello. Oh, hi. Is this Alex? Yes, it is. Who's this? It's Delilah's mom. Staying at.

Oh, hi. How are you? Oh, I'm good. You know, just getting some things done around the house. How are you? I'm good. I can't complain. I'm just getting ready for this party we have in a few days and I'm definitely not prepared. Oh my gosh. I know how that goes.

Well, bless your heart. What can I do for you? Is everything okay? Oh my gosh, I know how that goes. Well, bless your heart. What can I do for you? Is everything okay? Yeah, so this is, okay, sorry. I'm trying, I wanted to call you and discuss something with you. I had a few parents call about food allergies.

Is that what this is about? Oh, no, no, thank God she doesn't have any food allergies, but I'm calling you because I just kind of like an awkward thing. So I don't know how to sugarcoat this, but it involves your husband. Oh, my husband. Yeah, so please like, don't worry. He's not like cheating on you or anything. But I don't know if you know this or if he's told you,

but the other day, you know, picking up Delilah and I realized after going to your house that I actually know your husband. And we used to date. Yeah, and you don't seem surprised by this. I mean, shoot, he's not looking to date now, if that's what you're wondering. We're married, so... Okay, hold on, hold on. I'm married too, so, you know, I don't know how much he's told you.

We kind of had, like, a weird breakup. So I'm just feeling a little uncomfortable. Do you feel this way? Because you still have feelings for him or? I'm genuinely confused. No, no, no, no. No, why it's like an hour or anyone would be uncomfortable. Like, I mean, he's told me all about you. Okay. So, you know, he told you about this.

Yeah. He said it was a really, it was a really hard hard breakup when you got dumped He didn't want to hurt you Yeah, I mean I'm a woman first. I totally get it. No, he first of all, I didn't get dumped. I dumped him Honey everybody gets dumped. It's okay. It's no need to be embarrassed. It's nothing to be embarrassed about. Oh, wow. Okay.

What? I mean, I haven't, but I can imagine the pain of getting dumped. Wow. No, no, no, no, no. That's not what happened. And I know Danelle comes with it and you have nothing to worry about. Our daughters, they like each other. We can kind of leave it at that.

You need to understand, I dumped him like he was just awkward and resentful after that. And like, this is not cool. Okay. Do you like see a therapist at all? Or have you ever considered that? Definitely. You definitely should. Okay. Wow. Wait, what is all this? Yeah. That's the sound of an entire morning show being on this phone call with you because you're on the radio right now, Alice. Hey, Alice. Oh my god.

We're broken Jeffrey in the morning. We're trying to help out Dana with this awkward conversation that she was trying to have with you about your daughters and the dating history between them. So she goes on the radio? Okay. Well, she wanted advice, but that's not the advice history between them. So she goes on the radio? Okay. Well, she wanted advice, but that's not the advice we gave her. We were expecting you to be surprised by the news that Dana had a relationship in the past with your husband. Because it was definitely a surprise to Dana.

Oh yeah, no, my husband and I talked already. We know what's going on. Like she's someone of the past and I just, I feel like she may still be a little hurt. I'm not hurt, Alice. I'm just calling you to let you know that we were dating just in case you didn't know and then you say I was lying or hiding something from you.

He was like a complete loser after. Okay, well, again. Okay, here's the thing, Dana. It feels like Alice is maybe being a little bit more of the adult here. Yeah. But she's lying. Okay. Well, again. Okay, here's the thing, Dana. It feels like Alice is maybe being a little bit more of the adult here. Yeah. Yeah.

But she's lying. They're lying. That's like, that doesn't make me feel comfortable to come over to their house. Okay. No matter who broke up with who. Yeah, you're a married woman. It was nine years ago.

You found a husband. You had the kids. You did the dream. Cause couples that lie together stay together. That's the saying. Well. Okay. Okay, so just now that you know, Alice, can we like move forward from this? What's the I mean, we already moved forward. If you are involving the radio and you have all these feelings and yeah, all these things going on in your mind. I just want to make sure you're okay, because we're definitely okay over here. Okay, so Dana, I guess guess balls in your court here cuz it sounds like Alice has known about the past relationship And has no concerns about it as long as she doesn't want my husband

Dana can you verbally acknowledge that you are not interested in Alice's husband? I am NOT interested in your husband husband I am not interested in your husband so when the birthday party happens are you comfortable now going over there Dana you know I think for this birthday party I'm just gonna drop her off and have you guys do and maybe we can just have a one-on-one after something and just I just want our girls to be able to play together and get to know one another like that's all that matters I was seems like the most chill go with the flow mom Dana I think that maybe we should go see therapy Yeah, I think it's good chance for you to go over to the house for the birthday party

You can be the better person walk in there write a note and put it under the husband's pillow saying just to be clear, I broke up with you. Just so it's straight. No, I don't want to be petty, but that is a good idea. Oh, okay. Sticky notes. They're nice and small. You won't see him until it goes to bed. Brooke and Jeffrey in the morning. John Stewart is back at The Daily Show and he's bringing his signature wit and insight straight to your ears with The Daily Show Ears Edition podcast. Dive into John's unique take on the biggest topics in politics, entertainment,

sports, and more. Joined by the sharp voices of the show's correspondents and contributors. And with extended interviews and exclusive weekly headline roundups, this podcast gives you content you won't find anywhere else. Ready to laugh and stay informed? Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Dressing.

Dressing. Oh, French dressing. Exactly. Oh, that's good. I'm AJ Jacobs, and my current obsession is puzzles. And that has given birth to my podcast, The Puzzler. Something about Mary Poppins? Exactly.

This is fun. You can get your daily puzzle nuggets delivered straight to your ears. Listen to The Puzzler every day on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Welcome. My name is Paola Pedroza, a medium and the host of the Ghost Therapy podcast, where it's not just about connecting with deceased loved ones.

It's about learning through them and their new perspective. I think God sent me this gift so I can show it to the world. And most of all, I help people every single day. Listen to the Ghost Therapy Podcast on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. $1.4 billion in NFL quarterback contracts. The untold stories behind the biggest deals

in football history. I'm A.J. Stevens, vice president of client strategy at Athletes First, introducing the Athletes First Family Podcast, the quarterback series. My co-host Brian Murphy, Athletes First CEO, and I are sitting down with the agents who have negotiated contracts for Justin Herbert, Deshaun Watson, Dak Prescott, Tula Tunga-Vaioloa, and Jordan Love. Listen to Athlete's First Family podcast on the iHeartRadio app, Apple Podcasts,

or wherever you get your podcasts.