Brooke and Jeffrey: Second Date Update - Awkward Tuesday: Surprise Surprise

Episode Date: June 9, 2026

A HUGE surprise is in total JEOPARDY and Olivia has turned to us for help! We’ll do our best to keep things on track in your Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

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Joy 101. It's a new podcast hosted by me, Hoda Kot me. If you're craving inspiration, support, and useful tools to maximize your joy, tune into these candid, uplifting, and moving on-air chats. Listen to Joy 101 on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I am the Therapy Gecko. I am an unlicensed lizard therapist who takes phone calls from real anonymous humans about their problems, such as this. Sometimes I'll have my girlfriend pre-chew it spicy food and kind of baby bird it into my mouth. Is that weird? This week on Therapy Gecko, we're hearing all real authentic human stories about anything, from relationships to family drama to serendipitous encounters with unexpected,

people and things. If real people pique your interest, this is the podcast for you. Listen to Therapy Gecko on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Michelle McPhee, and I've been unraveling the strangest criminal alliance I've ever reported on, a Mormon polygamist and an Armenian businessman. Multi-million dollar house, Ferraris and Lamborghinis, private jets, a billion dollar fraud. But how long can this alliance last? Tell me what you know. Is somebody coming after me?

Listen to Kingdom of Fraud on the I-Heart Radio app, Apple Podcasts, or wherever you get your podcasts. Last night, a blown call changed a game. This morning, the internet lost its mind. And nobody's telling you exactly what happened. That's where Sports Slice comes in. I'm Timbo. In every episode, we're cutting through the noise, breaking down the biggest moments in sports and giving you the real story behind the headline.

And we're going straight to the source, the athletes themselves. Their locker room stories, their reactions in the moment, and the stuff nobody gets to hear. Listen to SportsSlice on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. And for more, follow Timbo Sliced Life 12 in the TikTok podcast network on TikTok. Hey, welcome to a new episode with the Brick and Jeffrey podcast.

Thanks for being here. And a reminder, we've been doing a video for you all. Go be disappointed in the way we look. how we don't match our voice. But if you wanna see a live awkward or a live second date on video, you can do that on our YouTube channel, at Brooke and Jeffrey. So thank you so much for being here.

We got a new episode, an awkward Tuesday coming up in a second, but comments, Alexis. Carter in color said, I was listening on Spotify and pause so fast to go watch on YouTube. And now I'm heading back to Spotify. Okay. I wonder if it's different to watch us and the order to listen. Maybe you should do both.

Well, it's like reading a book and then go and seeing the movie. The movie is never as good. Yeah. So there it is. That's your morning. At Brick and Jeffrey, your new episode starts now. They say two's a party, three's a crowd. I heard that.

Unless that third person is a waiter coming to your table with a special surprise. What? A big one. A big one. Surprise. Oh, okay. And that's what one of our listeners had planned for her. boyfriend, but now that waiter might need to wait.

Wait. Like wait, wait, wait. Not wait on the table. Like wait. This is getting a little confusing, Jeff. I will, okay, because something weird happened the other day, and now the whole surprise could be in jeopardy. Okay.

We could have started with that. That's why she's turned to us for help in your brand new, awkward Tuesday phone call. Just wait, because it's coming up right after this. It's awkward. It's Tuesday. It's awkward Tuesday phone call. If you want to do something nice for somebody special in your life, does it have to be a surprise?

No. No, but it's nice when it is. I mean, it is fun, that's true. Like when I surprised Brooke the other day and told her she was traded to another radio station for an intern to be named later. Yeah, surprise is on you, Jeff. I'm still here. Yes, she is. Unfortunately, yes, that is true.

Backfired surprise. But that moment was priceless. I wouldn't change that for the world. She'd see Brooks fans. Yeah, I totally believed you. Our listener today, Olivia, says she's been planning a surprise for her boyfriend. But now, thanks to recent developments, she feels like maybe she should just tell him and blow the whole thing. Oh.

Well, sometimes that happens. You know, like if they want to plan something else and it's a day that you have to surprise. Anyway. It depends on the person, too, right? Let's get more details before we start speculating. Olivia, welcome to the show. Hi, thanks so much for having me. It sounds like you're a really thoughtful girlfriend.

Someone who plans something for their boyfriend. Nice job. Maybe surprise breakup. That'd be kind of cool. Oh, wait a minute. Very thoughtful. Yes, good girlfriend you are. Surprise, you're single.

Anyway, sorry. Most breakups are a surprise. That's true. So what's going on with you and your boyfriend? So we've been living together for five months now, and it's almost his 30th birthday, which I'm so excited about. Dirty 30. Is he a birthday guy?

What's his name, by the way? Oh, I'm sorry. Jonah, yeah. And yes, I think he's excited for the most part. You know, I feel like since it's a milestone, it's kind of got that like, I'm excited, but also can't believe that I'm turning 30 feeling, you know? He's definitely not excited. You're excited to an extent. Who's excited to turn 30 when you're in your 20s? Nobody is. I wish I could argue with Jeffrey, but 30's the only one I cried at. I don't know. It was just like such a moment. But you feel like maybe he's looking forward to it?

I think so. I mean, I am, so I think I'm going to be able to make him excited about it if he's not. Okay. So what do you have planned? Well, so Jonah and I have never really traveled anywhere significant together. We've done like a day trip here and there, but no, we're big. Okay. Okay. So a friend of mine who works in travel, she's helped me plan a big 30th getaway to Mexico for him. Whoa. Oh, wow.

That's amazing. You're going to take him to Mexico as a little. a surprise trip. That's so fun. How are you going to pull that off? Dude. I'm so excited for both of you. That's a wild.

Yeah. I'm thrilled too, by the way. Sorry, I'm not like jumping in all over it. But yeah. Wow. Mexico. Sorry, I grew up and we went to other places. Oh, sorry.

But Mexico's cool. Mexico's amazing. On the way to other cool places. Yeah, I know Southwest does like a budget trip. That's really nice. You're such a. No. I'm saying it's great.

It's wonderful. This is the best gift anyone has ever given anyone ever. Ignore Jeff. How soon is this surprise trip supposed to happen? It's going to be coming up right after his birthday. So my plan was to take him out to dinner and then after dessert, I'm going to have the waiter drop off the envelope on the table that has the itinerary on it. And then we would leave the next day.

Wow. So it's like the waiter's idea to start. sent you and it's not yours. Give him all the credit. Wait, is the waiter coming with us? Like, what's happening? That's kind of cool. You got to take her to Mexican food too.

Like put it in the flon, you know? Oh, that's a good point. You've definitely planned this whole thing out though. It sounds like. So what's happening that's derailing the plan? Yeah, what's wrong? Well, okay, so I was going over the itinerary at home and just kind of making sure everything was buttoned up, ready to go.

And I got this phone call from work, which I had to step out to deal with. And while that was happening, Jonah came home and when I got back to my computer it was just off. Oh no. You think he saw it. Yeah, there's no way he didn't see it. And your computer doesn't have like an automatic shutoff thing. Yeah, like a sleep mode.

Yeah. No, I mean, I suppose like maybe he just reached down and turned it off since I wasn't there. But the document was up on the screen. Okay. Maybe he had to shut the screen off to resist reading it. Like if someone leaves their phone out next to you, I'm like, close it so I don't want to read it, you know?

I can't look at this. Yeah. I mean, but it's a good move on his part not to bring it up, not to ruin the surprise. It's also true, like, kind of protecting your feelings. Well, I don't know. How was he acting after that? Well, I didn't bring it up either, but I thought he was acting a little weird. Like, the next day, he just sort of comments like, hey, I hope you're not planning on doing anything too big for my birthday.

Oof. You know, I'm just super excited to go to dinner, but let's just keep it low-key, and that'll be really fun. That makes me think he didn't read the whole thing then, because if you saw you book stuff, why would you? say that because you don't want to go. Yeah. That's like the polite way of being like, I don't know any plans, but if there are plans, let's not do them. Yeah.

I get it, but that's so rude if you saw how detailed the itinerary is. Maybe he's just really bad with secrets and he's like, I know, I'll tell her that I don't want her to do anything and then she won't think that I saw it. Yeah. You know? I mean, there's a lot of speculation. What are you feeling right now, Olivia? I mean, I put a ton of work into this. Yeah.

I thought Mexico would be great. We've talked about Mexico before, but like if he can't even just be excited or appreciate that I put in that kind of work, I'm going to be pretty upset. Oh, man. What do you want to do right now? What advice are you looking to get from us for this phone call? I need a clever way to figure out if he has seen this itinerary or not. I have to know.

And if he did see it and doesn't like it, how do I react to that? Because to me, that just doesn't even bode well for our relationship. I know. It would be a red flag for me, too. Because if you like to travel and he doesn't, that's... I mean, I don't know. My parents have been married for like 40 plus years, and one loves to travel and one is really not.

So maybe sometimes it works out. I guess, yeah, my parents were kind of the same. We're all over the spectrum. This is either great or not great or somewhere in the middle. What if he's worried about money? Like, he thinks, oh, God, I'm in an old... I don't know where I have a whole big bill now or something. Like, Mexican trips are not...

Did he say, you think the rest of your 30s to stress about money? Not that. Or dump him because he's poor. Either way, we support you when we come back and do your awkward Tuesday phone call right after this. It's awkward. It's Tuesday. It's awkward Tuesday phone call. Is there anything worse than when a person knows a big surprise is coming?

So they fake it just to appease you. Oh, they fake the surprise. Yeah, that's what happened yesterday when Brooke announced she was pregnant for the third time. I am not pregnant. We all knew it was coming, and we just had to. to fake pretend that we were shocked. I am not pregnant. Jose even burst into tears.

Just to make Brooke feel better about it. Well, that was for different reasons. I went to Dr. Snip and stayed in the room when it happened for my husband. I know I am not pregnant. So Dr. Snip is apparently the father. Just a really sad moment all around. That's what our listener, Olivia, is trying to avoid

because her living boyfriend has his 30th birthday coming up, and she will. wanted to surprise him with a special trip to Mexico. Yeah. That's so cool. Problem is, he might kind of already know because of a little computer mishap. And even worse, if he does know, he doesn't seem all that thrilled about it. In fact, he's basically telling her, all I want to do is dinner, cancel everything else.

Yes. No key birthday. So she wants to find out for sure, does he know, does he not know, does he even care? Brooke, what's your advice for her? Okay, we're going to double down on the lie. Uh-oh. Things are going to get a little messy here, but I think what you have to do is you have to say, okay, I'm going to let you in a little secret. I'm helping

my friend plan a trip for her boyfriend. And it's a surprise, but she thinks he doesn't want to go. What should she do? Oh, this is the asking for a friend situation. Yeah, okay. And then just let him answer. And he'll tell you exactly what you need to know.

All right. Basically stealing the plot from Lindsay Lohan's parent trap. A little double trouble action. What do you think, Olivia? Okay. I don't know. I'm worried it'll be a little suspicious just because his birthday is so soon, but I don't know. You know how guys are. Sometimes they're not really paying attention to everything, so maybe it'll work. Speaking of not paying attention, Jose, what's your advice?

What? Yeah, advice for Olivia. My advice would be bring up that there could be a surprise at dinner. Oh, just tell him. And then gauge his reaction to that news. Oh, I see. Don't be specific about the surprise. Yes.

But you'll be able to tell if he already knows. Based on his reaction. Okay, what do you think about that, Olivia? Just toss up the idea of a surprise could be coming at dinner and see how he reacts to it. Yeah. Yeah, I think that seems like a good idea because he's not generally a great liar as far as I know. So I feel like if he does know, I'm going to be able to tell. So he's like, I hate surprises, then you'll know.

Yeah. Dump them? Not dump them, but change the ticket to your best friend's name. Oh, yeah, that's good. Okay. We have given you two pieces of great advice you could choose to use. as much or as little of it as you want to, but I'm going to dial your boyfriend right now

and we'll find out what he knows. Oh, man. All right. Good luck. I'm dialing you right now. Hello. Hey, how's it going? Hey. Oh, sorry.

I don't know. Your number didn't show up normal. It's weird. It came like a block call or something. Oh, that's weird. I don't know why it would do that. Sorry. Well, I'm glad you answered.

Do you think you're going to be able to swing by the store to pick up the chicken for dinner? Yeah, yeah, I can do that. Well, what? Yeah, this afternoon. Yeah, yeah, yeah, yeah, that would be great. Okay. I don't know.

I know that's not like the most exciting, but I'm so, work has been crazy. So, yeah, that's all I have time for tonight. You're okay? You sound a little nervous or maybe distracted or something. You want to call me back later? No, no, no, no, no, no, no, I'm good. I, I honestly, I'm a little, like, excited,

but anxious for your birthday coming up. Oh, yeah, okay. I think that dinner is going to be amazing. Yeah, no, it should be amazing. I mean, as long as I'm not cooking it. Obviously, I'm not going to make you cook your birthday dinner, but I'm thinking maybe there will be another little surprise at dinner, too. Oh, yeah?

Oh, yeah. I mean, you don't have to do anything big, you know. It's not that big a deal. I want to do something special. for you. I think it'll be, I mean, you're turning 30. Like, this only happens once and I just think a little extra surprise is in order for your birthday. Okay. Don't tell me too much. I mean, it's kind of defeats the purpose of it being a surprise, right? I didn't tell you what it is, but. No, don't tell me what it is. You got to keep a secret.

Okay. I mean, I don't really feel like you seem that excited about dinner or this surprise at this point. So is that because you already know what it is? No. I mean, I don't know. Maybe. Do I? I don't know. Okay. So you saw my computer in the itinerary. Oh. What? I knew this. I knew this is what happened. So you already know that the day after dinner I'm taking you to Mexico. What? Oh. No. I did not know about that. You just said you knew. You just said you knew. No. I said maybe. Maybe. I like, Maybe I didn't see your computer. Well, surprise.

We're going to Mexico after your birthday. Well, no, we're not. What do you mean we're not? I've literally booked the tickets. I've planned everything. It's like we're ready to go. No, I can't go. I'm on the no-fly list.

What? Wait, hang on here. Who's on the phone? Hey, what is going on? This is wild. Jonah, this is a radio show called Brooke and Jeffrey in the morning. Olivia's a listener. We're not calling from the TSA.

Do not worry. Oh, no, no, no. No, it's okay. This is a segment we do. It's called the Awkward Tuesday phone call. And Olivia reached out because she had this big surprise coming, and she wasn't sure if you knew about it or not. Yeah, I'm sorry.

Nobody cares about that right now. You're on the no-fri-flip. How did you not know this? I'm sorry to tell you. I just didn't think it was important. Why are you so chill right now? Are we talking to a terrorist right now? How are you on the no-fly list?

I didn't know it was going to be on the radio. I don't know if I really want to tell everybody myself. Is it embarrassing? I'm curious how you get on one. Yeah. I thought it's like... It's definitely embarrassing. You need to explain this right now.

Like, how in the world does one get on the no-fly list? This is insane. And that's put you on the spot, Jonah, but I feel like this information needs to be out there, at least for your girlfriend's sake. Well, and for everybody else, so they can avoid doing what you apparently did. Yeah. Yeah. How did you get on the list?

Well, I mean, we had all been drinking, right? Who's we? My buddies and I, Frankie and Joe and Chris. Oh, duh, yeah. A bachelor trip, you know. Oh. Bachelor. How long ago was this Bachelor trip?

Maybe a year ago. I can't remember. You aren't sure. You aren't from flying. So what happened on this Bachelor trip that land? that landed you on a national no-fly list. Yeah. You know, just the normal stuff.

We've been drinking, and things got weird on the planet before you know we're doing stuff on the beverage cart. Wait, doing stuff on a beverage cart? Or did you say in the beverage cart? No, it's just on top and around it. I don't want to talk about it. I definitely regret it. How long can you not fly for?

Yeah, that's important. No, they just gave me time out for like a couple years or something. I don't know. It's funny. No. No. Oh, my God. You're so casual about it, dude.

Well, I mean, that was really tossed, man. Okay. You can't fly for another year? Oh. Well, give or take. I think it's like two or three years. Yes. So, Olivia, this is obviously a lot of information coming your way.

How are you feeling? Where's your head at? I don't even know what to think right now. Like, I put a ton of time into this, and it was supposed to be our first big trip together and celebrating a huge mile. stone for your birthday. So I'm not even like sure how to process this yet. I mean, we could drive somewhere. We could go, we'd go to Canada.

What? Why do I have a feeling that there's something on your record that will not let you into Canada? I'm sorry, baby. You know, listen, this happened over a year ago and we were just barely talking. You know, I'm a different guy now. He's immature 30-year-old. Oh, that's right. That's right. Yeah, I'm going to I think I'm going to choose to believe that that's true for now because I, others than this, had no reason to think otherwise. So we'll figure something out. How refundable are any of these tickets that you bought?

Yeah, I'm going to have to find a friend to go with me, I guess. Oh, no. Oh, baby, you can't go without me yet. I mean, it's my birthday. Oh. Now she can go. You're making demands. She paid for everything.

Yeah, I'm not missing out just because of whatever you did. Sounds like the new surprise is your girlfriend's going to be out of town for a couple days. Yeah. So call Frankie and all the guys and let's get together for just a boys trip. Road trip. That is not a good idea. That is not a good idea. Brooke and Jeffrey in the morning.

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This season, experience Prince Edward County's hottest cultural destination. Explore what's on now at base 31.ca. Joy is essential and it's also elusive. You can't order it, you can't borrow it or simply hope it into life. But now, there's a new and exciting way to start your journey toward a more joyful existence. Joy 101. It's a new podcast hosted by me, Hoda Kotby. Together, guys, we'll have meaningful conversations with the world's most fascinating people. Entertainment legends, sports icons, wellness experts, and everyday people will share how they find, allow, and experience joy.

And I'll offer some of my own tips and takes on seeking a more balanced and harmonious life. If you're craving inspiration, support, and useful tools to maximize your joy, Tune into these candid, uplifting, and moving on-air chats. Joy after a breakup. Joy is an empty nester. Joy after a loss. Joy as a caretaker. This new podcast will speak to you.

Listen to Joy 101 on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I will say that dude has a very, very understanding girlfriend. Oh. I don't know that she's fully processed. Yeah. He's telling her. She's still understanding. I mean, it honestly means they don't get to fly anywhere for the next two to three years of their relationship.

Like anywhere. Not even like a local. No. But if you found out your significant other was on the no-fly list and has been hiding that from you for a year, that might make me question a lot about the relationship. Do you think he was hiding, though? He just seemed like a dude who forgot to bring it up. I swear we've talked about this before, right?

Yeah, I don't know. I just didn't come up. Oh, yeah. That's right. I am on the no-fly list. I totally forgot. I also have a warrant, by the way. But she was just like, oh, that's a bummer and quickly pivoted to going on the trip with her girlfriend.

That was a smart choice. She should do that right now, just to cope, go to Mexico with your girls, talk it out, relax. If you talk it out with your girls, you're going to end up single. That's probably true. Sounds like they're just going to celebrate his 30th separately, and it doesn't seem like this will be a giant bump in the road of their relationship whatsoever. Yeah, I love when you're not sarcastic. I'm just going blind optimism here. And that's what I recommend to everybody who emails the show seeking our advice.

And also to anybody is listening to the podcast right now. Stay optimistic. Hit that subscribe button. Joy is essential and it's also elusive. But now there's a new and exciting way to start your journey toward a more joyful existence. Joy 101. It's a new podcast hosted by me, How to Kot me. If you're craving inspiration, support, and useful tools to maximize your joy,

tune into these candid, uplifting, and moving on-air chats. Listen to Joy 101 on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I am the therapy gecko. I am an unlicensed lizard therapist who takes phone calls from real anonymous humans about their problems, such as this. Sometimes I'll have my girlfriend preach you, it's spicy, food and kind of baby bird it into my mouth. Is that weird? This week on Therapy Gecko, we're hearing all real authentic human stories about anything from

relationships to family drama to serendipitous encounters with unexpected people and things. If real people peak your interest, this is the podcast for you. Listen to Therapy Gecko on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Michelle McPhee, and I've been unraveling the strangest criminal alliance I've ever reported on, a Mormon polygamist and an Armenian businessman. Multi-million dollar house, Ferraris and Lamborghinis, private jets, a billion dollar fraud. But how long can this alliance last?

Tell me what you know. Is somebody coming after me? Listen to Kingdom of Fraud on the I-Heart Radio app, Apple Podcasts, or wherever you get your podcast. Last night, a blown call changed a game. This morning, the internet lost its mind, and nobody's telling you exactly what happened. That's where SportsSlice comes in. I'm Timbo, and every episode we're cutting through the noise, breaking down the biggest moments in sports and giving you the real story behind the headline.

And we're going straight to the source, the athletes themselves, their locker room stories, their reactions in the moment, and the stuff nobody gets to hear. Listen to SportsClyce on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. And for more, follow Timbo Slica Life 12 in the TikTok podcast network on TikTok. This is Michael Rappaport, and my podcast, the I Am Rapaport Stereo podcast, is unlike anyone you've ever heard. If you're looking for strong opinions about sports, entertainment, politics, pop culture, and whatever else catches my attention, then subscribe now. This kid, Jafar Jackson, should absolutely positively get nominated for his portrayal as Michael

Jackson. Listen to I Am Rap Report on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast.