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Brooke
Hey. Welcome to a new episode with the Brooke 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 and how we don't match our voice, but if you want to 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
Alexis Carter
listening on Spotify and paused so fast to go watch on YouTube and now I'm heading back to Spotify.
Jonah
Okay.
Jose
I wonder if it's different to watch us and the or just to listen. Maybe you should do both.
Brooke
Well, it's like reading a book and then going seeing the movie.
Alexis Carter
Oh, the movie is never as good. Yeah, Movie's never as good.
Brooke
No. Yep. So there it is. That's your warning at Brick and Jeffrey. Your new episode starts now.
Jeffrey
They say two's a party, three's a crowd.
Jose
Heard that.
Jonah
Yeah.
Jeffrey
Unless that third person is a waiter coming to your table with a special surprise.
Brooke
What?
Zepbound Ad Speaker
Huh?
Jeffrey
A big one.
Jonah
Hey.
Jeffrey
A big one Surprise.
Brooke
Oh, okay.
Jeffrey
And that's what one of our listeners had planned for her boyfriend. But now that waiter might need to wait.
Jose
Wait like wait wait.
Brooke
Not wait on the table?
Jeffrey
Not wait on the table like wait.
Brooke
This is getting a little confusing, Jeff.
Jeffrey
Yeah, I will.
Jonah
Okay.
Jeffrey
Cause something weird happened the other day and now the whole surprise could be in jeopardy.
Brooke
Oh, okay. We could have started with that that's
Jeffrey
why she's turned to us for help in your brand new awkward Tuesday phone call. Just wait. Cause it's coming up right after this.
Jose
It's awkward.
Brooke
It's Tuesday.
Jose
It's awkward Tuesday phone call.
Jeffrey
If you want to do something nice for somebody special in your life, does it have to be a surprise?
Brooke
No.
Jose
No. But it's nice when it is. Yeah.
Jeffrey
I mean, it is fun. That's true.
Jose
Yeah.
Jeffrey
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.
Brooke
Yeah. Surprises on you, Jeff. I'm still here.
Olivia
Yeah, she is.
Jeffrey
Unfortunately.
Brooke
Yes, that is true. Backfired surprise.
Jeffrey
But that moment was priceless. I wouldn't change that for the world.
Brooke
Yeah, I totally believed you.
Jeffrey
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.
Brooke
Oh, well, sometimes that happens.
Jeffrey
Yeah.
Brooke
You know, like if they want to plan something else. And it's a day that you have this.
Jose
Anyway, it depends on the person, too, right?
Jeffrey
Let's get more details before we start speculating. Olivia, welcome to the show.
Olivia
Hi. Thanks so much for having me.
Brooke
It sounds like you're a really thoughtful girlfriend. Someone who plans something for their boyfriend. Nice job.
Jeffrey
Maybe a surprise breakup. That'd be kind of cool. Very thoughtful. Yes. Good girlfriend. You are.
Olivia
Surprise.
Jose
You're single.
Jeffrey
Anyway. Sorry.
Brooke
Breakups are a surprise. Yeah.
Jeffrey
Sorry.
Jonah
What?
Jeffrey
So what's going on with you and your boyfriend?
Olivia
So we've been living together for five months now, and it's almost his 30th birthday, which I'm so excited about.
Jose
Dirty 30.
Brooke
Is he a birthday guy? What's his name, by the way?
Olivia
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.
Jose
You know, for sure.
Jeffrey
He's definitely not excited.
Jose
Yeah, you're excited to an extent.
Jeffrey
Who's excited to turn 30 when you're in your 20s?
Brooke
I would say nobody. I wish I could argue with Jeffrey, but 30 is the only one I cried at.
Alexis Carter
I don't know, saying that it was
Brooke
just like, such a moment.
Jeffrey
But you feel like maybe he's looking forward to it.
Olivia
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.
Brooke
Okay. So what do you. What do you have planned?
Olivia
Well, so Jonah and I have never really traveled anywhere significant together. We've done like a day trip here and there, but nowhere big.
Brooke
Okay.
Harley Davidson Ad Speaker
Okay.
Olivia
So a friend of mine who works in travel, she's helped me plan a big 30th getaway to Mexico for him.
Jeffrey
Oh, wow.
Brooke
You're gonna take him to Mexico as a surprise trip?
Alexis Carter
That's. So how are you gonna pull that off?
Brooke
I'm so excited for both of you.
Jose
That's why.
Jeffrey
Yeah, I'm thrilled, too, by the way. Sorry. I'm not jumping in all over it, but you can tell.
Jonah
Wow.
Jeffrey
Mexico. Sorry, I grew up in. We went to other places.
Brooke
Oh, sorry.
Jeffrey
But Mexico's cool.
Jose
Over Mexico on the way to other cool places.
Jeffrey
Yeah, I know. Southwest does like a budget trip there. It's really nice.
Brooke
You're such a.
Jeffrey
No, what am I. I'm saying it's great. It's wonderful. This is the best gift anyone has ever given anyone.
Brooke
Ignore Jeff, how soon is this surprise trip supposed to happen?
Olivia
It's going to be coming up, like, 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.
Jeffrey
Wow. So it's like the waiter's idea to send you, and it's not yours. Give him all the credit.
Brooke
Wait, is the waiter coming with us? Like, what's happening?
Jeffrey
That's kind of cool.
Jonah
Cool.
Jose
You got to take them to Mexican food, too. Like, put it in the flan, you know?
Brooke
Oh, that's a good point.
Jeffrey
You definitely plan this whole thing out,
Brooke
though, it sounds like. So what's happening? That's derailing the plan.
Jose
Yeah. What's wrong?
Olivia
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.
Brooke
Oh, no. You think he saw it?
Olivia
Yeah, there's no way he didn't see it.
Jose
And your computer doesn't have, like, an automatic shut off thing?
Brooke
Yeah, like a sleep mode.
Olivia
Yeah, no, I mean, I. 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.
Alexis Carter
Okay, yeah, maybe you have 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.
Jose
You know, I can't look at this.
Alexis Carter
Yeah, that's.
Brooke
I mean, but it's a good move on his part not to bring it up, not to ruin the surprise.
Jose
It's also true, like kind of protecting your feelings.
Jeffrey
Well, I don't know how he acting after that.
Olivia
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. You know, super excited to go to dinner, but let's just keep it low key and that'll be really fun.
Brooke
That makes me think he didn't read the whole thing then.
Alexis Carter
Because if you saw you book stuff, why would you say that you don't
Jose
want to go to cancel?
Jeffrey
That's like the polite way of being, like, I don't know any plans, but if there are plans, not do them.
Alexis Carter
Yeah, I think I get it, but that's so rude. If you saw how detailed the itinerary is. Like, that's.
Brooke
Maybe he's just really bad with secrets and he's like, I know. I'll tell her that I. I don't want her to do anything, and then she won't think that I saw it.
Jeffrey
Yeah, you know, I mean, there's a lot of speculation. What are you feeling right now, Olivia?
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.
Jose
Oh, man.
Brooke
What do you want to do right now?
Jeffrey
What advice are you looking to get from us for this phone call?
Olivia
Okay, 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.
Brooke
I know. It'd be a red flag for me too, because if you'd 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.
Jose
Yeah. My parents are kind of the same.
Jeffrey
Yes, we're all over the spectrum. This is either great or not great. Or somewhere in the middle.
Jose
What if he's worried about money like he thinks, oh, God, I don't know where I have a whole big bill now or something like Mexican trips.
Alexis Carter
Are you saying you have the rest of your 30s to stress about money
Jeffrey
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.
Jose
It's awkward.
Brooke
It's Tuesday.
Jose
It's awkward Tuesday phone call.
Jeffrey
Is there anything worse than when a person knows a big surprise is coming so they fake it just to appease you?
Jose
Oh, they faked a surprise?
Jeffrey
Yeah, that's what happened yesterday when Brooke announced she was pregnant for the third time.
Brooke
I am not pregnant.
Jeffrey
We all knew it was coming and we just had to fake pretend that we were shocked.
Brooke
I am not pregnant.
Jeffrey
Jose even burst into tears just to make Brooke feel better about it.
Jose
Well, that was for different reasons.
Brooke
I went to Dr. Snip and stayed in the room when it happened for my husband. Okay, I know I am not pregnant.
Jose
What? Do they snip on you?
Jeffrey
Yeah. So Dr. Snip is apparently the father, but just a really sad moment all around. That's what our listener Olivia is trying to avoid because her live in boyfriend has his 30th birthday coming up and she wanted to surprise him with a special trip to Mexico.
Jose
Yeah, that's so cool.
Jeffrey
Problem is, he might kind of already know because of a little computer missing mishap. And even worse, if he does know, he doesn't seem all that thrilled about it.
Brooke
In fact, he's basically telling her, all I want to do is dinner, cancel everything else.
Jose
Yeah, low key birthday.
Jeffrey
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?
Brooke
Okay, we're gonna double down on the lie. Oh, things are gonna get a little messy here. But I think what you have to do is you have to say, okay, I'm gonna let you in on 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?
Alexis Carter
Oh, this is the asking for a friend situation. Yeah.
Brooke
Okay, and then just let him answer and he'll tell you exactly what you need to know.
Jose
All right.
Jeffrey
Basically stealing the plot from Lindsay Lohan's Parent Trap. A little double trouble action. What do you think, Olivia?
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.
Jeffrey
Speaking of not paying attention, Jose, what's your advice? What advice? For Olivia?
Jose
My advice would be bring up that there could be a surprise at dinner.
Olivia
Oh.
Brooke
Just tell him and then gauge his
Jose
reaction to that news.
Brooke
Okay.
Jeffrey
Don't be specific about the surprise, but
Jose
you'll be able to tell if he already knows based on his reaction.
Jeffrey
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?
Jose
Yeah.
Olivia
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.
Jose
So he's like, I hate surprises. Then you'll know.
Olivia
Yeah, dump them.
Brooke
Not dump them, but change the ticket to your best friend's name.
Alexis Carter
Yeah, that's good.
Jeffrey
You're right. 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 gonna dial your boyfriend right now and we'll find out what he knows. All right, good luck dialing right now.
Jonah
Hello?
Olivia
Hey, how's it going?
Jonah
Hey. Oh, sorry, I don't know. Your number didn't show up normal. It's like weird. It came like block call or something.
Olivia
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 gonna be able to swing by the store to pick up the chicken for dinner?
Jonah
Yeah, yeah, I can do that. Well, yeah. This afternoon? Yeah. On the way home?
Olivia
Yeah. Yeah, that would be great.
Jonah
Okay. Yeah.
Olivia
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.
Jonah
You okay? You sound a little nervous or maybe distracted or something. You want to call me back later?
Olivia
No, no, no, no, no, no, I'm good. I honestly, I'm a little like excited but anxious for your birthday coming up.
Jonah
Oh, yeah.
Olivia
Okay. Well, I think dinner. I think that dinner is going to be amazing.
Jonah
Yeah, no, it should be amazing. I mean, as long as I'm not cooking it.
Olivia
Obviously I'm not going to make you cook your birthday dinner, but I'm thinking maybe there little surprise at dinner too. What? You. How yeah.
Jonah
Oh, yeah. I mean, you know, you don't have to do anything big. You know, it's not that big a deal.
Olivia
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.
Jonah
Okay. Don't tell me too much. I mean, it's kind of defeats the purpose of it being a surprise, right?
Olivia
Well, I didn't tell you what it is, but.
Jonah
No, don't tell me what it is. You got to keep a secret.
Olivia
Okay. I mean, I don't really feel like you seem that excited about dinner or the surprise at this point, so. Is that because you already know what it is?
Jonah
No. I mean, I don't know. Maybe. Do I?
Olivia
Okay, so you saw my computer in the itinerary. Oh, What? Oh, I knew this. I knew this is what happened. So you already know that the day after dinner, I'm taking you to Mexico.
Jonah
What? Oh, no, I did not know about that.
Olivia
You just said you knew.
Jonah
You just said you knew. No, I said maybe. I. Like, maybe. Maybe I didn't see your computer. Well.
Olivia
Surprise. We're going to Mexico after your birthday.
Alexis Carter
When?
Jonah
Well, no, we're not.
Olivia
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.
Jonah
No, I. I can't go. I'm on the no Fly List. Wait, hang on here. Who is. Who's on the phone? Hey, what is going on?
Jeffrey
Hey, Jonah. This is a radio show called Brooke and Jeffrey in the Morning. Olivia's a listener.
Brooke
If we're not calling from the tsa, do not worry.
Jonah
Oh, no, no, no, no, no.
Jeffrey
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.
Olivia
Yeah, I'm sorry. Nobody cares about that right now. You're on the no Fly List? How did you not know this?
Jonah
I'm sorry I didn't tell you. I just didn't think it was important right now.
Brooke
Why are you so chill right now?
Jeffrey
Yeah, are we talking to a terrorist right now? How are you on the no Fly List?
Jonah
I didn't know I was going to be on the radio. I don't know if I really want to tell everybody.
Jose
Is it embarrassing? I want to know more.
Brooke
I'm curious how you get on one.
Jonah
Yeah, I thought it's Like I thought, it's pretty embarrassing.
Olivia
You need to explain this right now. Like, how in the world does one get on the no Fly list? This is insane.
Jeffrey
And that's puts you on the spot, Jonah, but I feel like this information needs to be out there, at least for your girlfriend's sake.
Brooke
Well, and for everybody else, so they can avoid doing what you apparently did.
Jonah
Yeah.
Jeffrey
How do you. How did you get on the list?
Jonah
Well, I mean, we had all been drinking, right?
Jeffrey
And who's we?
Jonah
My buddies and I. Frankie and Joe and Chris.
Jeffrey
Oh, duh.
Jonah
Yeah, obviously a bachelor trip, you know, bachelor.
Brooke
How long ago was this bachelor trip?
Jonah
Maybe a year ago.
Jeffrey
So what happened on this bachelor trip that landed you on a national no fly list?
Jonah
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.
Jeffrey
Wait, you're doing stuff on a beverage cart?
Jose
Or did you say in the beverage cart?
Jonah
Yeah, on top and around it. Oh, I don't want to talk about it. I definitely regret it.
Alexis Carter
How long can you not fly for?
Jonah
No, they just gave me time out for like a couple years or something. I don't know.
Jeffrey
Oh, my God, you're so casual about it, dude.
Jonah
Well, I mean, I was really tossed, man.
Olivia
Okay, you can't fly for another year.
Jonah
Oh, well, give or take. I think it's like two or three years. Yes.
Jeffrey
So, Olivia, this is obviously a lot of information coming your way. How are you feeling? Where's your head at?
Olivia
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 milestone for your birthday. So I. I'm not even, like, sure how to process this yet.
Jonah
I mean, we could drive somewhere. We could go. We could go to Canada.
Brooke
What? Why do I have a feeling that there's something on your record that will not let you into Canada?
Jonah
I'm sorry, babe. You know, listen, this happened over a year ago and we were just barely talking. You know, I'm a different guy now.
Brooke
Oh, he's immature. 30 year old.
Jose
That's right. That's right.
Olivia
Yeah. I think I'm going to choose to believe that that's true for now because other than this, had no reason to think otherwise. So we'll figure something out.
Brooke
How refundable are any of these tickets that you bought or.
Olivia
Yeah, I'm gonna have to find a friend to go with, I guess.
Jose
Oh, no.
Brooke
Okay.
Jonah
Oh, baby. You can't go without me. I mean, it's my birthday.
Jose
Oh, now she.
Jeffrey
Now you're making demands?
Jose
She paid for everything.
Olivia
Yeah, I'm not missing out just because of whatever you did.
Brooke
Sounds like the new surprise is your girlfriend's gonna be out of town for a couple days.
Alexis Carter
Yeah.
Jeffrey
So call Frankie and all the guys and let's get together for just a boys trip.
Jose
Road trip.
Brooke
That is not a good idea. That is not a good idea.
Olivia
Brooke and Jeffrey in the morning.
Jeffrey
I will say that dude has a very, very understanding girlfriend.
Brooke
Oh, I don't know yet. I don't know that she's fully processed.
Jose
Yeah, telling her, I mean, still understanding.
Brooke
I mean, it honestly means they don't get to fly anywhere for the next two to three years of their relationship.
Jose
Like, anywhere? Not even like a local.
Jeffrey
No, but if you found out your significant 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.
Brooke
Do you think he was hiding, though? He just seemed like a dude who forgot to bring it up.
Jose
I swear. We've talked about this before, right?
Brooke
Yeah, I don't know. It just didn't come up.
Jose
Oh, yeah, that's right.
Jeffrey
I am on the no Fly list. I totally forgot.
Jose
I also have a warrant, by the way.
Jeffrey
But she was just like, oh, that's a bummer, and quickly pivoted to going on the trip with her girlfriend.
Brooke
So that was a smart choice.
Jose
Yeah, she should do that right now just to cope. Go to Mexico with your girls, talk it out, relax, reevaluate.
Brooke
If you talk it out with your girls, you're gonna end up single by the time.
Jose
That's probably true.
Jeffrey
Sounds like they're just gonna celebrate his 30th separately, and it doesn't seem like this will be a giant bump in the road of their relationship whatsoever.
Brooke
Yeah, I love when you're not sarcastic.
Jeffrey
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 who's listening to the podcast right now. Stay optimistic. Hit that subscribe button.
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Jeffrey
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Hey, it's Ashanti Plummer from Futaround and find out coming out of the draft, it's been a special time for us here at Futaround. I want to thank everyone from the fans to the sponsors, especially geico. Not just for supporting az, but for showing up where it matters, like the business of Women's Sports Summit. That kind of thing really moves the needle. And now that AZ is starting a new life in Dallas, we don't know what next season is going to bring. But we know that we're all on the same team and it's been amazing to feel the love and support. So keep showing up for our girl. Show up for each other. Thanks to GEICO and our listeners.
Episode: Awkward Tuesday: Surprise Surprise
Date: June 9, 2026
Podcast Host: iHeartPodcasts
In this entertaining episode of the “Awkward Tuesday Phone Call” segment, Brooke, Jeffrey, and the crew help a listener named Olivia navigate a birthday surprise gone awry. Olivia meticulously planned a trip to Mexico for her boyfriend Jonah’s 30th birthday, only to suspect that he may have discovered her secret plans by accidentally seeing the itinerary on her computer. Her dilemma: does he actually know about the trip, and worse, is he even excited about it? The team jumps in to help Olivia get to the bottom of things—and what unfolds is a twisty, hilarious, and genuinely awkward phone call that neither she nor the audience could have predicted.
The episode is filled with playful banter, light jabs, and camaraderie, balanced with genuine concern for Olivia’s feelings. The hosts use humor to diffuse tension, especially as the plot twists into chaos. Their reactions are both empathetic and comedic, making the segment engaging for listeners.
This episode is a must-listen for fans of relationship drama, light-hearted chaos, and classic “Brooke and Jeffrey” wit. The spectacular plot twist and Olivia’s cool-headed pivot offer both laughter and a real-world lesson in managing surprises and expectations.