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Chapter 1: What surprise is Olivia planning for her boyfriend's birthday?
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Chapter 2: How does Olivia feel about her boyfriend's reaction to the surprise?
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They say two's a party, three's a crowd. Unless that third person is a waiter coming to your table with a special surprise. A big one. Surprise. And that's what one of our listeners had planned for her boyfriend. But now that waiter might need to wait. Like wait, wait. Not wait on the table? Not wait on the table, like wait. This is getting a little confusing, Jeff.
Okay, because something weird happened the other day, and now the whole surprise could be in jeopardy.
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Chapter 3: What is the significance of turning 30 in this episode?
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.
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.
It was.
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. Yeah. 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. Yeah.
Let's get more details before we start speculating. Olivia, welcome to the show.
Hi, thanks so much for having me.
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Chapter 4: What unexpected problem arises regarding the surprise trip?
Nice job.
Maybe a surprise breakup. That'd be kind of cool. Oh, wait a minute. Very thoughtful. Yes, good girlfriend you are. Surprise, you're single. 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.
He's definitely not excited. Yeah. 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 is 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.
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Chapter 5: How does Olivia plan to reveal the surprise to her boyfriend?
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 nowhere big.
Okay.
So a friend of mine who works in travel, she's helped me plan a big 30th getaway to Mexico for him.
This is amazing. You're going to take him to Mexico as 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 wild. I'm thrilled too, by the way. Sorry I'm not jumping in all over it. I can tell, Jeff. Wow, Mexico. Sorry, I grew up in, we went to other places. Oh, sorry.
But Mexico's cool.
But we would fly over Mexico on the way to other cool places. Yeah, I know Southwest does like a budget trip there. It's really nice. You're such a party pooper. 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, like, right after his birthday.
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Chapter 6: What advice do the hosts offer Olivia regarding her situation?
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. Oh!
Wow. So it's like the waiter's idea to send 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 flan, 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, does it? 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. Yeah. Maybe he had to shut the screen off to resist reading it.
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Chapter 7: How does Olivia's boyfriend react during the phone call?
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. 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.
Unless he's like, tell her to cancel. 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.
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. 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. I thought Mexico would be great. We've talked about Mexico before, but 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... 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.
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Chapter 8: What is the final outcome of Olivia's surprise plan?
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 an old... Oh, that's not bad. I don't know where I have a whole big bill now or something.
Like, Mexican trips are not... Did he say, you have the rest of your 30s to stress about money?
Not now.
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. We all knew it was coming, and we just had 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 a different reason. I went to Dr. Snip and stayed in the room when it happened for my husband, okay? 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 live-in boyfriend has his 30th birthday coming up, and she wanted to surprise him with a special trip to Mexico.
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