Brooke and Jeffrey: Second Date Update - Awkward Tuesday: Unhappy Birthday

Episode Date: September 9, 2025

One of our listeners THOUGHT his girlfriend was planning an epic birthday trip for him, until one text message shattered everything… and now he needs an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Hi, my name is Enya Umanzor. And I'm Drew Phillips. And we run a podcast called Emergency Intercom. If you're a crime junkie and you love crimes, we're not the podcast for you. But if you have unmedicated ADHD... Oh my God, perfect. And want to hear people with mental illness, psycho babble. Yes, yes.

Then Emergency Intercom is the podcast for you. Open your free IHeartRadio app. Search Emergency Intercom and listen now. Do we really need another podcast with a condescending finance brof trying to tell us how to spend our own money? No thank you. Instead, check out Brown Ambition. Each week, I, your host, Mandy Money, gives you real talk, real advice with a heavy dose of I feel uses. Like on Fridays when I take your questions for the BAQA.

Whether you're trying to invest for your future, navigate a toxic workplace, I got you. Listen to Brown Ambition on the IHeart Radio app, Apple Podcast, or wherever you get your podcast. What would you do if one bad decision forced you to choose between a maximum security prison or the most brutal boot camp designed to be hell on earth? Unfortunately for Mark Lombardo, this was the choice he faced. He said, you are a number, a New York State number, and we own you. Listen to shock incarceration on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Every case that is a cold case that has DNA right now in a backlog will be identified in our lifetime.

On the new podcast, America's Crime Lab, every case has a story to tell, and the DNA holds the truth. He never thought he was going to get caught, and I just looked at my computer screen. I was just like, ah, gotcha. This technology's already solving so many cases. Listen to America's Crime Lab on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Dr. Scott Barry Kaufman, host of the psychology podcast. Here's a clip from an upcoming conversation about how to be a better you. When you think about emotion regulation, you're not going to choose an adaptive strategy which is more effortful to use unless you think there's a good outcome.

Avoidance is easier. Ignoring is easier. Denials easier. Complex problem solving takes effort. Listen to the psychology podcast on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. It's Tuesday, which means it's your awkward Tuesday podcast. If you're on the second date update,

I mean, awkward Tuesday for us is really kind of like second date in that it's a relationship oriented, but it could be any relationship. Yeah. But today we do have a boyfriend and a girlfriend that are having issues. We do. Which is, you know it's always good when they call a radio station to talk. They help them communicate.

If I was dealing with what this guy was dealing with, I would have lost it a lot sooner than he did, a lot sooner. So you're going to hear that. in just a second, but we love to highlight your comments. Yes, Libby said, I only listen to you guys in the car, and no, I'm not changing it for anyone. Oh, wow.

Do you think she listens to the podcast or the radio in the car? I don't know. You know, I read it first as radio, and then I'm like, maybe not. Maybe not. That's so interesting. Yeah, we are on the radio, just so you guys know. That is well. All right, let's get into your podcast.

It starts right now. Imagine thinking you just won the lottery. only to find out two months later it was a weird computer glitch and you actually won nothing. No way! That's what it's like getting hired to work in radio.

Yay! Oh, wait a second. Oh, come on, Jeff. You love working with us. Sure. But there is one non-radio person who understands the feeling all too well because our listener

thought his girlfriend was planning the most epic birthday trip for him of all time until one text message shattered everything. Oh, no. And now he needs our help not to save the trip, but possibly to save his relationship. You're going to hear it in a brand new Awkward Tuesday phone call. Next.

It's awkward. It's Tuesday. It's awkward Tuesday phone call. Do you like it when a significant other makes a big deal about your birthday? I love that. Like goes through the effort to plan things for you. buys you nice presents, does a big surprise. Yes.

I mean, Brooke says she loves it, unless the surprise is a barbershop quartet. That was uncompy, okay? That was not cool. Okay. But there are contingencies to the surprise, clearly. Well, four weird old men standing behind me singing in a radio studio, it's not my idea of a good time.

How do you know they're weird? Kind of an inside joke, but if you didn't know a while ago, Brooke's husband organized that for her on the show. and she absolutely despised it. Dude, just making eye contact with people that are singing to you is just too much for me. I wish I was here for that. Oh, my God.

Anyway, I bring it up because one of our listeners, Croy is having a birthday soon and his significant other was making a big deal about it. Emphasis on was. Uh-oh. Because it sounds like maybe things have changed. Croy, welcome to the show. Hey, guys, thanks for having me. Oh, man.

I'm sorry. When's your birthday? It's coming up? Yeah, yeah. 30th birthday's coming up in a few weeks. And you're in the doghouse? Like, you're in trouble? It's literally dirty 30. Like, but not dirty in like a fun way. Okay, so what made you email the show for help about your birthday, something with you and your girlfriend? What's going on?

Yeah, yeah. So my, I've been seeing my girlfriend, Chrissy, for two years now. Thank you. And months ago, she started making a big deal about how she wants to go over the top for me for my 30th birthday. Aw. Cute. That's awesome. That's a great girlfriend.

Yeah, what does that mean, though? Well, it means that she got me an early birthday present, which was a really nice watch. Oh. And in addition to that, for the actual birthday, she booked us a trip to the Bahamas. Wow. That's insane. Oh, my gosh. You didn't take the watch as, like, kind of an insulting present, though.

Wait, what do you mean? Like, you're running out of time. You're hitting 30? Like, yeah, you're never on time for stuff. Oh, on time. Now you're getting old, times running out. You didn't read into it like that. Symbolic.

No, maybe if it wasn't as nice to watch as this, but I mean, I didn't even think about that. Oh, she really splurred. So, I'm going to give you a Rolex, are you calling me old? Wait, are you calling and there's a, like, you have an upcoming Bahamas trip, right? Well, yeah. But, I mean, even more than that, it's not just the watch on the Bahamas trip. She even showed me that she splurged on the hotel room, too. Like, we have a super nice view.

of the ocean that's amazing she bought us outfits for the trip to wear when we go out so wait where is the problem come in so the problem comes in that last week she tells me that she had to return my watch what wait what uh-oh yeah and i was like oh why i really like this watch it's really nice and she said i know but maybe we'll get you a different one later uh-oh and i was like what does that mean? And she was like, I don't really want to talk about it. Oh, bummer.

I immediately think maybe she overspent. Yeah. Yeah. You know, like, as it sounds like she was just going nuts, like the hotel room and the trip and the watch, and then she got the credit card bill. And she was like, wait a minute.

I went too far. And we could do that with a watch, but we'll still do the vacation. Yeah, yeah. Yeah. Well, my thoughts are worse because after that happened last week, She texted me yesterday saying that she had to cancel the trip.

What? No. Now Bahamas are off the table too? Yes. What are you thinking? I think she's planning to break up with me. Oh. Really?

Oh. Yeah. No, she's not planning to break up with you. You're a good guy. She wait out the breakup though. I wouldn't she just... Because she wants to get the refund first. Maybe she...

She doesn't want to spend the money. I don't know, but I would feel the same. Because why else would you do that? Like, why can't he's rebook? You can't do Cleveland instead of, like, the Bahamas? Sure, even if it is too expensive, you can find a more affordable alternative. I think more than anything, why no explanation? Why isn't she telling you?

Have you asked her what's going on? When I kept asking her why, she was like, oh no, we'll do a different thing. We'll do a different thing later. Later. And she usually brings things up to me if something's on her mind or whatever, but this has been different. and I'm like, I can't think of anything other than she's going to break up with me, and I don't know why. I have no idea why.

Oh, man. That's tough. Like, I think I'd be pissed. Yeah. I'm just thinking, if my boyfriend gave me these big, grandiose things and then took them away, I'd be like, what the hell? Like, I would probably be the one thinking about dumping them, to be honest. Yeah.

He better be taking it back to plan something better. Oh. Like, you take away presents that have already been gifted. Is that your suggestion to him right now? He should dump her first before she dumps him? No, no, no, no. Well, maybe. Depending on what she has to say.

Well, I'm not that shallow, and really I'm just more concerned about our relationship here. No, that's good. That's good. You seem like a really good guy. I mean, aside from taking away all your birthday presents and canceling your birthday trip and then not communicating about her feelings about why, is there any other red flags in the relationship that we should have? Yeah, none that I can think of. Okay.

That's good. Well, then we need to help you figure out what the heck is going on. With your girlfriend and your birthday plans coming up, there has to be an explanation. I need her to open up and tell me because it seems like anything I say, she quickly just closes it down. She doesn't want to talk about it at all anymore. We could just call a bunch of like Chucky Cheeses and see if there's any bookings coming up. You think she could still be planning a surprise? There's got to be a surprise from the surprise.

I don't know. It seems like the birthday is, like, far away in her mind, too. Like, she's not even planning anything anymore, you know? Okay, so we have a mission now to find out why after your girlfriend booked a vacation for your 30th birthday and got you an expensive watch, she took it all back with zero explanation. That's intense. We'll try to get you some answers in your Awkward Tuesday phone call. Thank you, guys. Next.

It's awkward. It's Tuesday. It's awkward Tuesday. What are the subtle red flags from a significant other that show they're attempting to break up with you? Oh, man. Maybe if they change your Netflix profile name to just the word guest. Oh, ow. Why did that hurt?

That's not a good sign. Just crying in the opening screen? Wait, you're still in the profile. Sort of. You still have access. Or if you find a PowerPoint presentation on their computer about why you should start seeing other people. Oh, that is very. specific. It's a red flag, not saying it's totally over yet.

Who's is this? Could have helpful information in it. That's true, too. And the only things our listener, Croy has noticed from his girlfriend are she's returned his birthday gift without asking him, canceled his birthday vacation, and hasn't been communicating about why she's doing these things, or really wanting to talk to him about it at all. Oh, God.

So not great, but that's why he's come to us. looking for advice on how to finally get his girlfriend to just be honest and tell him what's going on. Yes. Brooke, Croy needs you right now and your wisdom. What do you have to say to Croy? Listen, I am just like you, Croy. I always go to worst case scenario. Like I fall down that rabbit hole of this is going to the most terrible thing ever.

And I think. I was hoping there was some advice off. So that is it. Well, that is the advice. You can only go up from there. You know, like, my mom used to tell me before I'd, like, try out for a team or apply from a job, she'd be like,

you're not going to get that. You probably won't get that. And then when I did, it was so exciting. So maybe I assume she's cheating on you, too. That's good. Yeah. I'm talking to Lexus, Croy. You've already hit rock bottom, Croy.

That must feel good. Yeah, I'm not, I can't say I'm rolling with that advice because I didn't even think about her cheating on me, and now I'm kind of spiraling. Oh, man. Oh, wow. But you're going to spiral up soon. There we go.

It would be better than that. What do you think, Jose? I don't know a ton about women. Shocking. But I'm assuming, if you want one to open up to you, you want to give her, like, food and wine. But you're not with her right now. You're not in the same location. Are you going to get me the food and wine?

No, I'm okay with that. See, the women get excited. So tell her you love her. And then don't talk. Just see what she says. She may feel guilty and open up. She may double down and say, I'll love you forever. Okay.

Okay. Just toss out and I love you and read the vibe from her reaction. What do you think of that, Croy? That's quicker. That's what I should have said. I can figure out a way to weave that in. Yeah, yeah. To say, I love you to your girlfriend of two years. You can figure that out? He's like, when do I say it? It's going to be a tough one.

Somehow I'll figure out a way to drop the album on her, but I think that's actually good advice, Jose. And when she doesn't say anything back to you or says thank you. It's okay, man. Oh, she says thank you. All right, that would have heard. We're running out of time, though, so we just got to start dialing your girlfriend, and Chrissy and see if she answers. Croy, you've got this, man. Okay, I'm ready, guys. Let's do it.

All right, man. I'm a dollar number right now. We'll be waiting quietly to jump in if you need help. Here we go. Hello? Hey, hey, babe, it's me. Babe, where are you calling me from? I'm just calling from another number as all. I wanted to know if I could talk to you real quick for a second.

I'm kind of busy right now. Can we talk to me when I get home? Well, you've been busy like the last three days and I've barely seen you or spoken to you at all. I just need two minutes, okay? Just two minutes, please. Okay. Okay, okay, okay.

So here's the deal. I love you. Okay. That's why you called me? Well, I'm just getting a bad feeling in the pit of my stomach because of the way you've been acting the last month. I don't know what you're talking about. Okay, you gave me that nice watch,

and then you gave it back without asking me. Isn't that a little weird? I mean, I'm sorry about that. I don't know what to tell you. Okay, and then you book us the truth. trip of a lifetime for my birthday and getting excited about it and then text me yesterday saying that you canceled it? I don't know what to say.

Okay, Chrissy, are you about to break up with me? Look, something happened and I don't know how to tell you. Okay, okay, well, listen, I'm here. for you, okay? I love you. Tell me what's going on, please. Well, you know, the watch I got, it was pretty expensive. I mean, maybe you don't know, but it was. Yeah, okay. And the trip I booked was pretty pricey. Okay, well, I didn't ask you to spend that money. You wanted to spend the money. I know, and I thought I could afford it because I was using Apple Pay. Oh, no.

Oh, okay. Did you know that's real money? Like, I just thought it was like Apple points I earned by using my iPhone. Like, I'm stupid. Oh, my God. Hello? Oh, no. Oh, my God.

Hello? Hi. Hi, Chrissy. What? Oh, sweet girl. Yeah, Chrissy. Boy, who? Hello?

Hi, Chrissy. It's my job to tell you right now that you're on a radio show called Brooke and Jeffrey in the and we're doing something called the awkward Tuesday phone call. What? I'm really sorry, Chrissy. I didn't know how else to get you to talk about this. I had to go to the radio to have the radio. That's why I'm calling from a different number because I didn't know what was going on.

Can you just ask me at home? No, everybody knows. It's okay. It's okay. I mean, that's way better than what he thought. Yeah, he should save your relationship. No, it's not. Just like I said, Jeff, it only was up.

No, it's not. I didn't know Apple Pay was using real money because I'm an idiot because I was an Android person for so long. And I just changed over six months ago. Yeah. You connect your credit card to it. I'm sorry, you didn't think Apple Pay was real money. What did you think it was? I thought I was earning like Apple points. It's like taking American dollars from your credit card.

That's why your credit card pops up when you press it. Yeah. You have to link it, right? I just thought that was a deposit. to have just in case. Oh. Okay. To make sure you have an active bank account or something.

It's okay. Adulting's hard and we're not all taught the lessons that we should be taught before being sent out to the real world. Okay. We don't need to condescend to her. I'm not trying to be condescending. I'm trying to make her feel better. Babe, you thought that for using your iPhone for six months, you got enough Apple points to buy a nice watch and a trip to the Bahamas? Well, I use it every day.

I mean, I like her point system better. It would be nice. I just can't believe you put me on the radio. You could have just asked me. Now, everybody knows how stupid I am. No. No. But you just had an airhead moment.

We've all had them before. It's fine. Listen, Dave, this is a lot better than what I thought was happening. I thought you canceled all those things because you were trying to break up with me. Yeah. No, I just didn't know how to tell you because it's like the dumbest thing I've ever done. And I thought you'd think I was really dumb. And now he just put me on blast to the world.

Like, no, don't. He's not trying to put you on blast or do anything. But he did. He only came to us for help because he was trying to ask you about it. And you kept saying, we'll talk later or you're too busy. The good news is this is all finally out in the open. There's solutions. It sounds like you've figured things out about how Apple Pay actually works. What a sweet girlfriend to even plan that stuff to begin with.

She's the best girlfriend ever. I really, really love her, you guys. Oh, with that comment, he just heard himself some boyfriend points there. Yeah, that's right. Fill that bucket, buddy. Which are different than American dollar points just so you know. You can't buy much. Kind of like crypto.

So listen, Chrissy, Croy, both of you, you can go back to planning the 30th birthday, something a little bit more in your budget. But don't be upset with each other. Oh, I'm not upset. I'm not upset at all. This is the best, this is great. The best outcome you've got. Chrissy, how about you?

This is very embarrassing, but I will get over it. Yeah. I mean, Chrissy, look at it this way. A wise old radio host once told me, this is your rock bottom. It can only get better for me. See, Jeff, it works. It actually does work. Thanks, Brooke and Jeffrey in the morning.

Hi, my name is Enya Emanzor. And I'm Drew Phillips. And we run a podcast called Emergency Intercom. If you're a crime junkie and you love. of crimes, we're not the podcast for you. But if you have unmedicated ADHD... Oh my God, perfect. And want to hear people with mental illness, psychobabble.

Yes, yes. Then Emergency Intercom is the podcast for you. Open your free IHeartRadio app. Search Emergency Intercom and listen now. Hi, I'm Janica Lopez and in the new season of the Overcomber podcast, I'm taking you on an exciting journey of self-reflection. Am I ready to enter this new part of my... my life. Like, am I ready to be in a relationship? Am I ready to have kids and to really just

devote myself and my time? I wanted to be successful on my own, not just because of who my mom is. Like, I felt like I needed to be better or work twice as hard as she did. Join me for conversations about healing and growth. Life is freaking hard. And growth doesn't happen in comfort. It happens in motion, even when you're hurting. All from one of my favorite spaces, The Kitchen. Honestly, these are going to come out so freaking amazing. Be a part of my new chapter and listen to the new season of the Overcomber podcast as part of the MyCultura podcast network on the IHeartRadio app, Apple Podcasts, or wherever you get your podcast. There's got to be some people listening to this right now who just had the exact same realization.

That Apple Pay isn't rewards points for using your cell phone. It's actual real American dollars. Some kid is like, I'm about to be in so much trouble. Yep. I'm going to tell you, my kids don't even have phones yet, but I'm still going to go home and show them. Yeah, but it's real money. I mean, Alexis, Starbucks uses this where you can earn Starbucks points

and get free drinks. Why wouldn't Apple do the same exact thing, right? You're right. I don't know. Jeff, get talking to them. I mean, I think our podcast should have a reward system, where for every three awkward Tuesdays you listen to, Brooke will give you $1 straight out of her son's piggy bank.

Hey, I like it. It seems like a good trade. Let's not do that part. Start binging, everyone. Subscribe, like, and earn free money stolen from Brooks' children. I think it's a high-yield piggyback. It's wherever you get your podcast at Brooke and Jeffrey. Hi, my name is Enya Umanzor.

And I'm Drew Phillips. And we run a podcast called Emergency Intercom. If you're a crime junkie and you love crimes, we're not the podcast for you. But if you have unmedicated ADHD, Oh my God, perfect. And want to hear people with mental illness, psychobabble. Yes, yes. Then Emergency Intercom is the podcast for you.

Open your free IHeartRadio app. Search Emergency Intercom and listen now. What would you do if one bad decision forced you to choose between a maximum security prison or the most brutal boot camp designed to be hell on earth? Unfortunately for Mark Lombardo, this was the choice he faced. He said, you are a number, a New York State. number, and we own you. Listen to shock incarceration on the IHeartRadio app, Apple Podcasts, or wherever you get your

podcasts. It's important that we just reassure people that they're not alone, and there is help out there. The Good Stuff podcast, season two, takes a deep look into One Tribe Foundation, a non-profit fighting suicide in the veteran community. September is National Suicide Prevention Month, so join host Jacob and Ashley Schick as they bring you to the front lines of one tribe's mission one tribe save my life twice welcome to season two of the good stuff listen to the good stuff podcast on the iheart radio app apple podcast or wherever you get your podcast do we really need another podcast with a condescending finance brof trying to tell us how to

spend our own money no thank you instead check out brown ambition each week i your host mandy money gives you real talk real advice with a heavy dose of i feel you sis Like on Fridays, when I take your questions for the BAQA. Whether you're trying to invest for your future, navigate a toxic workplace, I got you. Listen to Brown Ambition on the IHeart Radio app, Apple Podcast, or wherever you get your podcast. The Super Secret Festi Club podcast season four is here. And we're locked in. That means more juicy chisement.

Terrible love advice. Evil spells to cast on your ex. No, no, no, no. We're not doing that this season. Oh. Well, this season, we're leveling up. Each episode will feature a special Bestie, and you're not going to want to miss it. My name is Curley.

And I'm Maya. Get in here! Listen to the Super Secret Bestie Club on the IHeartRadio app, Apple Podcasts, or wherever you get your podcast.