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Jeffrey
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Brooke
Are there two sides to every story? Academy Award nominee Robin Wright stars in the girlfriend on Prime September 10, a psychological thriller that will make you question everything. Laura has the perfect life and a son she'd die for, but when he brings home his new girlfriend Cherry, played by Olivia Cooke, something feels off. Also starring Lori Davidson, the Girlfriend is a twisted game of cat and mouse where nothing is what it seems. Don't miss the Girlfriend streaming exclusively on Prime September 10th. Sometimes the truth is just a matter of perspective.
Drew
Hi, my name is Enya Umanzor and.
Jeffrey
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.
Drew
Oh my God, perfect.
Jeffrey
And want to hear people with mental illness psychobabble, yes, yes. Then Emergency Intercom's the podcast for you. Open your free iHeartradio app. Search emergency intercom and listen now.
Announcer
From tips for healthy living to the latest medical breakthroughs, WebMD's Health Discovered podcast keeps you up to date on today's most important health issues. Through in depth conversations with experts from across the healthcare community, WebMD reveals how today's health news will impact your life tomorrow.
Jeffrey
It's not that people don't know that exercise is healthy. It's just that people don't know why it's healthy. And we're struggling to try to help people help themselves and each other.
Announcer
Listen to WebMD Health discovered on the iHeartRadio app or wherever you get your podcasts.
Drew
It's Tuesday, which means it's your Awkward Tuesday podcast. Yep, you're on the second date update. I mean, Awkward Tuesday for us is really kind of like second date in that it's relationship oriented, but it could be any relationship.
Jeffrey
Yeah.
Drew
But today we do have a boyfriend and a girlfriend that are having issues.
Brooke
We do. Which, you know, it's always good when they call a radio station to talk.
Drew
Like, 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.
Brooke
Yes, Libby said, I only listen to you guys in the car, and no, I'm not changing it for anyone.
Drew
Do you think she listens to the podcast or the radio in the car? I don't know.
Brooke
You know, I read it first as.
Drew
Radio and then I'm like, maybe not.
Brooke
Maybe not, maybe not.
Drew
That's so interesting.
Brooke
We are on the radio, just so.
Drew
You guys know that as well. All right. Right, let's get into your podcast. It starts right now.
Jeffrey
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.
Drew
Yay.
Jeffrey
Oh, wait a second.
Drew
Oh, come on, Jeff. You love working with us.
Jeffrey
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.
Drew
Wow.
Jeffrey
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.
Brooke
It's Tuesday.
Croy
It's awkward.
Jeffrey
Tuesday phone call. Do you like it when a significant other makes a big deal about your birthday? Like, goes through the effort to plan things for you, buys you nice presents, does a big surprise?
Drew
Yes.
Jeffrey
I mean, Brooke says she loves it. Unless the surprise is a barbershop quartet.
Drew
That was uncomfy. Okay, that was not cool.
Jeffrey
Okay. But there are contingencies to the surprise, clearly.
Drew
Well, four weird old men standing behind me singing in a radio studio. It's not my idea of a good time.
Jose
Yeah, you know, they're weird.
Jeffrey
Kind of an inside joke. But if you didn't know, a while ago, Brooke's husband and organized that for her on the show, and she absolutely despised it.
Drew
Dude, just making eye contact with people that are singing to you is just too much for me.
Brooke
I wish I was here for that.
Jeffrey
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. Because it sounds like maybe things have changed. Croy, welcome to the show.
Croy
Hey, guys. Thanks for having me.
Drew
Oh, man, I'm sorry. When's your birthday? It's coming up.
Croy
Yeah. Yeah. 30th birthday's coming up in a few.
Jose
Weeks, and you're in the doghouse. Like, you're in trouble.
Drew
That's literally dirty 30. In, like, a fun way. Yeah.
Jeffrey
Okay, so what made you email the show for help about your birthday? Something with you and your girlfriend. What's going on?
Croy
Yeah. Yeah. So my. I've been seeing my girlfriend Chrissy for two years now, and months ago, she started making a big deal about how she wants to go over the top for me for my 30th birthday.
Jose
That's awesome.
Brooke
That's a great girlfriend.
Jeffrey
Yeah. What does that mean, though?
Croy
Well, it means that she got me an early birthday present, which was a really nice watch.
Drew
Oh.
Croy
And in addition to that, for the actual birthday, she booked us a trip to the Bahamas.
Drew
Wow, that's insanity.
Jeffrey
You didn't take the watch as, like, kind of an insulting present, though.
Drew
Wait, what do you mean? Like, you're running out of time. You're in 30.
Jeffrey
Like. Yeah. Never on time for stuff.
Drew
On time.
Jeffrey
I thought, now you're getting old times running out. You didn't read into it like that?
Jose
Symbolic.
Croy
No. Maybe if it wasn't as nice a watch as this, but, I mean, I didn't even think about that Rolex.
Jose
Are you calling me old?
Drew
Wait, are you calling. And there's a. Like, you have an upcoming Bahamas trip, right?
Croy
Well, yeah, but I mean, even more than that. It's not just the watch. In 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.
Drew
So, wait, where does the problem come in?
Croy
So the problem comes in that last week she tells me that she had to return my watch.
Drew
What?
Jeffrey
Wait, what?
Drew
Oh.
Croy
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.
Drew
Uh, oh.
Croy
And I was like, what does that mean? And she was like, I don't really want to talk about it.
Drew
Oh, bummer. I immediately think maybe she overspent. Yeah. Yeah. You know, like, is. 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.
Jose
And we could do without the watch, but we'll still do the vacation.
Drew
Yeah. Yeah.
Croy
Well, my thoughts are worse because after that happened last week, she texted me yesterday saying that she had to cancel the trip.
Drew
What?
Croy
No.
Jeffrey
Now Bahamas are off the table, too?
Croy
Yes.
Jeffrey
What are you thinking?
Croy
I. I think she's planning to break up with me.
Jeffrey
Oh, really? Come on, stand up for. No, she's not planning to break up with you. You're a good guy.
Brooke
Out the breakup, though. Why wouldn't she?
Drew
Just because she wants to get the refund first. Maybe she doesn't want to spend the money. I don't know. But I would feel the same. Because why? Why else would you do that?
Jose
Yeah, like, why can't you just rebook? You can't do Cleveland instead of, like, the Bahamas.
Croy
It.
Jeffrey
Sure. Even if it is too expensive, you can find a more affordable.
Drew
I think, more than anything. Why? No explanation. Why isn't she telling you? Have you asked her what's going on?
Croy
When I kept asking her why, she was like, oh, no, we'll do a different thing. We'll do a different thing 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 gonna break up with me, and I don't know why. I have no idea why.
Drew
Oh, man, that's tough. Like, I think I'd be pissed. 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.
Brooke
Better be taking it back to plan something.
Drew
Better take away presents that have already been gifted.
Jeffrey
Is that your suggestion to him right now? He should dump her first before she dumps him?
Drew
No. No, no, no. Well, maybe depending on what she has.
Chrissy
So.
Croy
I'm not that shallow. And really, I'm just more concerned about our relationship here.
Drew
No, that's good. That's good. You seem like a really good guy.
Jeffrey
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.
Croy
Yeah, none that I can think of.
Drew
Okay, that's good.
Jeffrey
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.
Croy
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.
Jose
We could just call a bunch of, like, Chuck E. Cheese's and see if there's any bookings.
Drew
You think she could still be planning a surprise?
Jose
There's gotta be a surprise from the surprise. I don't know.
Croy
It seems like the birthday is, like, far away in her mind, too. Like. Like she's not even planning anything anymore, you know?
Jeffrey
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.
Croy
That's intense.
Jeffrey
We'll try to get you some answers in your awkward Tuesday phone call.
Croy
Thank you, guys.
Jeffrey
Next. It's awkward.
Drew
It's Tuesday.
Jeffrey
It's awkward Tuesday phone call. What are the subtle red flags from a significant other that show they're attempting to break up with you?
Drew
You.
Jose
Oh, man.
Jeffrey
Maybe if they change your Netflix profile name to just the word guest.
Drew
Oh, ouch. Why did that hurt?
Jeffrey
That's not a good sign.
Jose
Crying in the opening screen.
Brooke
You're still on the profile.
Jose
You still have access.
Jeffrey
Or if you find a PowerPoint presentation on their computer about why you should start seeing other people.
Jose
Oh, that is very specific.
Jeffrey
It's a red flag, but not saying it's totally over yet.
Jose
Whose is this?
Drew
Could have helpful information in it.
Croy
That's true, too.
Jeffrey
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. 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 to help him out?
Drew
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.
Jeffrey
Was some advice on it.
Brooke
So that is.
Drew
Well, that is the advice. You can only go up from there. You know, like. Like my mom used to tell me before I'd, like, try out for a team or apply for a job. She'd be like, you're not gonna get that. You probably won'.
Chrissy
That.
Announcer
And then when I did, it was so exciting.
Brooke
So maybe assume she's cheating on you, too.
Jeffrey
That's good.
Drew
Yeah. We're talking Alexis.
Jeffrey
You've already hit rock bottom, Croy. That must feel good.
Croy
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.
Jeffrey
Oh, man. Oh, wow.
Drew
But you're going to spiral up soon.
Jeffrey
There we go.
Drew
Better than that.
Jeffrey
What do you think, Jose?
Jose
I don't know a ton about women. Shocking. Okay, 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.
Drew
Are you gonna give me the food and wine?
Jeffrey
She perked up.
Jose
Tell her you love her.
Drew
Oh.
Jose
And then don't talk. Just see what she says. She may feel guilty and open up. She may double down and say, I love you forever.
Drew
Okay.
Jeffrey
Okay. Just toss out and I love you and read the vibe from her reaction. What do you think of that?
Jose
Quicker.
Croy
That's what I should have said. I can figure out a way to weave that in. Yeah. Yeah.
Brooke
Say I love you to your girlfriend of two years.
Jeffrey
Yeah.
Drew
Figure that out.
Jose
He's like, what do I say?
Jeffrey
It's gonna be a tough one. Somehow I'll figure out a way to drop the L bomb on her. But I think that's actually good advice, Jose.
Drew
And when she doesn't say anything back to you or says thank you, it's okay, man.
Jeffrey
We're running out of time, though, so we just gotta start dialing your girlfriend Chrissy and see if she answers. Kroy, you've got this, man.
Croy
Okay, I'm ready, guys. Let's do it.
Jeffrey
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.
Chrissy
Hello?
Croy
Hey, hey, babe, it's me.
Chrissy
Babe, where are you calling me from?
Croy
I'm just. I'm just calling from another number. Result. I wanted to know if I could talk to you real quick for a second.
Chrissy
I'm kind of busy right now. Can we talk anyway when I get home?
Croy
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.
Chrissy
Okay.
Croy
Okay, okay, okay. So here's the deal. I love you.
Chrissy
Okay? That's why you called me?
Croy
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.
Chrissy
I don't know what you're talking about.
Croy
Okay? You gave me that nice watch and then you gave it back without asking me. Isn't that a little weird?
Chrissy
I mean, I'm sorry about that. I don't know what to tell you.
Croy
Okay, and then you book us the trip of a lifetime for my birthday and get me excited about it and then text me yesterday saying that you canceled it.
Chrissy
I don't know what to say.
Croy
Okay? Chrissy, are you about to break up with me?
Chrissy
Look, something happened and I don't know how to tell you.
Croy
Okay? Okay, well, listen, I'm here for you, okay? I love you. Tell me what's going on, please.
Chrissy
Well, you know, the watch I got you was pretty expensive. I mean, maybe you don't know, but it was. Yeah, okay, and the trip I booked was pretty pricey.
Croy
Okay, well, I didn't ask you to spend that money. You wanted to spend the money.
Chrissy
I know, and I thought I could afford it because I was using Apple Pay.
Drew
Oh, no.
Croy
Okay.
Chrissy
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.
Drew
Oh, my God. Hello?
Jeffrey
Oh, my God.
Drew
Hello?
Jeffrey
Hi. Hi. Chrissy.
Drew
Laughing politely what? Oh, sweet girl.
Jeffrey
Yeah. Chrissy.
Chrissy
Hello.
Drew
Hi.
Jeffrey
It's my job to tell you right now that you're on a radio show called Brooke and Jeffrey in the Morning and we're doing something called the Awkward Tuesday Phone Call.
Chrissy
What?
Croy
I'm really sorry, Chrissy. I didn't know. I didn't know how else to get you to talk about this. I had to go to the radio to have a radio. That's why I'm calling from a different number, because I didn't know what was going on.
Chrissy
Just ask me at home.
Drew
No, no, it's okay. It's okay. I mean, that's way better than what he thought. Yeah, he said. No, it's not. Just like I said, Jeff, it only was up.
Croy
No, it's not.
Chrissy
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.
Drew
Yeah. You connect your credit card to it.
Jeffrey
I'm sorry, you. You didn't think Apple Pay was real money? What did you think it was?
Chrissy
I thought I was earning, like, Apple points, but it's like taking American dollars from your credit card.
Brooke
Yeah, that's why your credit card pops up when you press it.
Jeffrey
You have to link it.
Croy
Right.
Chrissy
I just thought that was a deposit to have just in case, to make.
Jose
Sure you have an active bank account.
Drew
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.
Jeffrey
Okay? We don't need to condescend to her.
Drew
I'm not trying to be condescending. I'm trying to make her feel better.
Croy
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?
Chrissy
Well, I use it every day.
Drew
I mean, I like her point system better.
Chrissy
I just can't believe you put me on the radio. You could have just asked me. Now everybody knows how stupid I am.
Drew
No, no, you just had an Airhead moment. We've all had him before. It's fine.
Croy
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.
Chrissy
Yeah, no, I just didn't know how to tell you because it's, like, the dumbest thing I've ever done, and you think I was really dumb, and now you just put me on blast to the world, like.
Jeffrey
Yeah, well, he's not trying to put you on blast or do anything. He only came to 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.
Drew
And what a sweet girlfriend to even play on that stuff to begin with.
Croy
She's the best girlfriend ever. I really, really love her.
Jeffrey
You guys with that comment. He just earned himself some boyfriend points. Points there.
Croy
Yeah, that's right.
Drew
Fill that bucket, buddy.
Jeffrey
Which are different than American dollar points. So you know you can't buy much.
Jose
Kind of like crypto.
Jeffrey
Yeah. 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.
Croy
Oh, I'm not upset. I'm not upset at all. I. This is the best. This is great.
Jose
The best outcome got.
Jeffrey
Chrissy, how about you?
Chrissy
This is very embarrassing, but I will get over it.
Jeffrey
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 from there.
Drew
See, Jeff, it works.
Jeffrey
It actually does work.
Drew
Thanks.
Announcer
Brooke and Jeffrey in the morning Are.
Brooke
There two sides to every story? Academy Award nominee Robin Wright stars in the girlfriend on prime September 10. A spine tingling psychological thriller that will make you question everything you think you know. Laur has the dream job, the perfect husband, and a son she'd die for. But when her beloved Daniel brings home his new girlfriend, Cherry, played by Olivia Cook, something feels off. Is Cherry the sweet, innocent girl she appears to be? Or is there something more manipulative beneath the surface? And how far will a mother go to protect her son? Also starring Lori Davidson, the Girlfriend is a twisted game of cat and mouse where nothing is what it seems and everyone has something to hide. Don't miss the Girlfriend. Streaming exclusively on Prime, September 10th. Sometimes the truth is just a matter of perspective.
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Jeffrey
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.
Jose
Some kid is like, I'm about to be in so much trouble.
Drew
Yep, I'm gonna tell you, my kids don't even have phones yet, but I'm still gonna go home and show them.
Jeffrey
Yeah, it's real money. I mean, Alexis Starbucks uses this where you can earn Starbucks points and earn and get free drinks. Why wouldn't Apple do the same exact thing? Right?
Brooke
You're right.
Chrissy
I don't know.
Drew
Jeff, get talking to them.
Jeffrey
I mean, I think our podcast should have a reward system where for every three awkward Tuesdays you listen to. Okay, Brooke will give you $1 straight out of her son's piggy bank.
Jose
Hey, seems like a good trade.
Drew
Let's not do that part.
Brooke
Start binging everyone.
Jeffrey
And earn free money stolen from Brooks children.
Jose
I think it's a high yield piggy bank.
Jeffrey
It's wherever you get your podcasts.
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Jeffrey
It's football season and now you can get anything you need for game day delivered with Uber Eats. Well, almost almost anything. You can't get a running back, but baby back ribs. Yes, Uber Eats official on demand food delivery Partner of the NFL with depression.
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FX Lowdown Narrator
This episode is supported by FX is the Lowdown starring Ethan Hawke. Allow us to introduce you to Lee Raybon, a quirky journalist, rare bookstore owner slash unofficial truth seeker who is always on the tail of his latest conspiracy. This time, his most recent expose puts him head to head with a powerful family that rules Tulsa, meaning only one he must be onto something big. FX is the Lowdown premieres September 23rd on FX stream on Hulu.
Jeffrey
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Episode: Awkward Tuesday: Unhappy Birthday
Date: September 9, 2025
Host: iHeartPodcasts
This episode of "Brooke and Jeffrey: Second Date Update," specifically the "Awkward Tuesday" segment titled "Unhappy Birthday," focuses on a relationship dilemma involving listener Croy and his girlfriend Chrissy. Croy reaches out to the show after his girlfriend unexpectedly cancels elaborate birthday plans without explanation—leading him to fear an imminent breakup. The hosts attempt to uncover the real reason behind Chrissy’s actions and facilitate a frank conversation between the couple, culminating in a funny and revealing twist.
"I think she's planning to break up with me."
— Croy, [08:40]
"Man, that's tough. I'd be pissed...if my boyfriend gave me these big grandiose things and then took them away, I'd be like, what the hell?"
— Drew, [09:35]
[14:42-17:16] The group calls Chrissy, with Croy nervously leading the conversation.
[15:15] Croy tries a direct approach:
"I love you."
— Croy
[16:14] Chrissy finally opens up:
"Look, something happened and I don't know how to tell you."
— Chrissy
[16:53] The twist: Chrissy admits she misunderstood Apple Pay, thinking it was "Apple points" earned just by using her phone, not real money. She’d spent beyond her means, realizing only when the bills hit.
"Did you know that's real money? Like, I just thought it was like Apple points I earned by using my iPhone."
— Chrissy, [16:53]
[19:06] Croy is fully supportive and relieved:
"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."
— Croy
[19:43] Hosts encourage the couple to plan something more budget-friendly, pointing out how sweet Chrissy’s intentions were.
[20:33] Jeffrey delivers a closing line:
"A wise old radio host once told me, this is your rock bottom. It can only get better from there."
The episode is a classic Brooke & Jeffrey mix of playful banter, gentle ribbing, genuine advice, and unexpected humor. The awkwardness is handled with warmth and good spirits, and the final reveal is both funny and relatable—a "millennial moment" involving tech confusion rather than relationship doom.
Best Notable Quotes:
"Did you know that's real money? Like, I just thought it was like Apple points I earned by using my iPhone."
— Chrissy, [16:53]
"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?"
— Croy, [18:37]
“A wise old radio host once told me, this is your rock bottom. It can only get better from there.”
— Jeffrey, [20:33]
If you missed this episode, you'll catch all the feels: confusion, concern, relief, and lots of laughter about the everyday misunderstandings that can come between couples. In classic Brooke & Jeffrey style, the mystery isn’t a breakup—but a funny, innocent mistake, resolved on-air with empathy and humor.