Brooke and Jeffrey: Second Date Update - Awkward Tuesday: Lyndsey On My Leg

Episode Date: March 24, 2026

Lyndsey heard what romantic gesture her boyfriend of 4 months was trying to pull off for her and she is ADAMANT that we help her STOP HIM at ALL COSTS! See omnystudio.com/listener for privacy information.

Getting ready for a game means being ready for anything. Like packing a spare stick. I like to be prepared. That's why I remember, 988, Canada's suicide crisis helpline. It's good to know, just in case. Anyone can call or text for free confidential support from a train responder anytime. 988 suicide crisis helpline is funded by the government in Canada. I became a millionaire overnight and lost everything that actually mattered.

Hold on, Sophia. Did you just say they lost everything after becoming a millionaire? That's right. And it gets worse. It's inheriting too much drama week on the OK Storytime podcast, so we'll find out soon. This person writes, I just inherited a fortune after losing my mom. And now my girlfriend's entire family is coming out of nowhere with her hands out. And my girlfriend is already giving my money away.

So the girl he wants to marry is already sending money out the door. Find out how it ends. Listen to the OK Storytime podcast on the Iheart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Bailey Taylor, and this is it girl. This podcast is all about going deeper with the women's shaping culture right now. Yes, we will talk about the style and the success, but we are also talking about the pressure, the expectations, and the real work behind it all. As a woman in the industry, you're always underestimated.

So you have to work extra hard in a way that doesn't compromise who you are in your integrity. You know, I like to say I was kind of like a silent ninja. Listen to It Girl with Bailey Taylor on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. You know Roll Doll. He thought up Willie Wonka and the BFG. But did you know he was a spy? In the new podcast, The Secret World of Roll Doll, I'll tell you that story, and much, much more. What?

You probably won't believe it either. Was this before he wrote his stories? It must have been. Okay, I don't think that's true. I'm telling you. I was a spy. Listen to The Secret World of Roll Doll on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. March Madness is here, and if you're trying to keep up with everything happening on and off the court,

we've got you covered on the podcast, Flaigrant and Funny. Do you want to start with the first special for the Big Ten coach of the year? Oh, whatever. Would you like to? So you're a Spartan, is that what I'm getting? On Flagrant and Funny, we're giving our unfiltered takes on the biggest moments of the conversations everyone's having. So whether your bracket is busted or you just want the latest on the tournament, we got you. Listen to Flakron and Funny with Kerry Champion and Jamel Hill on the IHeart Radio app,

Apple Podcasts, or wherever you get your podcast. presented by Capital One, founding partner of IHart Women's Sports. All right, here it is a brand new episode for you. Thank you so much for being on our second date podcast. We love that you're here. We're glad you found us. It's looking for the morning, especially the official site, you know? Yeah, totally.

Instead of the, you know, other stuff. Yeah, and a lot of you find those first, but then you make your way to us. And for that we love you. Yes, thank you for finishing my thought. It was almost complete Alexis. All right, before we get to the new awkward Tuesday, what is the comment that you want to read? Yeah, Charlie's testes said, I'm traveling solo around Europe for three months and have been listening to your podcast in every country I visit. I now associate your episodes with places I've been.

That's wild to think about it. That's so cool. He's like, oh, I remember the leaning tower of Pisa. That's when Jacqueline broke up with Bobby. You got to respond back. What's the coolest place you've ever laughed at us? Oh, I like that. I like that.

That's so cool. We'll have a good safe trip and we're all slightly jealous. Yeah, let us know where today is for you. And give us some hot travel tips. We're always about that. All right, let's get you a brand new Awkward Tuesday right now. Alexis, what's the most romantic thing a guy has ever done for you? Oh, no, don't make her throw up, dude.

Like a rose pedal path to like a hot tub, probably. Whoa. And we ended things. Yep. That was your reaction? You broke it off? Not immediately. Oh, okay.

She accepted it and then the next day. to his song, hey there, Delilah, but hey there, Alexis. That one was bad too. Every guy did that. Yeah. You didn't like any of it. No, same guy. Well, apparently you and our listener on the phone today are very, very similar.

Because when her boyfriend of four months told her the gesture that he'd been planning, her immediate response was to try and stop him from doing it at all costs. And that's where we come in. Can we help convince this Romeo to tone it down without fully crushing his romantic spirit? We're going to try in your brand new Awkward Tuesday phone call. Next. It's awkward. It's Tuesday.

It's awkward Tuesday phone call. Some people in relationships enjoy grand romantic gestures. Yeah. Like surprise getaways. Sending dozens of roses. I miss sending flowers. creating a life-sized wax sculpture of your girlfriend. Oh my gosh.

Then lighting it on fire. Because it's actually a giant scented candle. Oh. Uh-oh. Don't hit the ah button. That's sweet. Just you and her and your house full of cranberry cinnamon. Oh, that's better than burning hair.

Ew. But you know what? Stop the music real quick. What? Because not everybody wants that stuff. Like our listener, Lindsay, who's asking for our help today to tell her. her boyfriend, chill out with the romance, bro. Oh, yeah.

Lindsay, why do you insist on pushing love away? Hi. Yeah, she's like, I don't know how to respond to that. A hello is nice to start a convo. That's really funny, Lindsay. Hi, Lindsay. So tell us what's going on with you and your boyfriend. What's his deal?

So I've been dating Andre for about four months. Oh, it's a new relationship. I see. That's the best part, too. It's exciting. Clearly not for her. Yeah. Well, I mean, listen, he's very sweet.

He's romantic. Like, he is a great guy, but, like, it's only been four months. You know, it's still very early. Yeah. Okay. The other day he came up to me with this idea that he wants to get a tattoo of my name on his leg. Okay. On his leg?

Not. Can we go back to the couple dozen of flowers? That's better. I mean, you could be together for 20 years and still, that's a sketchy ass. Why? Why would he want to put Lindsay? on his leg. Okay, so this is also a red flag.

He says he wants other women to know that they can't have him. He's mine, which is, you know, nice. But they only know if he's wearing shorts. Yeah. So that's probably bad. It could be on the kneecap, Brooke. How do you see it underpants?

With a hole in your jeans. I see. I see. There's a zipper right there. Okay. So this is his way of deterring other women. Because he's obviously so desired. God.

But you're going to get a kick out of this one, though, because he wants to cover up an old tattoo of a different girlfriend's name. Oh, no. This is his thing. Well, that's good. You don't want another girlfriend's name. Wait, but the first girlfriend's name didn't deter you. I didn't know about that until a week ago. Ah, yeah.

Remain. Eye contact, everything above the belt. He is smart. If you have another girl's name on your leg, you should probably not tell a woman until two, three years into the relationship. As long as you can hold out, I guess. How does this man not learn his mistake? Right? He's already made the mistake once, and now he wants to do it again, essentially.

Right. That's exactly what I'm saying, but now he's already made an appointment, and I need to have a serious conversation with him about this. Okay. The appointment's been made? Yeah. That's crazy. So you're not into the idea.

Like, what is giving you so much hesitation about it, like specifically? Well, one, it's way too early in the relationship. It's been four months. And I don't think that matters to him. I think he likes to move quickly. I think it'll make things really awkward and put way more pressure on a relationship. It already is putting pressure on the relationship. Yeah.

And there's like an obligation to stay together because your name's tapped to me. Oh, yeah. Has he said I love you yet? No. Okay, that's good. He shouldn't have. But you would think that word would be said before. He doesn't have to say, I love you when he can write it on his leg with heart.

You haven't even said the elves and your name around. You're getting tattoos. Have you? So it's wild that you haven't said, no, that's not a good idea to me. Why? Why haven't you just told him that? Outright. I just, I don't want to crush him because he is a sensitive guy and this is a big deal for him.

But he's already made this mistake once before. I don't want to be another mistake. I mean, I can understand that's the tough part because when somebody goes all out for you and puts their entire heart into something and you come at them like, ew, or that's weird or that's gross. Like that could totally crush something. It's not gross. It's just a terrible decision that he's already made once and obviously regretted. So why would she let him do it again?

Exactly. Those words would absolutely destroy him if you said it to his face. Maybe he needs to hear that. Like sometimes the hard truth is just what has to happen. He thinks it's for her, but she doesn't want it at all. Yes. I think he's romanticizing it in his head. It's just so hard to call it romantic when it's over the top of another woman's day. Yeah.

So we haven't given our advice yet, but it sounds like, Like, from the temperature in the room, it's going to be pretty harsh. I mean, we can cover it in other ways. There's tons of ways they cover bad tattoos. But that's not the romantic way that he wants to do it. How do you, like, deliver that message to him in a gentle way? Yeah. That doesn't crush him.

That's what I'm trying to figure out right now. I mean, calmly, gently. Like, Brooke, imagine if Jeff got your name tattooed in his arm without asking you. We just have to cut the arm off. I mean, that would be the only solution. I mean, that would be extra weird because Brooke and I aren't like romantically together or anything like that. I want to get the show logo tat in. Yeah, I don't want to do that.

It'd be a weird romantic gesture for someone you're not dating. That's not romantic, guys, we work together. I just think tattoos should be like a selfish thing. Like, whatever you want. Not for someone else. Got it. Yeah, I agree too. Okay, so with that being said, Andre wants to do this maybe just for himself.

Oh, so he'll always remember her. Yeah, to prove to himself, how. much he loves her. This is his own challenge. It's hard to spin the light on this. Like how much you love the last girl. Yeah. I'm just curious, what was the last girl's name? Oh, yeah. Tiffany.

Oh, in the same length. It makes sense. Yeah, that's good. And they both end with why. So there's that and they'll have to cover up. Yeah, I'll be easier for him, but we're going to try to convince him to not go through with that when we come back, give you our advice and let you make your awkward Tuesday phone call to your boyfriend to convince him not to get a tattoo of your name on his leg. Yeah. To cover up his ex's name.

Yeah. We're going to skip that part. It's important. We'll do it right after this. Hold on. It's awkward. It's Tuesday. It's awkward Tuesday phone call.

You've heard of the five love languages. Tattooing people's names should be the sixth. No, no. Because that's what our listener, Lindsay, is dealing with. She has a very romantic-minded boyfriend named Andre, who, after four months together, has told her, I've made an appointment to get a tattoo of your name on my leg so

that you know I'm 100% yours. Yeah, okay. And it's also covering up the exes name. Yeah. It's a good point to bring up. So Lindsay thinks it's a little bit too soon to be doing this. But regardless, she needs our help on how to tell him gently

that maybe this isn't the right time for something like that. And perhaps we can convince him to just think about it, or at least cancel his appointment. Okay. So I'm interested to hear what my co-host have to say, Brooke, how would you crush a man's dreams?

This may be shocking to you, Lindsay, but I think you tell him, do it. Oh. Dare him. And then you follow it up with, but do you know what would be even more meaningful than my name is something that we love together, like a symbol. Or maybe you both love burritos. or you love pickles. I'm thinking long and thin.

A big tree with a lot of leaves. What do you think about getting a caserito tattooed on both of your legs? I like it. I'm not willing to get a tattoo. No, I'm not telling you to. I'm just telling him to choose one out of something that you both like so that when you break up, it's something he still likes. Excuse me.

Not when they break up, Brooke. They're going to be together forever. Yeah, Brooke. How dare you? It's not the vibe. I'm getting. No. I love that idea. That's good. Lindsay, you still like him. You want to stay with him. You just don't want him to get the name

tattooed. So, Jose, what's your advice? I believe there's a compromise here that we start with just one letter. Every year. Right? Every year, one letter. Maybe you start with an L. Okay, so he'll be Liffany for a while because it's covering up the exes' name Tiffany. He will be Lee for a couple years. But listen, that way if you guys continue to date, you can add a letter each year. Interesting. And it's like a tradition.

Lindsay, what do you think? That's cute. I think that that's a big idea. And it's just like a tally. Then it's not a crazy tattoo. We'll have a big L tattooed on him at first. And the second year is I, which is also the start of his ex's name, second letter. So that's good.

Yeah, that's good. It seems to be a year. Oh, yeah. So you only need to block out a few letters now. Yeah. It's like, I mean, that's the best advice that we've had all year. Wow, thanks. I'm honored.

It's a very low bar that we'd set for ourselves. but that's what we've got for you, Lindsay. You can do what you want with it, but I'm going to dial your boyfriend's number right now and let you make your awkward Tuesday phone call. Are you ready? Yes, I'm ready. Hello?

It's me. How are you doing? How's your day? Where are you calling you from? Just this different number. I had to borrow someone to go on my phone died. It's fine. I'm curious how your day is going.

What's up? Good. Get my day going, getting things out. I took out the garbage. So that's out there where you go. You know, it's going all right. How's going to go, then? Other than your phone dying, obviously.

I know. I need to bring a charger with me everywhere I go. But I wanted to discuss something with you real quick. Do you have time? Yeah. I can take a break from taking out of the trash for good, yes. Okay, thank you. So this tattoo.

idea that you brought up to me the other day. I don't wait to get Tiffany's name off me. Yeah, and I can't wait for you to stop saying her name too. But I think maybe we could do something a little more meaningful than my name, and maybe you could get something like that we both love together, like chips in caseo crosses my mind or how we both love Neopolitan-style pizza. I think that could be a cute tattoo that could definitely cover up

her name. What's the deal? Are you even drugs or something to say? What's up? What? Why would you even say that? No. It's cute and all, but it's like, I want your name on it so that

everyone else knows I'm taken. I don't want them to think I'm taken by chips and queso. I understand that, but I think the biggest reason why I'm bringing this up is that you don't even know if you love me yet. So tattooing my name on your body just seems like a really big

jump, you know what I mean? Babe, you don't know if I love you or not? Are you serious? Well, I mean, you haven't said it, so how would I know? I mean, I'll say it right now on the file. I love you. Like, it's been four months. Some people just know, you know? It's just

sorry, like I thought with all the, with everything that are showing you and done and putting you know, wanted to tap to your name. I felt like it was almost implied, but yeah, I love you. Oh, my God. Okay. I, this is how you're going to say,

I love you for the first time. We've been dating for four months. I think that four months is a little too soon to be exclaiming love for each other, don't you? Yeah, but some people just know, and, I mean, four months, some people just know in less time than that, you know? Like, do you have that feeling?

Like, you don't, you don't feel, the same way? Well, of course I feel that way, yeah, but I'm just trying to wrap my head around it. All right, well, what if, you know, what if you wrap your head around this? What if you were my wife? Oh, what? What? What?

What did you just say? Okay. I, all right, let's just be blunt about it. Lindsay, who you married me? Oh, stop it. We should have hit the button so much earlier. We was waiting for the answer from Lindsay. I think we know it.

Did he pass out, Andre? Hello. What's going on? Who's this? Hey, Andre, this is a radio show that you're on right now called Brooke and Jeffrey in the morning. We have never heard so much done in one small conversation. So we're on the radio right now. Does that make it more romantic?

Oh. I mean, had I known I would have planned better, but... Or planned it all, my friend. Yeah. I mean, yeah, you guys call me off garb, whatever. Like I said it before, when you know, you know. And some people just know when it's time, like that... Okay.

You are a spontaneous man. Yeah, I don't know how Lindsay's feeling about this right now. Lindsay, you're still there? Yeah, I'm still here. Oh, God. That's here at me first. That was a long pause. Yeah, it was.

Okay, so there was a lot said there in the last few minutes. You should probably just talk to Andre about the feelings and the questions that are all coming out at once. I don't even know if we did dress the tattoo. Yeah, I think that's a good idea, too. Go ahead. Now would be the time. I mean, yeah, I didn't really necessarily hear an answer. So the question still stands.

I have to say no. chips and queso. That's what you're saying no to, Lindsay. Just say no to every question, Jeff. I think it's moving way too fast, and it's starting to freak me out a bit. And as much as I adore you,

I don't want to be just another name tattooed on your body that you're trying to cover up in a year. Oh, okay, so I think I get it. It's not necessarily like a no, it's more like a not yet. I think that's a positive spin. Yes.

You can look at it that way. Yeah. Okay. To all the questions that have been posed today, not yet. The tattoo. Yep. The wedding. The L word.

Any other big moves you were thinking of making right now, Andre? Well, we probably don't even want to go there. Andre, why are you trying to fast forward everything? I know, it's not like a garbage that you're taking out really quickly. You want to take your time and enjoy it. Dave, I feel like these guys are trying to tell us how to live our romantic life. He's not wrong. We are.

We're trying to help, though. Truly, Lindsay came to us seeking advice on how to have this conversation with you because as much as she really enjoys your relationship and likes you, Andre, a lot of these steps are happening too quickly for her speed. Yeah, absolutely. Okay. Are you hearing her, Andre? I guess I'm more on the way.

If it's what's going to lead to, then I'll be as patient as anything. Yeah, it's like you listen to us. How about tonight at home? You get some nacho-caso dip and some Neapolitan pizza, and you see what words come out of her mouth there. But in the meantime, what am I supposed to do with this Tiffany tattoo? Oh, good question. Probably stop mentioning her, is the first thing. Maybe just do a big black box on that one.

Just wear pants, man. All right, we'll figure something else on the cover of them. Oh, look at that. What an understanding guy. I hope you share pictures of it with us. Yeah, we love to see it. We'll definitely send pictures. Joe, Jess and the dad, too.

Yeah. Yeah. Okay. Brooke and Jeffrey in the morning. Getting ready for a game means being ready for anything. Like packing a spare stick. I like to be prepared. That's why I remember 988, Canada's suicide crisis helpline.

It's good to know, just in case. Anyone can call or text for free confidential support from a train responder. Anytime. 988, suicide crisis helpline is funded by the government in Canada. You know Roll Doll, the writer who thought up Willie Wonka, Matilda, and the BFG. But did you know he was also a spy? Was this before he wrote his stories? It must have been.

Our new podcast series, The Secret World of Roll Doll, is a wild journey through the hidden chapters of his extraordinary, controversial life. His job was literally to seduce the wives of powerful Americans. What? And he was really good at it. You probably won't believe it either. Okay, I don't think that's true. I'm telling you. I was a spy.

Did you know Dahl got cozy with the Roosevelt's? Played poker with Harry Truman and had a long affair with a congresswoman. And then he took his talents to Hollywood, where he worked alongside Walt Disney and Alfred Hitchcock, before writing a hit James Bond film. How did this secret agent wind up as the most successful children's author ever? And what darkness from his covert past seeped into the stories we read as kids.

The true story is stranger than anything he ever wrote. Listen to the secret world of Roll Dahl on the IHeart Radio app, Apple Podcast. wherever you get your podcast. That call definitely lived up to the billing. It was certainly awkward. But you know what's going to be really awkward is if we check in in a few months

and Andre's back together with Tiffany because he couldn't get her name off of his leg. I didn't even think about that possibility. Oh, no. Maybe you just felt like it was fake at that point. Or you only date Tiffany's. Yes. Another Tiffany's.

There are a lot of options out there. Sorry, Lindsay, if you're listening to it. Sorry, Lindsay, but we did achieve a lot. We got Andre to cancel his upcoming tattoo appointment. Did you confirm that? Are we sure? It seemed like he was definitely backing off. We helped shut down his marriage proposal.

And we made him question whether his girlfriend even loves him at all. Good work, team. Yeah. And we could do the same wonders on your blossoming relationship. If you email the show, we'll help you call whoever you need, give you a little advice and help you settle all the problems that are going on in your personal life. All of them, huh? All of them. Just with one phone call.

At least one's involving tattoos. Okay. We'll save that. Go find us online if you want to see our podcasts. They're available wherever you get them at Brooke and Jeffery. I became a millionaire overnight and lost everything that actually mattered. Hold on, Sophia. Did you just say they lost everything after becoming a millionaire?

That's right. And it gets worse. It's inheriting too much drama week on the OK Storytime podcast, so we'll find out soon. This person writes, I just inherited a fortune after losing my mom. And now my girlfriend's entire family is coming out of nowhere with her hands. hands out and my girlfriend is already giving my money away. So the girl he wants to marry is already sending money out the door.

Find out how it ends. Listen to the OK Storytime podcast on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts. I'm Bailey Taylor and this is It Girl. This podcast is all about going deeper with the women's shaping culture right now. Yes, we will talk about the style and the success, but we are also talking about the pressure, the expectations, and the real work behind it all. As a woman in the industry, you're always underestimated.

So you have to work extra hard in a way that doesn't compromise who you are in your integrity. You know, I like to say I was kind of like a silent ninja. Listen to It Girl with Bailey Taylor on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts. You know Roll Doll. He thought up Willie Wonka and the BFG. But did you know he was a spy? In the new podcast, The Secret World of Roll Doll, I'll tell you that story. and much, much more.

What? You probably won't believe it either. Was this before he wrote his stories? It must have been. Okay, I don't think that's true. I'm telling you. I was a spy. Listen to the secret world of Roll Dahl

on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Marsh Madness is here, and if you're trying to keep up with everything happening on and off the court, we've got you covered on the podcast, flagrant and funny. You want to start with the first question

for the Big Ten Coach of the year? Oh, whatever. Would you like to? So you're a Spartan, is that what I'm getting? On Flakron and Funny, we're giving our unfiltered takes on the biggest moments the conversations everyone's having. So whether your bracket is busted or you just want the latest on the tournament, we got you.

Listen to Flacrid and Funny with Kerry Champion and Jamel Hill on the IHeart Radio app, Apple Podcasts or wherever you get your podcast. Presented by Capital One, founding partner of IHart Women's Sports. Good people. What's up? What's up? It's Questlove. So recently I had the incredible opportunity to have a real conversation with

with an actress and producer, Jamie Lee Curtis, from routines to recovery, true lies, and a certain Jermaine Jackson music video. Jamie's surreal and raw, and something I really admire about her. I am so happy that I'm the head bitch in charge at 67, that I have the perspective that I have at my age, to really be able to put all of this into context.

Listen to the Questlove show on the I-Heart, radio app, Apple Podcasts, or wherever you get your podcasts.