Brooke and Jeffrey: Second Date Update - Awkward Tuesday: From Ferrari To Friendzone

Episode Date: March 31, 2026

The woman on the phone today DEEPLY regrets the compliment she paid to a guy, he took it the WRONG WAY and now Jose and Brooke are gonna have to dig deep for some advice in your Awkward Tuesday Phone Call podcast!See omnystudio.com/listener for privacy information.

You know Roald 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 IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. In 2023, Bachelor star Clayton Eckerd was accused of fathering twins. But the pregnancy appeared to be a hoax. You doctored this particular test twice, Ms. Owens, correct? I doctored the test ones.

It took an army of internet detectives to uncover a disturbing pattern. Two more men who'd been through the same thing. Greg, a lesbian, Michael Mancini. My mind was blown. I'm Stephanie Young. This is love trapped. Laura, Scottsdale Police. As the season continues, Laura,

Laura Owens finally faces consequences. Listen to a love-trapped podcast on the IHeart radio app, Apple Podcasts, or wherever you get your podcasts. I'm Lori Siegel, and on my new podcast, Mostly Human, I'll take you to some wild corners of the tech world. I'm about to go on a date with an AI companion at a real-world cafe right here in New York City. There's no playbook for what to do

when an AI model hallucinates a story about you. Mostly Human is your playbook for how tech can work for you. Anyone can now be an entrepreneur. Anyone can build an app. And it's very empowering. Listen to Mostly Human on the IHeart Radio app, Apple Podcasts, or wherever you listen to your favorite shows. How could this have happened in City Hall?

Somebody tell me that. A shocking public murder. This is one of the most dramatic events that really ever happened in New York City politics. I scream, get down, get down. Those are shots. A tragedy that's now forgotten. and a mystery that may or may not have been political, that may have been about sex.

Listen to Roershack, murder at City Hall, on the IHeart radio app, Apple Podcasts, or wherever you get your podcasts. 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 pleasure for the Big Ten Coach of the Year? Oh, whatever. Would you like to?

Yeah, she don't know. So you're a Spartan, is that what I'm getting here? So whether your bracket is busted, or you just want the real talk on what's happening during the tournament. Open your free IHeartRadio app. Search Playground and Funny with Carrie Champion and Jamel Hill and listen now. Presented by Capital

1, founding partner of IHart Women's Sports. All right, it's your awkward Tuesday phone call and it's brand new. Thank you for joining us here at the podcast. It's Brooke and Jeffrey in the morning. And it's a good one. I hope you enjoy it. But first, let's go to the comment sections.

Jozo said, it's Joseph from Croatia. I love listening to your podcast while I'm touring around the country with my folk band. Oh my gosh. I started listening to your podcast a little while ago and I got hooked since. Love you guys. Take care. If you're ever in a band, shout out your band on the comment section because I always love to go search and hear what you play.

Also shout us out on stage. Like the next song, this is dedicated to Brooke and Jeffrey in the morning. And then you haven't been to a folk show in a while. Oh, yeah. Sorry. This next one is dedicated to Brooke and Jeffrey and then blow on the jug. Yeah. Might get a lot of booze from the crowd, but we apologize in advance.

We hate those guys. Yeah. I want to be in whatever one has her monica. Yeah. I love good harmonica. Please tag. Or like retag. Wait, what am I trying to say?

Tag you. Comment again and put the name of your full campaign. There you go. There you go. All right. Brand new awkward Tuesday. It's starting right now. It's almost time for your awkward call.

It's Brooke and Jeffrey in the morning. Yeah, it is. And today a woman is reaching out to us with deep regret. Uh-oh. Oh, no. For complimenting a man. Oh. I hear you, girl.

Preach. Yeah, the ladies understand. I mean, like, Why would you? Why would you ever do that? Seriously. She made one simple compliment to this dude she was seeing. Yeah?

And he took it the wrong way. Oh, no. So wrong that they're not even hanging out anymore. Oh, no. Yes, it was the worst type of backfire. And now Jose and Brooke are going to have to dig deep for the best advice possible to help this woman change a man's mind. Yeah. Before he goes through with his big plans for tonight.

I'm not very deep, but I'll dig deep. But I'll dig as far as I can get in there. Okay. Wait into that pool, Jose. Let me get you a teaspoon. It's coming up in a brand new awkward Tuesday phone call. Next. It's awkward.

It's Tuesday. It's awkward Tuesday phone call. You know, dating experts say sometimes attraction isn't about looks or personality or even chemistry. What is it? Really? What is left, Jeff? I mean, those things do seem to count for something. But in reality, all it takes is proximity.

You just got to be close to someone. If you're around someone for long enough, they can slowly become your George Clooney. Oh, we did just talk about that. Alexis, didn't you say that about one of our engineers the other day? Sorry. Was it about Dale? Dale. Am I out of him?

I only know them off looks. Sorry. No. He's the hot one. Okay. Anyway, a woman who works in a dentist's office had a patient in close proximity to her. And the rest is an awkward Tuesday phone call. So let's see if we can help her out with it.

Her name is Kate. Kate, welcome to the show. Oh, thank you. I appreciate it. I really need some help. Okay, wait. Kate, are you the... Jeffrey said you work at a dental office?

Yes. I work at the point, yes. Oh, okay. Ah, you're the face of the dentist. Oh, no. The gatekeeper of the appointments. Yes. Okay.

So there was some sort of, according to your email, romantic encounter. her? Well, yeah. It didn't start off that way. This guy just uptake it came in. You're like, I have all your dental charts. Yeah. And then we just like hit it off. I was getting him ready and we were just talking, you know. But I really, like, I found myself smiling when I went back to the front desk. And then later, I found out that he asked my boss for my number. Hey. It was mutual. That's great. So like my boss. was like, oh, my God, do you even have any idea who this guy is? And I was like, no. And he's like, oh, yeah.

Like, he's this huge in tech. And so, you know, of course, I googled him and was like, oh, my God. I see. He was there to give veneers. He's rich, rich. Okay. Yeah, he actually is beautiful teeth. But we did go out.

Great. After he saw how much he was worth. She was going to go out with him anyway, Jeff. She already liked him. I already liked him. Yeah. The conversation was so fun. Okay.

So, I mean, you weren't too nervous going in? I was a little nervous, but, like, he just has, like, a fun presence about him. He's, like, energetic, but also kind of, like, easy going in a way. Like, you just, I felt, like, calm around him. That is such a good sign. Rich guys, like, rich guys are normally all over the place. Yeah.

But it's like how Brooke feels around me and Jose. That's just calming, like, you love being in their. presence all the time. That's exactly the men that popped into my head when I thought about that. That's not my husband. Really sweet of you to say, Brooke. Okay. Sorry, did we get his name? Oh, his name is Jim. Jim. Jim, all right. This isn't a second date, so. Yeah. Do we get into the date or not? Yeah. Tell us what does the awkwardness come into this? Well, okay, so it turns out that he was married for quite a long time and who's been divorced. about a year and he hasn't gone out with anyone in that time.

So I think, you know, he was very not insecure, isn't quite the word, but not. Not comfortable. Yeah. Okay. Okay. On the date, he wasn't super comfortable. He was just like, where do I put my hands? Right.

Exactly. And so just to put him at ease and encourage him, I was like, oh, my gosh, I started joking with him because that's what I love about him. I mean, I shouldn't say I love that. But I really enjoyed it. Uh-oh. Careful. And so he and I, like, were joking.

And I said, you would do so great on the dating apps. And he's like, oh, come on. No, I wouldn't. And I was like, you totally would. You would clean up. That's a joke that could backfire, my friend. Yeah. Boosted him up.

Not only did you boost him up, but you also came across this. Like, if someone said that to me, I'd be like, oh, you're not interested in me romantically. You want me to date other people. No, I know. But, like, we actually had gone out four or five times. Oh, by that point? Yeah, sorry, I didn't mention that So I feel like

By that point I just felt comfortable Riving him because I think we're cool But I think I made a mistake by saying that Why? Why? Because then he texted me about a week after that And he's like, oh my God, you were totally right, you're the best And he's like, I have 20 matches

And out of the 20 matches He has like 15 dates lined up already Yeah, the first one's tonight, you guys. Oh, a lot of info. You don't think that's just part of his hilarious sense of humor that he's joking about that with you. You think for real this is going down? I really do because that would be the worst sense of humor. Okay.

Well, and he followed it up by telling you. So he told you I'm going out tonight with someone? Yeah. He thinks you friends are. Yeah. You wouldn't have a friend to him where you like. No, I get it. It's totally my fault because I was just.

trying to be encouraging to him. So now he does think like I'm his wingman or buddy or something and he even said more. He's like excited. He's like, this is like a new lease on life for me. And he has you to

thank for that. Jeez, Kate. So you definitely, you do sound definitely regretful about what's happened. But yes, why have you reached out for help with an awkward Tuesday phone call? Because I think maybe it would be a good time to call him

and have a really awkward conversation about how I want another shot. I mean, I know it's a long shot, but I feel like if I don't take it, I'll be so mad at myself. Oh, yeah. Maybe he's waiting for this. And he just doesn't get it.

Yeah. You know? Yeah. No, I'm sure every guy wants to say, yeah, I'm going to look past the 15 beautiful women I have dates lined up with and go hang out with my friend. Hey, half those dates are going to bail anyways.

They're going to cancel. He's new to the world. He doesn't realize. That's true. Maybe this is part of the advice that we're going to give you when we come back and let you make your awkward Tuesday phone call to your super rich, wealthy, possible future boyfriend. Yeah, thank you. Hopefully that's what happens with your awkward Tuesday phone call next.

It's awkward. It's Tuesday. It's awkward Tuesday phone call. If you're just joining us, we're about to make a moment. make an urgent call here, trying to stop a guy from going on a date tonight. Yes. And instead, asking him to reconsider our listener, Kate, who accidentally friend zoned herself by telling him he'd be a huge catch on the dating acts.

And he is. Why would she say that to him? Because when they were hanging out, she learned that he got out of a long marriage recently, and he seemed kind of nervous and unsure of himself. Dude, they were four to five dates in. That's like almost the start of like a relationship. I mean, like, that's where you start to decide, like, are we doing this? We're dating.

Yeah, but his nerves were getting the best of him being back in the dating scene. So she tried to lift him up and be positive. And her encouraging words were a little too encouraging. Yep, yeah. Because now he's lined up 15 new dates for himself, one of which happens tonight and Kate wants to try to change his mind. So she needs our help on how to do that. Brooke, what's your advice. This is hard.

You don't want to come off desperate. I think what I would do. No, you don't. You don't. You want to be a catch, right? Yeah. Especially for a guy like this. That's why you fight fire with fire, Kate.

You tell him you have a date tonight with someone super hot. Oh, that is. I was expecting more mature advice for Brooke. No. I was thinking about it. I thought about like, be honest with your feelings. But then that just comes off as clingy. Okay.

I don't know about that one. That seems like that could just be the end of anything. No, listen. In high school, I used to tell these boys that I was. like that other boys from another school are taking me out when really I was just eating banana cream pie with my best friend and you know what I eventually dated that guy that I lied to that is a good one that's one tool in your tool bag that you could use Jose what's your advice you need to get out of the friend zone and the best way that you can do this is to bring up that it's great you got to

experience dates with you but we never finished our lesson oh kissing is not Next. What? Are you regretting calling into this show for advice? Sounds like a friend right now what I'm talking to. Do you want to kiss him or not? I do want to kiss him, but I don't want to be like, I don't know, like a lesson. Maybe.

You haven't kissed after four to five dates? Not yet. Oh, super friend zones. This is worse than I thought. This is bleak. She said that he's nervous about getting back in the dating world. I'm sure he's trying to take it slow too. Yeah, so did my husband?

Slow, whatever. Did you just say my husband and then er in the same sentence? He tried to take it slow too. How did that work out with him? Okay. Well, we're running out of time here, Kate. So we got to make this call. I'm going to dial this guy Jim for you and see if you can convince him to cancel his date plans tonight and choose you instead.

And kiss you. Finally. Oh, my gosh. We'll see. It's up to you how you want to do it, but we're going to be behind you in your corner ready to jump in when you need help. All right, you ready? Yeah, thanks. All right.

Oh, this is going to be so awkward. Let's see how it goes. Hello? Hi. Hello, it's changed. Yikes. Oh. Oh.

Oh. Oh. I'm sorry. Why didn't you call me from your number? Huh? Oh. Just because. Just because I am trying to be mysterious.

Okay. It's messing with you. Anyway, you and me were texting. Why are you coming? Wow, it looks like you got a lot of dates lined up. And I was just like, yeah, I've got a date lined up too. I just wanted to know with somebody. Oh, okay.

Yeah, he was like super hot. Oh. Good. Yeah, I'm glad they're hot. That's great. I mean, I have a date tonight, too, so that's cool. That's cool. I know you do.

I'm just kidding. I don't really have a date tonight. I was just saying that. Can I ask what I'm really trying to be mysterious here. Yeah, go ahead. Go ahead. Ask me anything. No, no, I just did.

Oh, I'm sorry. I didn't hear you. What you say, Jim? I'm asking what's going on? Because you're calling me from a different number. You're acting mysterious. You're talking about dates you have with a hot guy that you don't have. I know.

Are you okay? Yeah, no, I'm fine. I'm fine. I mean, like, physically I'm fine. Emotionally, I feel like kind of a mess. So, like, you know how we, like, went out on four or five dates? Four dates, exactly. Four wonderful.

We went on four dates. Remember? Yeah. I was there. Well, can I just be honest with you? You treated me so well, and I had such a good time, and it was, like, just so fun and effortless, and that's why I started joking with you,

like, about how you do on the dating apps, and I just, I know we haven't kissed or anything, or we didn't kiss, but I think I caught some feelings, and I see that you have all these dates, lined up and I feel like I just want them to be with me. Hold on, hold on. Okay, I think that there's some kind of misunderstanding that's happened. Listen, you know I'm friends with your boss, right?

Yeah. So I was talking to him the other day about you and he said, maybe I'm just too rich for you. You know, and that's what? Some people feel weird. Yeah, like some people feel weird about when other people have money and they don't really know how to act and maybe it made you uncomfortable or something and that maybe we should be friends and I mean like you know I don't want you to be uncomfortable like at the end of the day so like maybe I just have too much money for you.

Wow. No, that's crazy. Yeah, that's not a thing. I would agree with that. Yeah, like I love money. I mean. Oh, okay. Maybe just not like in a way like I just.

I, okay. Yeah, yeah, you need to pump the break a little bit. Wait, what is happening? Hey, Jim. What's happening is you're on a radio show right now. It's called Brooke and Jeffrey in the morning. Like V radio? I'm on V radio.

Sure, you could call it that if you want to. Yeah, V podcast. That's right. And this is called an awkward Tuesday phone call. Kate reached out to us because she was looking for a little bit of advice on how to have this conversation with you. Yeah, she accidentally friends. zoned you. She obviously didn't want to. Oh.

Jim, it's true. And I'm so sorry. I don't even know what else to say. And maybe I shouldn't say anything because I keep digging holes for myself. You do. Okay. And you know what? I never said I can't date a rich guy or I don't like rich guys. Like money's just not the most important thing to me.

But I told my boss, he's taking me all these fancy places. But the thing is that I said, I don't, I like you. I don't care about the money. any part of it. Like, that's not what matters to me. That's what I said. That's a nice thing. Isn't that nice to hear, Jim? Yeah. I mean, that's nice to hear. I mean, a lot of girls with dating after the same thing. Okay, they were lying. Did you put your net worth on the dating ass, Jim? Are you not supposed to? No. Oh, Jim. Well, no, it says, like, what your job is, so I just put in parentheses. No. Let's take that off. Four million base salary. Now I know how you got 20.

matches. Yeah. It makes sense now. Yeah. So, Kate, you want to go out? Yes. Well, that was confident. So, wait, Jim, you like Kate.

You were sad when she brought up the dating apps, it sounds like. No, I was sad when her boss said she didn't like rich guys. Yeah. Oh, man. I didn't say that. That's like a false narrative. Yeah. Misinterpreted.

Kate was screaming that she loves money just a second ago. I think what she's trying to say is money doesn't matter that much to her. She likes the person. And Jim, I like you. Aw. How does that feel, Jim? Yeah, I'm just thinking about all the dates I have to cancel now. Oh.

That's good. I'll do it for you. Oh, wow. So just to confirm, Jim, that's something you're open to because we heard that you're going out with someone tonight. Would you be willing to step back from that and give Kate another chance? Yeah, you're free to me? Oh. Yeah.

All right. Don't forget the kissing lessons. Yeah. I love that. Kissing lessons? I'm sorry, I didn't hear about that. You will, Jim. Kissing's changed a lot since you were married, so get ready for a whole new experience with Kate, okay?

Do I need kissing lessons? You'll find out tonight, dude. Brooklyn Jeffrey in the morning. The newest tracks. Let's go. New music. And the next big thing. Always on the new music first.

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Always first. Stream now on the free. IHard Radio app. You know Roald Dahl, 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 Dahl, 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 I Heart Radio Apple. Apple Podcasts, wherever you get your podcast. You know, I really like that he gave her such a bad time about her phone over and over and over again. You're concentrated on that part? Because you know rich guys don't trust people on burners. Oh. And he was clocking something suspicious happening very early on in the call.

You're right. But he still answered an unknown call. Or you could say divorce A's don't trust anybody on burners, I think is probably more accurate. That might be true. But I am glad to like to. learned that he's such like an easygoing dude because a lot of guys fresh off a divorce like that are just like, oh, you know,

I just want to wear my leather jacket now and only date women with big boobs for a while. But this guy, he was deep. It was amazing. He was like a lovely man. Unfortunately for him, he has too much money, though. You know, it's a crutch. I actually hope we get an update for them.

This could be cute. They were cute. Yeah. We'll see if it continues. We've asked them to stay in touch with the show. And we want you to get in touch with us, too, if you ever need help with, with some awkward situations in your dating life or your personal life,

we can give you the advice, not necessarily to fix it, but, you know, it's advice. To go forward. There you go. You know, Roald 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 Roald 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 Roald Dahl on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

In 2023, Bachelor star Clayton Eckerd was accused of fathering twins, but the pregnancy appeared to be a hoax. You doctored this particular test twice in so much, correct? I doctored the test ones. It took an army of internet detectives to uncover a disturbing pattern. Two more men who'd been through the same thing.

Greg, a lesbian. Michael Mancini. My mind was blown. I'm Stephanie Young. This is Love Trapped. Laura, Scottsdale Police. As the season continues, Laura Owens finally faces consequences. Listen to Love Trapped podcast on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts.

I'm Lori Siegel, and on my new podcast, mostly human, I'll take you to some wild corners of the tech world. I'm about to go on a date with an AI companion at a real world cafe right here in New York City. There's no playbook for what to do when an AI model hallucinates a story about you. Mostly Human is your playbook for how tech can work for you. Anyone can now be an entrepreneur. Anyone can build an app. And it's very empowering. Listen to Mostly Human on the IHeart Radio app, Apple Podcasts, or wherever you listen to your favorite shows.

How could this have happened in City Hall? Somebody tell me that. A shocking public murder. This is one of the most dramatic events that really ever happened in New York City politics. I scream, get down, get down. Those are shots. A tragedy that's now forgotten.

And a mystery that may or may not have been political. That may have been about sex. Listen to Roershack, murder at City Hall, on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. If you're trying to keep up with everything happening on and off the court, we've got you cover. on the podcast, Plagrant and Funny.

You want to start with the first special for the Big Ten Coach of the Year? Oh, whatever. Would you like to? Yeah, she doesn't. So you're a Spartan, is that what I'm getting? Exactly. So whether your bracket is busted, or you just want the real talk on what's happening during the tournament,

open your free IHeart Radio app. Search Plagrant and Funny with Carrie Champion and Jamel Hill, and listen now. Presented by Capital One, founding partner of IHart Women's Sports.