Brooke and Jeffrey: Second Date Update - Second Date Update: 3rd Times A Yawn

Episode Date: April 4, 2025

The guy on the phone today told us he’s fed up with being friend-zoned, and he wants to get ahead of things with a bizarre new plan we’ve never tried before! Catch what it is in a new Second Date Update!See omnystudio.com/listener for privacy information.

Hey all you women's hoops fans, and folks who just don't know yet that they're women's hoops fans. We've got a big week over at Good Game with Sarah Spayne as we near the end of one of the most exciting women's college basketball seasons ever. The most parody we've seen in years, with games coming down to the wire and everyone wondering which team will be crowned national champions this weekend in Tampa. Listen to Good Game with Sarah Spayne on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts.

Imagine you're scrolling through TikTok. You come across a video of a teenage girl, and then a photo of the person suspected of killing her. It was shocking. It was very shocking. Like that could have been my daughter. Like you never know. I'm Jen Swan.

I'm the host of a new podcast called My Friend Daisy. It's the story of how and why a group of teenagers turn to social media to help track down their friend's killer. Listen to My Friend Daisy on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. What's up, I'm Laura, host of the podcast Courtside with Laura Corenti,

a masterclass case study of the business of women's sports. I'll be chatting with leaders like tennis icon Alana Kloss. I don't do what I do only for women. I do it for everyone. And I want the whole market. And innovators like Jenny Nguyen. I would say 50% of the people that come visit the Sportsbra aren't sports fans. They come to be in community. They come to be part of this culture. Courtside with Laura Karenty is an iHeartWomen Sports production in partnership with Deep Blue Sports and Entertainment.

Listen to Courtside with Laura Karenty on the iHeart radio app, Apple podcasts, or wherever you get your podcasts. Presented by Elf Beauty, founding partner of iHeartWomen Sports. Are your money skills total trash? Well, trust me, you are not alone. Personal finance ignorance is as American as apple pie, but you can improve. Think, Matt, if your emergency fund was invested,

especially given the volatility we're experiencing right now. Ouchies. Investing, it is ultimately a necessity, but you gotta keep that emergency fund accessible. It needs to be cash parked in your savings. It's time to learn and How to Money is here to bring the knowledge. Listen to How to Money on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts.

Have you ever wondered if your pet is lying to you? Why is my cat not here? Am I going and she's eating my lunch? Or if hypnotism is real? What you would use as a suggestion in order to enhance your cognitive control. But what's inside a black hole? Black holes could be a consequence of the way that we understand the universe Well, we have answers for you in the new I heart original podcast science stuff Join me or hitch him as we answer questions about animals space our brains and our bodies So give yourself permission to be a science geek and listen to science stuff on the iHeart video app, Apple Podcasts, or wherever you get your podcasts. Thanks for being on the second date podcast. It's

Brooke and Jeffrey in the morning and man today's second date is brand new. It's about this guy who has a new plan to stop being friend zone. It was interesting. It was interesting. We tried. We tried for him. We're going to find out if we are successful or not here in just a second. But first some comments from our lovely, lovely listeners. Yes, this one made me laugh. Julianne Stanford said, I was seriously considering divorce until I heard the dating nightmares on the show. Now I'm clinging to my relationship like it's a lifeboat.

I'm like, am I happy for Julianne or not? You're here, that's how we care. Cling to your relationships right now because you could be in the same boat as our listener. Let's get it started. Cling to your relationships right now, because you could be in the same boat as our listener. Yep. Let's get it started. It's our second date update. Second date update.

I'm going to share something with our audience that's happened behind the scenes here. It's Brooke and Jeffrey in the morning. Uh-oh, what is it going to be? I don't remember if Brooke has said this on the air. And it's not bad, but off the air. Whenever somebody brings up online dating, Brooke's response, and Jose, Alexis, you can confirm this.

She's always like, oh, I don't think I could ever do online dating. There's just, there's way too many options. How could you ever just pick one guy? Oh, I can totally do online dating. I would just never do marriage after I did it. Cause I would have never dated anybody long enough. Yep.

Yeah. Confirming what we're saying. Exactly. I see what you mean. I thought you meant... okay. It's the crux of dating with all the apps now. Yeah, there's too many choices for people. And I think it was intended in a good way to match people up who would have never found each other if they were just left to their normal lives. But more often than not, it just ends up being with you have

So many choices men and women can't make up their mind They can't commit to just one and if they're not blown away immediately There's you know 20 other options that they could just go explore. I go to the cereal aisle and it feels overwhelming And the thing is that's where our listener Evan is at right now. He claims he is a victim of being just one guy in a sea of a billion dudes. Oh yeah.

Jeff's dream. Yeah. There's positives and negatives to it, but Evan, welcome to the show. Hey guys. Hey Evan, I'm sorry man. He sounds like you're going through it with this online dating stuff.

I am, it's been years and there's been ups and downs but I'm just, I wanna try something new and I think it's gonna work, I just need a little help. Okay. Okay guys. So what is your stance on dating right now? Like where are you at? I think that you should date a lot of different people because experts say that if you focus too much on just one person you're gonna end up disappointed

And then when one stands out then you kind of focus on them doesn't bode well for Brooks married Yeah So Evan you're you're not focusing on just one you're dating a lot of different people Well, I wouldn't say a lot but yeah, say a small handful at any given time Is there one in particular that you really like or we just gonna call ten girls There is one her name is Jenna and she's a top contender And she's a top contender. Top contender. Top contender.

Can we get that? Is that a compliment, Alexis? Yeah. I like to be. Oh, it is. I mean, if I'm going to be all contender, I want to be the top one. There you go.

So where do you and Jenna stand? We had one date. It was good. And nothing bad happened. And I like, I know how to use these. Is that your bar? Sorry, he says it defensively. Nothing bad happened.

I mean, is that your bar? Like, you had a good enough date that nothing bad happened? So that's why you want to call her Well, sometimes I do feel that way, but this was a good day It was genuinely good and I do believe that she likes me and would like to go out on another day with me I just want to try this thing to kind of make her work for a little bit this thing to kind of make her work for a little bit. Oh no. What? Wait, so you already feel like she's hooked.

So you're not calling us because someone's not calling you back or isn't interested. Correct. She is interested. That's what I believe. Oh, what? Okay. This is different. I guess let's hear him out.

So this girl- Try not to think game. He's playing games in my head right now. It's not a game, but it is reverse psychology. Oh, that works so good on me All right, you already have Brooks interest now, so what is your idea for reverse psychology with Jenna? I want you to call her and tell her that like like I thought that she was cool, but I'm a little on the fence about it.

Huh? Wait, so why? Why would we be calling her just to tell her that? Yeah. That's gonna make her morning. It's gonna be really good. That's kinda weird, guys. Why do you want to do it this way with Jenna?

The thing is I've had a lot of dates this past year where the first meeting is great but then it just it fizzles out. Okay. And the girl will say to me hey you're super cool and everything but there's just not a strong enough of a connection for me. You're getting friend-zoned is what it sounds like. It makes me feel like I I need to be defensive and prove myself because she's in the power position. So okay. Oh I see. You're good at the first couple dates which is. No just the first one it sounds like.

Yeah. Since after that. He wants to flip the script on these women and he wants to be in the power position being like hey like I think you're cool and everything but I don't know if it's there then the girl will have to sell herself to him. So we should call him and be like leave our friend alone lady. Girl will have to sell herself to him You sound like a genuinely nice guy and that's probably why this is Alexis gag when you

Mean you do know this could backfire right I have nothing to lose at this point trust me It is a bold move you have to admit Can you tell us anything about Jenna that would make you feel like this is gonna work on her? Like what does she like? What'd you do? I could tell you but she's like every other girl that I've been dating recently Like, you know, she's sweet. She's funny. She's pretty like they all are. Yeah, but she's gonna turn on me. She's gonna turn Like they all are. Yeah, but he's gonna turn on me. She's gonna turn Let's not get caught up in the minutiae of who she is as a person I don't know if this strategy would actually work. It sounds kind of manipulative Similar to one of my co-hosts and they're happily married so It might actually be a good strategy at the end of the day

Here's my thing like we tell her this statement, and then what, Jeff? Like we tell her, hey, so and so. Is it into you? Yeah, how do we follow up that conversation? You know what, he is on the other line right now, so like maybe if you wanna try to convince him to go out, he might be up for it. If you're thirsty enough. We won't do a lot of the talking.

No, I think Evan wants to be in control here, so. Okay, like the bad boy Evan is. Who's not interested but had time to call the radio, wait on hold, wind around, and sit and listen. Alexis, okay. No, he's not gonna say hello, he's gonna say sup. Oh, I forgot I was in the middle of a phone call. We're just gonna be super noncommittal about it and let Evan swoop in. For entertainment purposes I'm in. I think it's an

interesting experiment at the very least and we're gonna find out how it goes when we call her in your second date update right after this. Hold on then. Second date update. If you're just joining us for the second date our listener Evan has asked us to do something that we've never really tried on this segment before Not an idea any of us have ever had no probably too smart for our simple brains But he wants us to call his date Jenna and instead of saying he had a lot of fun with you He really likes you. He wants to see you again coming on kind of strong even me saying that Are you giving yourself the egg? I kind of strong, even me saying that. Well, that's just normal. Are you giving yourself the ick?

I kind of am, even that, it does feel like a lot. That's why instead Evan wants us to say, he reached out, but he's kind of on the fence about it, not really sure how he feels, so I don't know, how are you feeling about him? Oh man. Basically reverse psychology Jenna into loving him. I'm gonna be so disheartened if this works.

Like you can't just be open with your emotions anymore. Well, Evan has been rejected so many times He's tired of being put on that side of the conversation. He wants to have the upper hand this time This is the only problem bro. It's why people aren't liking the days with him He's trying to stop the cycle of what's going on in his life, right Evan? It's time I gotta stand up for the pack, you know? And there's this storyline that's just been playing over and over again. I think you could have used the quote about, like, how someone who does the same thing over and over again

but expects a different result is the definition of insanity. True. Right? Yeah. Exactly. So you're doing something new. And he thinks that if he does it this way, then she's going to be more open to not just a second date, but the third date, the fourth date. So how How cool do we play it Jeff? I'm worried like do we do we get her name wrong at first?

It's a good question but I think we just have to play kind of non-committal and more just ask her about what she thinks about the day we'll just go right to that. Okay I like that. Sounds like a good plan. I want you to be talking, yeah. Deafening silence from the room. Okay, here we go. I'm nervous. I thought we were already into the plan. Okay, let's try it. Hello?

Hey, is this Jenna? This is. Who's calling? We're a radio show, actually, called Brooke and Jeffrey in the morning. Hey, Jenna. Good morning. Hi. Thanks for picking up.

We're doing a radio show. We're doing a radio show. We're doing a radio show. We're doing a radio show. We're doing a radio show. We're doing a radio show. We're doing a radio show. We're doing a radio show. We're doing a radio show. We We're a radio show actually called Brooke and Jeffrey in the morning. Hey Jenna Hi, thanks for picking up. We're doing a segment on our show. You may have heard of it before it's called a second date update Yes

But where you guys are calling me we're kind of surprised we're calling you too. Yeah Yeah, actually fit. Yeah. Yeah, this is a little bit different than what we normally do But we got an email from one of our listeners that you went out with his name's Evan Okay Yeah, yeah, remember going out with Evan. I do. Okay. Yeah, I do Evan emailed our show he told us that the two of you went out and, you know, he had a decent time. He's considering seeing you again, but he is kind of on the fence about it. Hmm, yeah.

What? He said that? Mm-hmm. He's just... Just paraphrasing. Yeah, like, he enjoyed the date. No question about it, but the future he's a little bit uncertain of. Wait, so he doesn't like me I know he doesn't not like you he just doesn't know yeah his heart is congested what confused I don't know he doesn't know black in the

arteries that's not what I meant he doesn't know where his mind is at a hundred percent He's trying to figure stuff out I guess I'm just confused. I thought we liked each other I thought everything would say specifically that he liked you or did you just feel the vibe? Nobody does that anymore what did he write a note in circle? Yes or no? Do you like it? I like you Circle yes or no do you like Sometimes you're reading signs you're reading them wrong no no we had a great time we even kiss okay Well, that's good. Tell us more stuff like that like what exactly happened Will give us more indications of why you think he liked

Well, I mean we grab drinks I got to really know him he was super super nice I Don't really go out with nice guys. So he was the first nice guy in a very long time in a very long time. Hey! Or she thinks they're nice but they turn out not to be. I think that's more... Oh! Maybe you thought that he liked you but he never actually said that to you? Could just be like a vibe that you were getting?

Honestly, this is just extremely disappointing to hear because we were vibing. Okay, well maybe the vibe that you're feeling from him is the literal phone line connection that is happening right now because he is listening to this call. Makes him feel like he wants it more. Yeah I will say he does want to talk to you though. What? Hi Jenna. Evan what is going on? I'm so confused. Yeah I'm sorry to throw a loop in things, but you thought I was nice? Yeah, I thought you were really nice, too but

I'm just not totally sure that there's a Romantic connection between us. I'm just not really Huh? Okay. Well, I guess I guess maybe we're just better off friends. Well, hold on. Evan, what are you doing, dude? I don't think we should jump to that. I just, I need to be sure that you really do feel that way before I carry on. This is a very strange way of going about this. I don't even understand why he's trying to go here.

Evan, you're saying that she's saying that she likes you, but you're not sure if you believe that? Oh. Not completely, because I'm a nice guy, and I have a hard time believing that she really likes that. I thought you just said you were attracted to her, because there was no romantic connection for you.

I'm not saying there isn't there isn't I'm not sure I'm in the middle here. Okay, your message. I think is getting a little lost Yeah, Jenna, maybe you have to show him a little bit more strongly that the feelings are there that it's worth it After all this Why would I do that? I mean this was it was going so well without even getting anyone else involved This is like turning me away. You see one date They're saying they like him and then all of a sudden something switches Connection and that you weren't sure if you liked her or not. That's the switch you can turn that back

You can be honest about where you stand Yeah, I would have never been weirded out as I am right this moment if you just didn't do all this This is very strange. What's turning me off? It would happen on the second or third date anyway Realize this now, but after three dates with him you would realize that you weren't into him now We're gonna tell her how she's gonna feel on a future date? Unless we're wrong. You're welcome.

Unless we're wrong because normally at this time I would offer to send you guys out and we would pay for it but I kind of have a vibe that both of you are still on the fence. You might want to plead your case to him right now Jenna and ask Evan out. What? You want me to ask her to plead after he turns her down? I want a partner who will fight for me. Oh, Rob, what's up? You reject her?

After one date? That's respectable I think. Are you willing to fight for him Jenna right now? To be honest with you, no. I mean you have nothing else to lose at this point Evan. Why don't you just tell her the truth? I mean, what is this truth? You have to tell me this is the very insane that how this is working out right now.

If you have to tell me something, I mean, you might as well tell me right now. Look, the truth is, I really like you and I was and I was afraid that if I just carried on being nice and showing that I really liked you, that you would get bored of me. And if I use reverse psychology on you, then you would think that I was a bad boy or like something that you're really attracted to and want to like really work towards winning me. I'm usually the one that's trying to win somebody over and I wanted to flip the script.

Oh, buddy. I mean, thank you for being honest, finally, about this. It was weird. It was a weird way of going about it, but. He was just trying something new. Dating's hard these days and he liked you and he didn't know how to keep it going. And it wasn't the smartest move

Yeah, I think he is finally understanding that yes Now that we've really sold him We'd love to offer to send you guys out on another date Jenna, and we would pay for it I mean he has finally come clean He's told you the truth and no more games going forward at least not from Evans Park. Pretend this never happened. Yeah, I promise no games going forward. That's a promise! Come on Jenna, don't hate the player, hate the game! Let's go!

One more day! We're the game! No, no! Yeah, we're the game. I'll go on the date. Yay! Alright! Reverse psychology does work. No, the honest truth works, Jeff.

Your real feelings work. I like how we feel accomplished when literally nothing changed. We did it! You guys are the best, thank you. Oh, you're welcome, buddy. This hurts my brain. I don't feel like it after either, Alexis. Brooke and Jeffrey in the morning.

I don't think there's any way she would have said yes if Evan didn't finally come clean and just be honest about his true feelings at the end there. Yeah, no. I mean, we literally just, we added more drama. We did. And there was no need for it. This is what happens when us non-cool guys try and play cool. Yeah.

You know what I mean? That's right, Jose. Be yourself. Yeah. You're a nice yeah it's a nice dude be a nice dude it's a win for nice guys everywhere and he's lucky that for some weird reason she just liked him for who he was I really don't want to get an update from them that on the third date she decided there was no romantic connection yeah he's just too nice so we need to talk to all the girls to find out what's the real reason, what he's

really doing. Or he keeps up the act and he shows up an hour late to the date trying to be cool, right? Yeah, that's right. But you know what? If you're a nice guy or if you're a bad boy or anything in between, we will help you with your dating life. Email the show. We'll call that person who's not calling you back.

Go check out all of our second dates wherever you get your podcasts at Brooke and Jeffrey and on YouTube. Brooke and Jeffrey in the morning. Hey all you women's Hoops fans and folks who just don't know yet that they're women's Hoops fans. We've got a big week over at Good Game with Sarah Spain as we near the end of one of the most exciting women's college basketball seasons ever. The most parody we've seen in years with games coming down to the wire and everyone wondering which team will be crowned women's college basketball seasons ever. The most parody we've seen in years, with games coming down to the wire and everyone wondering which team will be crowned national champions this weekend in Tampa. Listen to Good Game with Sarah Spayne on the iHeart

radio app, Apple podcasts, or wherever you get your podcasts. Imagine you're scrolling through TikTok, you come across a video of a teenage girl, and then a photo of the person suspected of killing her. It was shocking. It was very shocking. Like that could have been my daughter. Like you never know. I'm Jen Swan. I'm the host of a new podcast called My Friend Daisy. It's the story of how and why a group of teenagers turn to social media to help track down their friend's killer. Listen to My Friend Daisy on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

What's up? I'm Laura, host of the podcast, Courtside with Laura Corenti, a masterclass case study of the business of women's sports. I'll be chatting with leaders like tennis icon, Alana Kloss. I don't do what I do only for women. I do it for everyone, and I want the whole market. And innovators like Jenny Nguyen.

I would say 50% of the people that come and visit the Sports Bra aren't sports fans. They come to be in community. They come to be part of this culture. Courtside with Laura Karenty is an iHeart Women's Sports Production in partnership with Deep Blue Sports and Entertainment. Listen to Courtside with Laura Karenty

on the iHeart radio app, Apple podcasts, or wherever you get your podcasts. Presented by Elf Beauty, founding partner of iHeart Women's Sports. Hey there, Ed Helms here, host of Snafu, your favorite podcast about history's greatest screw ups. It's the 1920s, prohibition is in full swing swing and a lot of people are mysteriously dying? Assistant Attorney General Mabel Walker Willebrandt is becoming increasingly desperate in forcing prohibition.

She was a lone warrior. I mean, how could Mabel not be feeling the pressure? Her bosses are drunks, her agents are incompetent, even Congress is full of hypocrites. So if Mabel is going to succeed in laying down the law, she needs to make the consequences for drinking hurt a lot more. Which she does. Arguably a little too well. Find out more on season 3 episode 4 of Snafu Formula 6.

Listen and subscribe on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Are your money skills total trash? Well, trust me, you are not alone. Personal finance ignorance is as American as apple pie, but you can improve. Think, Matt, if your emergency fund was invested, especially given the volatility we're experiencing right now.

Ouchies. Investing, it is ultimately a necessity, but you gotta keep that emergency fund accessible. It needs to be cash parked in your savings. It's time to learn, and How to Money is here to bring the knowledge. Listen to How to Money on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts.