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Brooke
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Jeffrey
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Brooke
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Ryan Seacrest
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Jeffrey
I've never felt like this before. It's like you just get me. I feel like my true self with you. Does that sound crazy? And it doesn't hurt that you're gorgeous. Okay, that's it. I'm taking you home with me. I mean you can't find shoes this good just anywhere. Find a shoe for every you from brands you love like Birkenstock, Nike, Adidas and more at your DSW store or.
Jose
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Jeffrey
To save big 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 gonna 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. Jul 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 know, you're here.
Brooke
That's all we care.
Jeffrey
Cling to your relationships right now because you could be in the same boat as our listener. Yeah, let's get it started. It's our second date update.
Brooke
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.
Jeffrey
What is it going to be?
Brooke
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, Brooks 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?
Jeffrey
I totally do online dating. I would just never do marriage after I did it because I would have never dated anybody long enough.
Brooke
Yeah, yeah, exactly.
Jeffrey
I see what you mean. I thought you meant. Okay.
Brooke
It's the crux of dating with all.
Jeffrey
The apps now, too many choices for people.
Brooke
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.
Jeffrey
I go to the cereal aisle and it feels overwhelming. One I should choose.
Brooke
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.
Jeffrey
Jeff's dream.
Brooke
Yeah, there's positives and negatives to it, but. Evan, welcome to the show.
Evan
Hey, guys.
Jeffrey
Hey, Evan. I'm sorry, man. He sounds like you're going through it with this online dating stuff.
Evan
I am. It's been years, and there's been ups and downs, but I'm just. I want to try something new, and I. I think it's gonna work. I just need a little help.
Brooke
Okay.
Jeffrey
Okay.
Brooke
So what is your. Your stance on dating right now? Like, where are you at?
Evan
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.
Brooke
But you're supposed to, like, date a little bit, and then when one stands out, then you kind of focus on them. It doesn't bode well for Brooks. She focuses a lot on that one guy.
Jeffrey
Yeah, that's so funny.
Brooke
So, Evan, you're. You're not focusing on just one. You're dating a lot of different people?
Evan
Well, I wouldn't say a lot, but, yeah, I'd say a small handful at any given time.
Jeffrey
Wow.
Brooke
Okay.
Jeffrey
That's a lot.
Brooke
A lot for some.
Jeffrey
Is there one in particular that you really like, or are we just going to call 10 girls?
Evan
Yeah, there is one. Her name's Jenna, and she's a top contender.
Brooke
Top contender.
Jeffrey
Is that a compliment, Alexis? Yeah, I want to be. Oh, it is. I mean, if I'm going to be all contender, I want be the top one.
Brooke
There you go. So where do you and Jenna stand?
Evan
We had one date. It was good, and nothing bad happened. And, like, I know how these.
Jeffrey
Is that your bar 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?
Evan
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 it a little bit.
Jeffrey
Oh, what?
Brooke
Wait, hold on. So you already wait, like, she's hooked.
Jeffrey
So you're not calling us because someone's not calling you back or isn't interested?
Evan
Correct. She is interested. That's what I believe.
Jeffrey
What?
Brooke
Okay, this is different, I guess. Let's hear him out. So this girl.
Jeffrey
Try not to think game. He's playing games in my head right now.
Evan
It's not a game, but it is reverse psychology.
Jeffrey
Oh, that works so good on me.
Brooke
Did it just work on you? I'm trying to figure this.
Jeffrey
I'm not gonna tell you. I love it.
Brooke
All right, you already have Brooks interest now, so what is your idea for reverse psychology with Jenna?
Evan
I want you to call her and tell her that, like, I thought that she was cool, but I'm a little on the fence about it.
Jeffrey
Huh.
Brooke
Wait, why?
Jeffrey
Why would we be calling her? Just to tell her that. Yeah, that's gonna make her morning. It's gonna really.
Brooke
It's kind of weird. Why do you want to do it this way with Jenna?
Evan
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.
Jeffrey
You're getting friend zoned is what it sounds like.
Evan
It makes me feel like I need to be defensive and prove myself because she's in the power position.
Brooke
So I see you're good at the first couple dates, which is.
Jeffrey
No, just the first one. It sounds like.
Brooke
Yeah. 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 and be like.
Jeffrey
Leave our friend alone. Here's the thing. You sound like a genuinely nice guy, and that's probably why this is happening. I don't mean to be mean.
Brooke
Did you see Alexis gag when you said genuinely nice guy? That's the problem here.
Jeffrey
Now everything makes sense. I mean, you do know this couldn't backfire, right?
Evan
I have nothing to lose at this point, trust me.
Brooke
I mean, it is a bold move, you have to admit.
Jeffrey
Can you tell us anything about Jenna that would make you feel like this is going to work on her? Like, what does she, like? Would you do?
Evan
I could tell you, but she's literally 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 going to turn on me. She's going to turn.
Brooke
Exactly. 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.
Jeffrey
Here's my thing. Like, we tell her this statement and then what, Jeff? Like we tell her, hey, so and so isn't into. Yeah, how do we follow up that conversation?
Brooke
You know what? He is on the other line right now. So, like, maybe if you want to try to convince him to go out, he might be okay.
Jeffrey
So, like, we won't do a lot of the talking.
Brooke
No, I think Evan wants to be in control here, so.
Jeffrey
Okay. Like the bad boy Evan is. Oh, he's not interested. But had time to call the radio, wait on hold and sit and listen. Okay.
Brooke
Hello?
Jeffrey
No, he's not going to say hello. He's going to say sup?
Brooke
Oh, I forgot I was in the.
Jeffrey
Middle of the phone call.
Brooke
We're just going to be super non committal about it and let Evan swoop.
Jeffrey
In for entertainment purposes. I'm in.
Brooke
I think it's an interesting experience 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, man. 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.
Jeffrey
It's not an idea any of us have ever had.
Brooke
Probably too smart for our simple brains.
Jeffrey
Oh, I like that spin.
Brooke
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.
Jeffrey
Are you giving yourself the ick?
Brooke
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?
Jeffrey
Oh, man.
Brooke
Basically reverse psychology Jenna into loving him.
Jeffrey
I'm going to be so disheartened if this works. Like, you can't just be open with your emotions. Emotions anymore.
Brooke
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.
Jeffrey
This is the only problem, bro. Because why People aren't liking the dates with him.
Brooke
He's trying to stop the cycle of what's going on in his life. Right, Evan?
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.
Jeffrey
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.
Brooke
Right, exactly. And he thinks that if he does it this way, then she's going to be more open to not just the second date, but the third date, the fourth date. How cool do we play it? Jeff? I'm worried. Like, do we. Do we get her name wrong at first on. Oh, sorry. 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 date. We'll just go right to that.
Evan
Okay.
Brooke
I like that. Sound like a good plan. Yeah. Deafening silence from the room. Okay, here we go.
Jeffrey
I thought we already knew the plan.
Brooke
Okay, let's try it.
Jenna
Hello?
Brooke
Hey, is this Jenna?
Jenna
This is who's calling?
Brooke
We're a radio show actually, called Brooke and Jeffrey in the Morning.
Jeffrey
Hey, Jenna. Hi.
Jenna
Hi.
Brooke
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.
Jenna
Yes, but where you guys are calling.
Jeffrey
Me, we're kind of surprised. We're calling you too for this segment because it doesn't actually fit.
Brooke
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.
Jenna
Okay. Yeah, yeah.
Brooke
Remember going out with Evan?
Jenna
I do.
Brooke
Okay.
Jenna
Yeah, I do.
Brooke
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. Yeah.
Jenna
What? He said that he's just.
Brooke
He raising. Yeah, like he enjoyed the date, no question about it, but the future he's a little bit uncertain of.
Jenna
Wait, so he doesn't like me? I.
Jeffrey
No, no, no, no. He doesn't not like you. He just doesn't. He's like, doesn't know you.
Brooke
Yeah. His heart is congested.
Jeffrey
What?
Brooke
Confused. I don't know. He.
Jeffrey
He doesn't know plaque in the arteries.
Brooke
Now tell what I meant. He doesn't know where his mind is at a hundred percent. He's trying to figure stuff out.
Jenna
I guess I'm just confused. I thought we liked each other. I thought everything.
Brooke
Would you say specifically that he liked you or did you just feel the vibe?
Jeffrey
Nobody does that anymore. What did he write a note and circle yes or no? Do you like.
Brooke
Yeah, it would make it a whole lot easier.
Jeffrey
Yeah.
Brooke
But, hey, glad you're on the date. I like you so far. No, sometimes it's hard to know how people feel. Sometimes you're reading signs, you're reading them wrong.
Jenna
No, no, we had a great time. We even kissed.
Brooke
Okay, well, that's good. Like, tell us more of stuff like that. Like, what exactly happened? Well, give us more indications of why you think he liked you so out.
Jeffrey
Of the box right now.
Jenna
Well, I mean, we grabbed 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.
Jeffrey
Or she thinks they're nice, but to be. I think that's more.
Brooke
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.
Jenna
Honestly, this is just extremely disappointing to hear because we were vibing.
Brooke
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.
Jeffrey
Makes him feel like he wants it more.
Brooke
Yeah.
Jeffrey
You know, I'm just gonna say that.
Brooke
I will say he does want to talk to you, though.
Evan
Yeah.
Jenna
What?
Evan
Hi, Jenna.
Jenna
Evan, what is going on? I'm so confused.
Evan
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 sure.
Jenna
Huh. Okay. Well, I guess. I guess maybe we're just better off friends.
Brooke
Well. Well, hold on.
Jeffrey
What are you doing, dude?
Evan
I don't. 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. This is weird.
Jenna
This is a very strange way of going about this.
Jeffrey
I don't even understand what he's trying to go here.
Brooke
Evan, you're saying. You're saying that she's saying that she likes you, but you're not sure if you believe that.
Evan
Not completely, because I'm a nice guy, and I have a hard time believing that she really likes that.
Jeffrey
I thought you just said you weren't attracted to her because there was no romantic connection for you.
Evan
I'm not saying there isn't. There isn't. I'm not sure. I'm in the middle here.
Brooke
Oh. Okay.
Jeffrey
Your message, I think, is getting a little lost.
Brooke
Yeah. Well, Jenna, maybe you have to show him a little bit more strongly that the feelings are there that it's worth.
Jenna
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.
Brooke
You see, one date, they're saying they like him, and then all of a sudden, something switches. And they're like.
Jeffrey
The thing that switches is you telling her ye. There's no romantic 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.
Jenna
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. This is what's turning me off.
Brooke
Oh, no.
Evan
It would have happened on the second or third date anyway.
Brooke
Yeah, Jenna, you may not realize this now, but after three dates with him, you would realize that you weren't into him.
Jeffrey
Now we're gonna tell her how she's gonna feel on a future date.
Brooke
Unless we're wrong, because. 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. At least seven is. You might want to plead your case to him right now, Jenna. And ask Evan out.
Jeffrey
After he turned her down.
Evan
I wanna. I want a partner who will fight for me.
Brooke
Okay.
Jeffrey
After one date.
Brooke
That's respectable. I think it's a. Are you willing to fight for him, Jenna, right now?
Jenna
To be honest with you? No.
Jeffrey
I mean, you have nothing else to lose at this point. Evan, why don't you just tell her the truth?
Jenna
Evan, 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.
Evan
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 like 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 really work towards winning me. Oh, I'm usually the one that's trying to win somebody over, and I. I wanted to flip the script.
Jeffrey
Oh, buddy.
Jenna
I mean, thank you for being honest, finally, about this. It was weird. It was a weird way of going.
Jeffrey
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. He. I think he is finally understanding that.
Evan
Yes.
Jenna
Yeah.
Brooke
Now that. 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.
Jeffrey
Pretend this never happened. Yeah.
Evan
Yeah, I promise. No games going forward.
Brooke
That's a problem.
Jeffrey
Come on, Jenna. Don't hate the player, hate the game. Let's go one more date. What happens? We're the game. No, no. Yeah, we're the game.
Jenna
I'll go on a date.
Brooke
Reverse psychology does work.
Jeffrey
No, the honest truth works, Jeff. Your real feelings work.
Brooke
I like how we feel accomplished when literally nothing changed. Yeah. We did it.
Evan
You guys are the best. Thank you.
Brooke
Oh, you're welcome, buddy.
Jeffrey
Hurt my brain. I don't feel like it either.
Brooke
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.
Jeffrey
Yeah, no, I mean, we literally just. We added more drama.
Brooke
We did.
Jeffrey
And there was no need for it.
Brooke
This is what happens when us non cool guys try and play cool.
Jeffrey
Yeah. You know what I mean. That's right, Jose. Be yourself. Yeah, it is.
Brooke
It's a nice dude.
Jeffrey
Be a nice dude.
Brooke
It's a win for nice guys everywhere. And he's lucky that for some. Some weird reason, she just liked him for who he was.
Jeffrey
Dude. But I really don't want to get an update from them that on the third date she decided there was no romantic connection.
Brooke
Yeah, he's just. He's just too nice, Right? Or.
Jeffrey
So we need to talk to all the girls and find out what's the real reason, what he's really doing.
Brooke
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 podcast at Brooke and Jeffrey and on YouTube.
Jeffrey
Brooke and Jeffrey in the morning.
Ryan Seacrest
Hey, it's Ryan Seacrest for Albertsons and Safeway with the stock up sale at Safeway and Albertsons. Stock up and earn four times points at your local store when you purchase participating products. Save on household essentials from General Mills, Kellogg's, Philadelphia Quaker and Tide. Clip the offer in the app for event savings and look for participating items throughout the store. Shop in store or online. Plus you can even have your groceries delivered or use. Drive up and go to have your groceries brought to your car at the store. Restrictions and exclusions applied. Visit Albertsons or Safeway.com for more details.
Jose
Spring has officially sprung and we're craving even more sunshine. The solution? A cheap Caribbean beach vacay. Cheap Caribbean is all about finding you the best beach deals for your budget. Check out their semi annual sale and take an extra $200 off site wide vacation packages of four plus nights to your favorite tropical beach destinations. Don't wait. This awesome offer won't last forever. Go to cheapcaribbean.com to start your search for paradise and book before April 30th.
Jeffrey
To save big PayPal lets you pay all your pals like your graduation gifters. Who's paying for the mattress topper? You mean the beanbag chair? Aren't we getting a mini fr?
Ryan Seacrest
Can we create a pool on PayPal?
Brooke
It lets us collect the money before we buy.
Jeffrey
Ooh yes, that's smart.
Jenna
Glad we can agree on something easily.
Jeffrey
Pool split and Send Money with PayPal. Get started in the PayPal app. A PayPal account is required to send and receive money. A balance account is required to create a pool.
Ryan Seacrest
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Brooke
Painful Thoughts 20 more minutes to kill in the pharmacy before my prescription is ready. Maybe I'll grab some deeply discounted out of season Halloween candy. I never had a chocolate pumpkin with raisins before. Those were raisins, right? Next time use Amazon Pharmacy. We deliver. And no, those were not raisins. Amazon Pharmacy Healthcare just got less painful.
Podcast Summary: Brooke and Jeffrey: Second Date Update – "3rd Times A Yawn"
Release Date: April 4, 2025
Introduction
In the April 4th episode of Brooke and Jeffrey: Second Date Update, hosted by iHeartPodcasts, Brooke and Jeffrey delve into the complexities of modern dating through the lens of one listener's innovative approach. Titled "3rd Times A Yawn," the episode explores Evan's unique strategy to break free from the dreaded friend zone using reverse psychology. The hosts engage in lively discussions, provide insightful commentary, and ultimately offer a firsthand demonstration of Evan's method by involving his date, Jenna, in a live segment.
Listener Evan’s Dating Dilemma
The episode kicks off with listener comments, including a humorous note from Jul Stanford about clinging to her relationship after hearing the show's dating tales. Brooke and Jeffrey then introduce Evan, a listener who has faced challenges in the online dating scene. Evan shares his frustrations with the overwhelming number of options available through dating apps, leading to indecision and difficulty in forming meaningful connections.
"She's always like, oh, I don't think I could ever do online dating. There's way too many options. How could you ever just pick one guy?" [03:28]
Evan explains that while he enjoys dating a small handful of people simultaneously, he often ends up feeling undervalued and friend-zoned. Determined to change his pattern, Evan proposes a bold move: leveraging reverse psychology to secure a second date with his top contender, Jenna.
Brooke and Jeffrey’s Strategy Session
Brooke and Jeffrey thoughtfully consider Evan's approach, debating its potential effectiveness and ethical implications. Jeffrey muses, "It's kind of weird. Why do you want to do it this way with Jenna?" [07:32], highlighting the unconventional nature of Evan's plan. Despite their reservations, the hosts agree to assist Evan by enacting his strategy on-air, aiming to provide both entertainment and a real-world test of the method.
Executing Reverse Psychology: Calling Jenna
In a pivotal moment, Brooke and Jeffrey initiate the call to Jenna, Evan's date. They present Evan's conflicted emotions, conveying that while he enjoyed their date, he's uncertain about pursuing a romantic connection. This scripted interaction is Evan's attempt to create a sense of doubt, encouraging Jenna to "sell" herself to win his affection.
"I'm just not totally sure that there's a romantic connection between us." [15:12]
Jenna responds with confusion and disappointment, expressing that she believed there was mutual interest, especially after sharing intimate moments like a kiss. As the conversation unfolds, Evan steps in to clarify his feelings, ultimately revealing his genuine interest in Jenna and abandoning the reverse psychology tactic.
"The truth is, I really like you. I wanted to flip the script." [18:06]
Outcome and Reflections
The live interaction culminates in Jenna agreeing to a second date, demonstrating that honesty far outweighs manipulative strategies in fostering genuine connections. Brooke and Jeffrey reflect on the outcome, acknowledging that Evan's initial plan introduced unnecessary drama but ultimately highlighted the importance of sincere communication.
"Reverse psychology does work." [19:33]
"No, the honest truth works, Jeff. Your real feelings work." [19:34]
The hosts commend Evan for his honesty, emphasizing that being oneself is the most effective approach in dating. They conclude that while Evan's experiment added excitement to the show, it also reinforced the value of straightforwardness in building lasting relationships.
Conclusion
"3rd Times A Yawn" serves as both an entertaining and educational episode, showcasing the trials and triumphs of navigating modern romance. Brooke and Jeffrey successfully illustrate that while innovative dating strategies might offer temporary intrigue, authenticity remains the cornerstone of meaningful connections. Listeners are encouraged to reach out with their own dating challenges, reinforcing the show's mission to blend humor, advice, and real-life experiences in the pursuit of love.
For more engaging episodes and dating insights, tune into Brooke and Jeffrey on iHeartRadio, Apple Podcasts, or Spotify.