Brooke and Jeffrey: Second Date Update - Second Date Update: Best Date of My Life

Episode Date: June 18, 2025

The kiss that happened at the end of our listener's date was either the cutest, most spontaneous thing ever, or the cringiest, most awkward interaction of all time. Decide for you self after the new Second Date Update!See omnystudio.com/listener for privacy information.

Ugh, we're so done with New Year, New You. This year, it's more you on Bumble. More of you shamelessly sending playlists, especially that one filled with show tunes. More of you finding Geminis because you know you always like them. More of you dating with intention because you know what you want. And you know what? We love that for you. Someone else will too.

Be more you this year and find them on Bumble. Welcome to the You vs. You podcast. I'm Lex Barrero, inviting you to go beyond the titles and the accolades of the world's most successful entertainers. Each week, we take off the cape and get real about the inner battles, childhood stories, and the moments that shaped our guests. get real about the inner battles, childhood stories, and the moments that shaped our guests. Get inspired to become the best version of you. Listen to You vs. You podcast on the iHeartRadio app or wherever you get your podcasts. Camp Shane, one of America's longest running weight loss camps for kids, promised extraordinary results. But there were some dark truths behind Camp Shane's facade of happy, transformed children.

Nothing about that camp was right. It was really actually like a horror movie. Enter Camp Shame, an eight-part series examining the rise and fall of Camp Shane and the culture that fueled its decades-long success. You can listen to all episodes of Camp Shame one week early and totally ad free on iHeart True Crime Plus. So don't wait. Head to Apple Podcasts and subscribe today.

I'm Andrea Gunning, host of the podcast Betrayal. Police Lieutenant Joel Kern used his badge to fool everyone. Most of all, his wife, Caroline. He texted, I've ruined our lives. You're going to want to divorce me. How far would he go to cover up what he'd done? The fact that you lied is absolutely horrific. And quite frankly, I question how many other women are out there that may bring forward

allegations in the future. Listen to Betrayal on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. Have you ever thought about going voiceover? I'm Hope Woodard, a comedian, creator, and seeker of male validation. I'm also the girl behind voiceover, the movement that exploded in 2024. You might hear that term and think it's about celibacy, but to me, VoiceOver is about understanding yourself outside of sex and relationships. It's flexible, it's customizable, and it's a personal process.

Singleness is not a waiting room. You are actually at the party right now. Let me hear it. Yes. Listen to voiceover on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. Hey, we got a brand new second date for you today. Welcome to the podcast. It's Brooke and Jeffrey in the morning.

And today we got either romantic or a cringey first kiss story. I feel like we're very NPR right now. Yes, we are. I don't know. I like your vibe right now, bro. I'm just feeling, honestly, I'm kind of overly emotional today because my daughter's done with fifth grade today. Oh, the tears. I know, that's an aside.

She's going to move and never see you again. She doesn't move after fifth grade. Yeah. Mommy's going to live with her in the dorms. Oh, no. Yeah, she's going to be the coolest girl. Oh, no. Sorry, I didn't mean to be so NPR. All right, what about comments?

What do we got? Yes, Zane said I, 31 years old, showed one of your podcasts to my co-worker, 67, and he absolutely loved it. But then he heard one where they didn't get back together at the end. And now I have to pre-listen to them before showing him because I'm not allowed to show him the sad one. Oh, that's kind of adorable. I like that the 67-year-old believes in love still. I don't know that the success rate is as high as he's going to hope it was. I don't want to laugh through this whole thing

and have him be sad at the end. They better finish fun. They're usually just mad at each other at the end. I don't know if it's sad. But they're all funny, so let's get them to cope a little more. Yeah, yeah. All right.

See how today's goes. It's going to start right now. Second date update. Brooke, I want you to think about the best date that you've ever been on. Oh, that's cute. I know it's probably not with your husband. No, it is with my husband, Jeffrey.

Nobody here expected it would be. But what's the thing that happened that made you say, Know it's probably not with your husband What's the thing that happened that made you say this date tops them all It's just the person I'm with Talking about yourself again the fireworks are like the the chef made me a $700 snail the three-way kiss at the end that's it that's what it was with the waiter okay yeah that makes sense well one of our listeners emailed the show saying his most recent date easily ranks number one all time and I'm just assuming he's been on more than one otherwise that statement really doesn't say much.

So let's talk to Chris about it. Chris, welcome to the show, man. How you doing? Hey, guys. Thanks for taking my call. I really appreciate it. Yeah, it sounds like you're putting a lot of pressure on this first date. Yeah, you have been on more than one date in your life, right?

Yes. No, I've been on a lot of dates in the last few years, and honestly, none of them really hit at all. Like, I didn't feel like there was any connection but this last girl Kendra it was like the date of a lifetime. Okay so are you saying that because of Kendra or because of the activity and the environment? I think it was a combination of the entire the entire night was kind of great you'll

see by the end. Okay our dating lives will look paltry in comparison oh yeah yeah yeah yeah let's get right into it tell us where'd you meet Kendra okay so I bought her flowers we went to a restaurant question that I asked her you're really eager to tell us and I appreciate that but where did you

meet her oh we met online. I don't even know where he bothered asking that. I understand why that was a confusing question. Yeah, I see. Now where did you two meet? At a restaurant, it sounds like. We met at a restaurant. I'm glad you let him.

And he bought her flowers. And I bought her flowers, which is an important part of the story because she was so shocked by the guy because no guys buy flowers anymore That's what she said at me at least oh Well, they are pretty expensive That is a good point Alexis, I mean what did Kendra do with the flowers after you gave them to her? Well, that was part of the story the server even complimented the flowers When the server complimented the flowers she offered to let the server put flowers on everyone's tables

So she accepted your gift and immediately gave it away Which when you say it like that it doesn't sound so good It was really nice to watch that happen and I see other people happy with these flowers. It was a really nice moment It is a really good move though I feel like it looks good in her eyes and I assume it must have led to some good conversation to some good moments. It really did. In fact, I'd say it got a little cheesy and so good that I got myself a little vulnerable. If you know what I mean. Oh, the pants came off that quickly. Did you say I cried? Is that what you just said? I didn't cry, but I'm sort of as a 26 year old I gave up on meeting anybody at this point. So 26 isn't that old just so you know

She's 29 and she said she was going through similar stuff so it was like we kind of hit on the same subject What happened at the end of the night we went back to her place we walked to her place She doesn't live that far from the restaurant. So it was really nice romantic walk We held pinkies That's the friend finger That's the one you do pinky promises with your friends Anyway, did you uh after the pinky holding did you get a kiss? So it was kind of a funny situation

She lives in a community that has a wall around it and you have to it's not easy to get into you know A prison of some sort? I think it's just an apartment with a gate is what he means Which are pretty common. Okay. I like bio prison. I'm not familiar. Okay, I get it There's a gate so there's a gate and she didn't have her key You're locked out or maybe it's a move that she's pulling where she's like, oh, I can't find my keys Oh, she was what happened. Oh, yeah. Do you need me to strip search myself? Maybe I was more like maybe we should go back to your place So what happened Chris so I know this sounds ridiculous, but so I decided to jump the gate. Oh, so you

can open it on the other side. She have like a window. Right. Oh, you can open the gate. Yeah. Yeah. Yeah. Yeah. Yeah. I had to climb it and pull myself up over it. As I'm pulling myself up over it, I get stuck. My pants get stuck on it. I'm hanging upside down Right Yes, Brooke What did she do? Well, she kissed me Upside down

I was just as shocked as you were Wow I guess she likes her men immobile, vulnerable Now I can get them, now I can pounce Did you like it? Like was that awkward or was it romantic? Oh no it was a nice it's a very nice romantic moment but it's been a couple of days since that happened we texted for a couple of days and then since

then she hasn't gotten back to me Maybe you're a bad upside down kisser. Yeah, it can be confusing because usually you put your tongue this way but when you're upside down it needs to go that way. She found another man suspended on a fence and took down his desk. Maybe that's her thing. Some guy working on the phone lines. Okay, well we're gonna come back, we'll call Kendra for you and try to get you your next most romantic date ever when we get you a second date.

Maybe a right side up kiss? Let's not get crazy. No, we're good. We'll do it with your second date update next. Second Date Update If you're just joining us, we've basically got the real life Peter Parker on the phone. Oh. Who received the rare coveted upside down kiss during his date with Kendra. You didn't see the sequel where Spider-Man got his pants cut?

I just feel like Tom Holland's a little hotter. He doesn't. That's OK. Yeah, we're still in the Tobey Maguire universe with this one. Yeah, Tobey would totally get his pants stuck on a fence. Yeah, because it happened after Chris fell the wire universe with this one. That was that iconic one. Toby would totally get his pants stuck on a fence. Yeah, absolutely. It happened after Chris fell while scaling the security gate outside of Kendra's apartment,

as you do on a lot of dates. Yeah, those fences are hard to climb, though. Yeah. Honestly. Pants got caught when he fell, and it was there in that embarrassing moment when animal instinct took over. And Kendra walked right up to him and smooched him in the face.

Which is such a good sign because that really could have been an ick moment for her. Yeah. You know? And obviously she thought it was adorable. So no wonder Chris is describing it as his best date ever, but weird that she's not texting him back since she's the one who initiated that moment. You know what? Yeah. We never asked Chris, did she ever

get back into her apartment? She locked herself. Because maybe that's why she hasn't responded. That's a good point. Yeah, somebody came by a few minutes later and let her in. Oh. Oh, OK. OK, that's good.

You guys didn't even wait that long? I didn't even think about just waiting till somebody else showed up. Oh, yeah. That would have been smart. We're going to call Kendra. We'll see if she picks up. Oh, god, I hope this works out for you. call Kendra, we'll see if she picks up.

God, I hope this works out for you. I mean, there's so much pressure on this one. Yeah. You know, it's like his best date he's ever been on. Well, I felt pretty relaxed until you said that. Now all of a sudden I'm super stressed out for no reason. Don't screw it up, Jeff. Oh God, okay.

Here we go then. Hello? Hey, is this Kendra? Who is this? I think that's a yes. She said, who is this? Oh, that she said seriously? No, she said, who is this? Sorry, Kendra. Hi, Kendra. We're a radio show. We're called Brooke and Jeffrey in the morning. How many of you are there?

Too many, yes. I agree. I'm sorry. I'm sorry. I'm sorry. I'm sorry. I'm sorry. I'm sorry.

I'm sorry. I'm sorry. I'm sorry. I'm sorry. I'm sorry. I'm sorry. I'm sorry. I this? Sorry, Kendra. Hi, Kendra. We're a radio show. We're called Broken Jeffrey in the morning. How many of you are there? Too many.

Yes. I agree. It's a whole show, Kendra. Okay. All right. Yeah. So we're reaching out to you because one of our listeners has asked us to get a hold of you, a guy that you went on a date with recently named Chris.

Oh okay. Yeah. Yeah. So this is all part of a segment we do called a second date update where we're trying to figure out if there's a reason you have stopped texting him after the date. Um I mean obviously obviously, yeah. Obviously not to him. The reason should be obvious. No, no, no. Just like it's obvious that yes, I have a reason. Yeah. OK. We just want to know because we spoke to Chris and he told us about your date and it sounded actually much better than we ever thought.

It could have been given the circumstances Honestly, I'd love to hear your side of the story. Yeah, okay It was a good day. Like it was a really good date. Honestly, okay I mean, I wouldn't have kissed him at the end of it if it was a bad date. Oh my god That's where you and Brooke differ That's where you and Brooke differ. So that's nice to you. Brooke kisses everybody. She's mad at you.

You better watch out. No, but he told us about that first kiss. Like that was crazy. The upside down one? Yeah. I mean, when you have a movie moment, you have to like take it, right? Oh, you felt like it was that magical too. Like it really was a movie moment.

Well, yeah, it was a Spider-Man kiss. Totally. Yeah. That's the first thing we jumped to as well. Well, if that's the case, then why after your movie moment aren't you calling Chris back? Well, I mean, I don't really know what he told you besides that we kissed. That was kind of the answer. I mean, that was the majority. We know that you guys went to a restaurant. He told us about the flowers, that he brought you flowers and you guys passed

him out among the other tables. He immediately gave his gift away. Oh, yes. I didn't think he would mind. No, he thought it was really sweet. Oh, OK. OK. OK. Yeah. Here's the thing. Chris is great, but he lied to me and I mean he lied about something pretty big and I- Pretty big? Uh oh.

Like what, like his name or something? Dude, I mean- No, it's not his name. He said that he was 26 and he's like 42 ish. What? Oh, that's a big stretch. Wait, wait a second, wait a second. Wait a second.

You had a good time. I had a good time. Why does it matter what age anybody is? Okay, okay. Wait, wait, wait, wait, Chris. That doesn't sound good. Yeah, Kendra, you didn't know this, but Chris has been listening on the other line. Maybe with an earring age.

Yeah. Oh my God. What? That's because I'm 42. Look, that's off. Wait, you, hold on. You are 42, Chris. That's true. You told us that you were 26. Yeah, what's up because I'm 42 look at all You are 42 Chris you told us that you were 26. Yeah, I'm kidding bro, but age doesn't matter It doesn't matter how old I am again. We had a good Why do you lie

That's only 13 years difference And Chris if age isn't important, then why did you lie about it? Because she wouldn't have gone out with me if I said I was 42. I had to tell her that. Of course. When I was in my twenties, I wouldn't date somebody in their forties either. Yeah. It happens in Hollywood all the time. Men and women are older than the significant others. Actually's super true. A lot of healthy relationships in Hollywood. And it's people having the information to make that choice, right?

So she, you lied to her. Yeah. Kendra, what are your thoughts on this? I mean, here's the thing. I'm not entirely true to my age on the apps either. What? I say that I'm 29, but I'm actually 31. But that's not like a big deal.

Wait a second, wait a second. You lie about your age online. That's disgusting. Well, girls I'm actually 31. But that's not like I'm- Wait a second, wait a second. You lie about your age online? That's disgusting. Well, girls are allowed to lie. Wait. Okay, now you're being sarcastic. You don't really have a leg to stand on when you're doing it. I think he's being sarcastic.

You're being sarcastic, right, Chris? No, it's the same. A lie is a lie, whether it's 29 or 42. Okay. So you're not upset that she lied about her age because you lied about yours? I'm upset that she's upset that she lied about her age because you lied about yours I'm upset that she's upset about me lying about my age if she lies about her The lies should cancel out and you should be on even playing field

No, here's my thing it's like when people are like looking for people who they want to date and they go to my age bracket They're looking for people between 30 and 40 and I don't want the people like I'd rather use someone who's a little bit younger So you aged out of the age bracket you're interested in is the problem Yes, but not by 16 years Problem yes, but not by 16 years He doesn't know how to do math it's literally 16, but he's doing the same exact thing that you're doing He's lying about his age to open up his options the same way that you are But he's opening it too far. Yeah Okay, I mean I can't I don't think what she's doing is right But I can see her point like you have a generation gap between somebody

Well, I guess you're 31 now. So now you're only 11 years apart in age. So now it's not as Billions of years old. What's the difference between 13 years? I can't tell whose side I'm on Yeah, and technically the age gap is just 11 years now Yeah, that's right. I wasn't listening to you Brooke cuz you're older I have my cut off at age 35. So it's so down Alexis if you have anything to say feel free to jump in. I'm so confused. My question is when you kissed him did you know he was 40 by then I had.

This and I mean I knew he wasn't 26 but that means you guys got along so well even you were bending your rules a little in right exactly I wasn't bending my rules 11 years No, you're right. You are right, but I'm just saying okay point you came to a conclusion almost and you still I think Jose's On to something you both can you get over this is that that's really the question Is that the only problem because if you guys just get along great? Just a big lie about who you are, is that it? Well, there is the saying that age is just a number.

It shouldn't matter if the connection is real. And if that connection is true, we'd like to offer to send you two out on another date, and we would pay for it. Oh, that would be nice. I like when people pay for my dates. I'd do it. I'm down. Oh, he's older. He likes my food.

He's a cheap, cheap old man, I see. Waiting for that senior discount. But Kendra, we will pay for it. It's up to you. Look, if we would have met organically and had the connection we had, then I might have been able to forgive that he's 42. But the lying is it's just gonna bother me.

But your lies don't bother I'm sorry, man His entire life well if that's it guys, I'm to let her know the truth that I'm not actually 42. I'm 46. What? No. What a 20-year lie. No, you're not.

Oh my God, is that why you wore the baseball hat backwards on our date? Like, you're literally a dad. No, that's why you couldn't get over the fence. No wonder he knows who Tobey Maguire is. Tell him. Brooke and Jeffrey in the morning. Welcome to the You vs. You podcast. I'm Lex Borrero and every week we sit down with some of the biggest names in entertainment

to talk about the real stuff. The struggles, the doubts, and the breakthroughs that made them who they are. We go deep, throwing childhood trauma, family, overcoming loss, and the moments that shaped their journey. These honest conversations are meant to take the cape off loss, and the moments that shape their journey. These honest conversations are meant to take the cape off our heroes, with the hope that their humanity inspires you to become a better you,

and therefore set you free to live the life of your dreams. Here's a sneak peek. I'm trained to go compete. I'm trained to be like harder, but sometimes that mentality stops you from stopping and smelling the flowers in your own garden. Is it wrong to want more? We migrated, our family migrated here.

I'm like second generation. Who's not going to have a trauma coming from a foreign country and you arrive in the United States and you don't speak English? Listen to You Versus You as part of My Kultura Podcast Network, available on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Camp Shane, one of America's longest running weight loss camps for kids, promised extraordinary results. Campers who began the summer in heavy bodies were often unrecognizable when they left.

In a society obsessed with being thin, it seemed like a miracle solution. But behind Camp Shane's facade of happy transformed children was a dark underworld of sinister secrets Kids were being pushed to their physical and emotional limits as the family that owned Shane turned a blind eye Nothing about that camp was right. It was really actually like a horror movie in this eight episode series we're unpacking and investigating stories of mistreatment and re-examining the culture of fat phobia that enabled a flawed system to continue for so long.

You can listen to all episodes of Camp Shame one week early and totally ad free on iHeart True Crime Plus. So don't wait, head to Apple podcasts and subscribe today. Man, I know this happens all the time on the dating apps now where people lie about their age, but I don't know if I'm ever going to understand the thinking behind it. Because at some point, the truth about your real age is going to come out. Yeah. Well, duh, yeah.

Maybe it's like one of those things where you feel like you'll just be so connected by then, it won't matter. Yeah. Like that's what you hope, right? I mean, maybe it's like one of those things where you feel like you'll just be so connected by then, it won't matter. Yeah. Like, that's what you hope, right? I don't think that that's ever true. A lie always matters, but... Yeah.

Because eventually, you're gonna have to explain why your high school graduation photo has a watermark that says Sears Portrait Studio, 1986. And then everyone's gonna be confused. I thought it was bold that he tried to play off that he was younger than her. Yeah. Not just like, hey, I'm to play off that he was younger than her. Yeah. Not just like, hey, I'm 32 or like I'm a few years older. He's three years younger than her?

He's like overcompensating. All I need to know, 20 years different. All I need to know is what filter he's using on his photos. Oh, that's good. I mean, I don't need it for personal use, I swear. It's just a curiosity. Exactly. That's gotta be it.

Okay, so just to be clear, we're not saying don't lie we're just saying lie smarter. Yeah, okay We're gonna do that Jeff. We're saying don't lie. I'll make it believable Okay If you want some help with your dating life lies or not email the show We'll call that person who's not calling you back and go find out all of our second dates They're up online wherever you get your podcast to search Brooke and Jeffrey. Welcome to the U versus you podcast. I'm Lex Burrero, inviting you to go beyond the titles and the accolades of the world's most

successful entertainers. Each week, we take off the Cape and get real about the inner battles, childhood stories, and the moments that shaped our guests. Get inspired to become the best version of you. Listen to You Versus You podcast on the iHeartRadio app or wherever you get your podcasts. Camp Shane, one of America's longest running weight loss camps for kids, promised extraordinary results. But there were some dark truths behind Camp Shane's facade of happy,

transformed children. Nothing about that camp was right. It was really actually like a horror movie. Enter Camp Shame, an eight-part series examining the rise and fall of Camp Shane and the culture that fueled its decades-long success. You can listen to all episodes of Camp Shame one week early and totally ad-free onHeartTrueCrimePlus. So don't wait. Head to Apple Podcasts and subscribe today. I'm Andrea Gunning, host of the podcast Betrayal.

Police Lieutenant Joel Kern used his badge to fool everyone. Most of all, his wife, Caroline. He texted, I've ruined our lives. You're going to want to divorce me. How far would he go to cover up what he'd done? The fact that you lied is absolutely horrific. And quite frankly, I question how many other women are out there that may bring forward allegations in the future. Listen to Betrayal on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. Have you ever thought about going voiceover?

I'm Hope Woodard, a comedian, creator, and seeker of male validation. I'm also the girl behind voiceover, the movement that exploded in 2024. You might hear that term and think it's about celibacy, but to me, voiceover is about understanding yourself outside of sex and relationships. It's flexible, it's customizable, and it's a personal process. Singleness is not a waiting room. You are actually at the party right now. Let me hear it. Listen to voiceover on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. A lot of times big economic forces show up in our lives in small ways. Four days a week, I would buy two cups of banana pudding, but the price has gone up. So now I only buy one.

Small but important ways. From tech billionaires to the bond market to, yeah, banana pudding. If it's happening in business, our new podcast is on it. I'm Max Chaston. And I'm Stacey Vanek-Smith. So listen to everybody's business on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.