Brooke and Jeffrey: Second Date Update - Second Date Update Classics: Date Night Detour + Barista Foam Job

Episode Date: November 22, 2025

Part 1  If you asked a million people if they thought the surprise one of our listeners had for the woman he was dating was a good idea, NOBODY would say “YES!” Part 2 One of our listeners is a barista and says she did something she would NEVER normally do… but taking that risk got her a date with a hot customer and now she wants our assistance bringing him back one more time!See omnystudio.com/listener for privacy information.

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Enter now at iHeartpodcastawards.com. What do you get when you mix 1950s Hollywood, a Cuban musician with a dream, and one of the most iconic it comes of all time? You get Desi Arness. On the podcast starring Desi Arnaz and Wilmer Valderrama, I'll take you in a journey to Desi's life, how he redefined American television

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The to-do list is so long on a Saturday before Thanksgiving. Oh, man. We're here for you, just so you know, it's Brooke and Jeffrey, and we've got two back-to-back classics for you. So you can just get done whatever you need to get done and not think too hard about it. Yeah. We love that. We hope you enjoy it, and we love to start with a comment from one of our listeners. Yes, actually, it's from one of our show friends, Jamie Glassman.

And Jamie the artist Yes, so Jamie has drawn and painted us multiple different characters and portraits and Jamie, if you're listening, your fairy god The Fairly Odd Parents. The Fairly Odd Parents drawing of me is still my Discord. It's still the Giggle Gang official poster.

I have one of her drawings up in my office right now. Fairly Odd Parents is top one. Yeah, yeah. It's so good. It's really cute. But anyways, sorry, not just to talk about Jamie. We love you. We love you. did comment and said, I've been listening for almost 10 years and I've converted my dad and I'm trying to convert my sister. Oh, you can do it, Jamie.

We believe in you. Just turn it on in the background whenever you're around them. Yeah, exactly. All right, hey, thanks for being here and for all the love, Jamie. And your back-to-back classics start right now. I always hear people say there's a lot of weirdos on the dating apps. Yeah? Yeah.

Well, guess what? After today's call, you're going to think there's a lot of weirdos and realize. life to. Yay. Wait, I think they already do that if they listen to the show. That's for sure. I say that because of the last second surprise that one of our listeners had for the woman that he went out with.

And if you asked a million people, not one would say, yeah, I think that's a good, well-thought-out idea. You should totally go through with that. You're going to hear it in your second date update coming up right after this. Second Date Update. Where's the worst place to take? a woman on a first date. The worst? Oh my gosh.

Brooke and Jeffrey in the morning, home of the second date update. Like a garbage dump? Are you going to give us options? Because I have some ideas. Yeah. I mean, crematorium comes to mind. Oh, that's even worse than the garbage dump I was saying.

Especially if you talked about having barbecue already that night. Oh, gosh. Come on. It's just a smoky flavor is always good. Yeah. But there is something that might be worse than that.

There's no way, Jeff. Well, I was going to say Chernobyl, but you know what? Okay. Let's talk to our listener, Rhett, because he thinks he may have taken his date someplace pretty regrettable. Oh, no. It's not going to sound that bad now. I mean, that's all you have to do is come on our show and you'll feel better by comparison. Yeah, right.

Before we find out about this woman, just tell us the place that you took her. Yeah, I took her to my ex's house. Oh, God. What? What? I have so many questions. Yeah, we got to back up here. Not even like the restaurant where my ex works.

Yeah. Yeah, yeah. I know it's a bad idea now. Okay. It's good that you realize that. But let's go back and start from the beginning. Where did you meet this woman and what's her name? And not your ex.

Not your ex. The one you actually took out. The girl that I took out, her name's Christina. We met at a hiking club. Just a small group of people that get together and take hikes on the weekend. Let me guess you reached for the same cashew in the bag of trail mix and your eyes locked. Aw, that's cute. Like cashews, too.

You want this raisin? Yeah. How did you turn it from hiking to a date? Yeah. We're both cat people, so that's kind of how we came together a little bit on that. Okay. Okay. Bonded over cats.

Hiking and cat people. A lot of time to talk on heights. Yeah, that's true. So, I mean, you guys had a pretty good relationship then, probably before you actually moved into the romantic world, right? Yeah, I mean, we had tons of talks, and I mean, I showed her tons of pictures. My cat's name is Sorbet. So I set up a date at my house to help meet my cat. Okay, I like how you said your house.

That's good. Yes, we were going to make pizzas at my place. I got a fancy pizza oven. Nice. So we wanted to do that. Introduced her to the cat. She looked real nice. We didn't burn anything.

That's usually a good sign. I mean, were you able to have, because you guys had been friends already, were you able to have like some flirty moments? Like come up behind her and need the pizza, like show her, like grab her hands and show her, show her out of toss it. Yeah, we had like a little ghost moment with the pizza dough. Do not say you did that.

I'm just kidding. Yeah, it was still flirty, a little flower getting everywhere, but nothing crazy. Okay. All right, that's cute. I mean, it sounds like a setup to a great evening. Yeah, it sounds like a great setup to go over to your ex's house because how does that come into the picture?

So, I mean, I kept calling for the cat. The cat likes to hide when new people are there, so I figured they needed a little bit of time to get used to her. Right. I mean, cats notoriously don't come when you call them. Yeah. You know? Right.

And then I remembered that I actually had dropped the cat off at the cat moms that morning. What? No way. You remembered? You and your ex split custody of your cat? Yeah, yeah. I mean, it was kind of a contentious part of the breakup there. But, I mean, we're good now.

How could you forget that? It was the whole date, Senate. That makes you look so bad. You're a cat dad that doesn't remember where he left his cat. I had a pretty busy day, and it slipped my mind. I mean, I had other things to worry about. Okay. That is a lot to tackle, both pepperoni and cheese.

So I can understand. Your head was totally full. I still don't get... How did you end up at your ex's house? So right after we ate, I was pretty disappointed that she couldn't meet Sorbet. Yeah. Okay. Yeah, but just chalk it up and you make a plan for the next.

next time, right? Yeah, I wish I would have done that. That's a good point. On our way home, I just figured I'd swing by my exes and introduce her to Sorbet. No. We all made of taking her home. You brought Christina over to your ex's house. Oh, no.

It sounds really bad when you say it like that. And it is bad. You didn't warn either woman. So you're going to show up unexpectedly with a date on your ex's door and Christina doesn't even know that's where she's going. Yeah, but usually my ex is pretty cool. if I need to swing by and see the cat, you know? Oh, yeah.

Alone, probably. Yeah, how did that go? So, I mean, when we showed up, it was fine, but I could kind of tell that she wasn't really digging it, and X wasn't really happy that we showed up to see the cat. Yeah. Really? Yeah, shocking.

I can see why you guys broke up. She's not an not accepting woman. Yeah, that's it. Yeah, it was a lot of silence and petting the cat on the couch, And it was real awkward. She was just staring at my date the whole time. You were all sitting on the couch together. Why did I imagine this just at a doorstep?

You know what I mean? Like, say hi to the cat, then everybody parts. It's like a scene to a funny movie. You're inside. Okay, so you guys all spent the night at your ex's house. And then when you left the next morning, how did that go? That didn't happen, thank God. Okay, good.

The whole time ended in like a real big fight. Oh, my God. A fight with who? You and the ex or what? You and the cat? Everybody kind of ended up shouting. Yeah, Christina didn't like that my ex was being rude. My ex didn't like that I brought a girl there.

It was a whole thing. What? Okay. Why are you wanting to call this girl again? Christina doesn't want to have anything to do with you. Yeah, but your show says you help people get second dates. Doesn't say we do the impossible. Yeah, we're not miracle workers over here, but.

Oh, my gosh. Can I just ask when you drop Christina off at her door, what was the last thing she said to you? She actually gave me the finger, but I don't think she meant it. If it's a finger that I'm thinking of, then it could be a good thing. She just was the wrong finger. She was trying to go for the ring. I was a little bit she didn't Uber. She still took the right and then flipped you off.

Wow. She was emotional. Now that we've had some space, it's been about a week or so. So I figured we could give it another shot and you guys could help me out. Guys, at least this will be a great story, right? Yeah, I'm very eager to hear how Christina felt the experience went. This woman's going to be cussing. We don't know.

We're going to call her. We'll see how she's doing. But we do your second date update right after this. Second date update. What went wrong on Rhett's first date? Gosh. A little hard to say. Who knows, Jeff?

Because there was pizza. Oh, that's good. There was cute cats. And the one tiny mistake. And when I say tiny, I mean like minuscule. There was kind of a fight at his ex's house that involved him, his, date and his ex-girlfriend, resulting at the end in a certain finger being pointed at Rhett when he dropped Christina off at home.

It wasn't a-proposal with the wedding ring. It wasn't the index finger. Other than that, though, A-plus date. Really? Rett, you would agree, right? Yeah, other than all of that, I guess it was fine. Other than that date? The date was good.

Okay. Okay. Wait, I have a question. Have you had a chance to apologize to Christina? Well, and that's the biggest thing is I just haven't. seen her in the hiking group at all. And it's not often you get to go from friends into dating. So I just, I didn't want to mess that up.

Oh, yeah. Yeah. And I don't necessarily. You didn't, I'm sure. I don't necessarily think you're the one who needs to apologize. It sounds like your ex-girlfriend owes her more of an apology for not being cool about this. No, he needs to apologize to both women, Jeffrey. We don't know what started the fight.

You can't bring a date to your ex's house, especially unannounced. I don't know. What? Who does that? I'm just clearly read as somebody that wants everybody to get along feels like you should be able to move past ex-grievances. The ladies, I don't know why you guys are holding on to this like it's a big deal. I hope your ex shows up at your house today, Jeff. I don't have one. That's true.

Jokes on you. All right. But we don't know the whole story. We have a hunch of what went wrong. We need to get Christina's angle to really understand the full scope of this. I can't wait to hear her story. And the thing is, is that you actually sound like a really nice guy that just made. dumb choices.

Yeah, I'm just a really nice guy who made one dumb choice, and I told you the whole story. Okay. Yeah, but her perspective is going to be interesting. Yeah, perspective. Well, let's find out what that is. I'm going to dial her right now. Hopefully, she has nothing but good things to say about you. Or she doesn't just cuss at us and hang up.

Okay. We'll see how this goes. I'm dialing her. What if she flips us off as she answers the phone. We'll be able to see it. We'll be able to feel it, though. Here we go. Hello? Hey, is this Christina? Yeah. Hey, Christina.

Hi, good morning. We've all been very eager to talk to you. We're a radio show called Brooke and Jeffrey in the morning. And I don't even know where to begin, honestly. Hi, Christina. How are you doing? Fine. What is this?

Confusing. Yeah. This is a radio show. And we're doing a segment trying to help out one of our listeners. that you went on a date with recently. His name is Rhett. Uh, what? Yeah.

Yeah. I mean, actually, that's a better response than I expected from you, to be honest. Yeah. I'm being serious. Because we heard about your guys' hangout. We won't rehash the whole story. Wait a second.

Red called you? Yeah. Yeah. You emailed us. Why is he doing that? Well, obviously, because he likes you. Yeah, he wants a date. Well, I mean, it's not just that.

Like, you guys were friends in the hiking group, and then you had one date and he knows he screwed it up. Yeah. Can I just hear the story? Like, I want to hear from your perspective. Like, you show up to his ex's house. Did you know that's where you were going?

No, he was like, oh, I've got something to show you. I really want you to see that. Oh, I've fallen for that line before. We all have jazz. Yeah. Okay. I mean, at first, I just thought it was like his friend or something. I didn't realize it was his ex.

And then when we get into this argument, she called me a whore. Oh, God. Oh, what? Wait, I don't repeat it, but what? Wait, how do you go from Petty the Cat to that? She did some major insecurity issues or something because she was like, well, do you know what he likes? Because I know what he likes. Oh, God.

Okay. We did not know that part of the story. Yeah, like I said, she yelled at me and called me a wh-h- Wait, what did Rhett do while this was happening? She was yelling back at her. It was just, it was so dramatic. And this is a first date. Yeah.

Okay. I'm going to tell you on the third. 32nd date, that would not be okay. Look, I know that we all feel terrible about that. Rett feels sorry for even making the decision to bring you over there. Yeah. I mean, he honestly sounds like a nice

guy that made a dumb choice. I don't know. He lied to me, too. Okay. It's not just that. Like about bringing you over there to introduce you to his cat? No, before that. So I knew him from hiking. Like, we hiked together with like a group and we were talking about our cats and he told me

that Thorpe is five. and my cat is 5 too so I was like oh that's cool to the same age but then his ex told me that sorbet is 9 I don't know what my cat is either I think we should probably just come straight the argument with the ex and the name calling what

that's almost a five year difference that's crazy okay that was worse to you than the argument that broke out between the three honestly I think that he lied about his cat's age on purpose I think he was trying to say that it was the same image as my cat so that they would get along. I mean, we do hear a lot of people lying about their age on dating apps to impress somebody, not usually lying about their cat's age

to impress each other, but... Well, yeah, but like, that's important to me. I have something to say here. Oh, okay. You shut your mouth, you liar. I really hope you would, because we need to tell you, Christina, that Rhett's been on the other line listening to this call, wanting to clearly speak.

And hopefully apologize. Well, yeah, I mean, I'm going to apologize for, the fight, but not for my cat being a different age. I mean, those are just details. Well, you might not think that's important, but I do. I don't have kids and not planning on having kids

anytime soon. My cat is my world. Like, I don't want my cat to be the little second sidekick cat because you have this older, leader, mean cat. Well, maybe if your cat was more mature, it'd be okay hanging out with my older cat. Okay. My cat is

Plenty mature. Oh. It sounds like where's a top hat or something. I don't know what we're fighting about, really. I don't get it either. I thought we'd really be concentrating on the name calling in the ex's house here.

Well, that wasn't cool, but neither is lying about the age is your cat. Why would you do that? Why would you lie about anything like that? That is true. What if the ex is lying? Yeah. I don't even know.

I mean, my ex wasn't lying about that. He is nine. And then if that's the only thing standing in the way of this, I mean, we can always go get a five-year-old cat. Okay. There are a lot of cats that need adopted. Especially the older ones. I like the problem solving.

That's a positive. So my cat's a third wheel now. That's great. What? I am so confused at what you're upset at. Yeah, you find very interesting things important for your dating life. You got to think of it from my perspective. If this does work out and we're together,

now we've got two full-time cats and one part-time cat that we're shuffling back and forth between his ex. Who thinks I'm a whore? What? Oh, between the ex who thinks you're, yeah. I mean, I could see that part. But, I mean, it's nine. It's not like you're going to have to do it for many years. I'm just saying.

I take offense to that because my cat may be nine, but she looks seven at worst. Plus, we don't know how many lives it has left. You could have all nine left. We are really stuck on this. I know. She's very upset that she got cat catfished. Yeah. That's the big issue.

Well, she got fish cated. I think it's just catfish. It is. You did cat cat catfish me. Okay. We're going with the double cat. Right, you're very sorry, right? Tell her how sorry you are for doing that. Yeah, yeah. I mean, I'm very sorry for telling you the wrong age of my cat. And I mean, going forward, I swear I won't lie to you about something like that.

Something like that. Why would you add that? Why would you just say I swear I would not lie to you? About anything. Well, because that's like super important. I want her to know how important it is that I'm taking her her cat age very importantly. I won't lie at all. Okay. I mean, honestly, Christina, he is taking it into account, and I think a lot of people would not be so patient with that. Brooke is basically saying team ret, team ret. And so we would like to offer to send you out on another date with him, and we would pay for it. I don't know.

Two cats, three cats, one cat, no cat, whatever. Howver many cats you want or don't want on it. Go to a cat cafe. Yeah, and find a five-year-old one. Yeah. Perfect. Well, I doubt he wants to go out again with a whi. Hey, some guys like that, okay? I hate that one.

Rhett, what do you think? I mean, as long as the price is right, I guess we could do it. Okay, I know it's a joke. I'm kidding, right? I'm kidding. Obviously, I would love to have a second try at this. Yes, he went through all this effort to make this happen, and we're running out of time here. So what do you say? Christina, one more date with Rhett.

I need a yes or a no. Fine, yeah, whatever. It's a romantic fine. Are you down? She just said fine. Yeah, she's still emotional. She'll get over it. I'm okay with fine.

I'm sorry, but are we miracle workers? Because that is insane. Yes, we should take all the credit for this. You're right. Brooke and Jeffrey in the morning. A decade ago, I was on the trail of one of the country's most elusive serial killers. But it wasn't until 2023 when he was finally caught. The answers were there, hidden in plain sight.

So why did it take so long to catch him? I'm Josh Zeman. And this is Monster, hunting the Long Island serial killer, the investigation into the most notorious killer in New York, since the son of Sam, available now. Listen for free on the IHeart Radio app, Apple Podcasts, wherever you get your podcasts. Hey there, Dr. Jesse Mills here.

I'm the director of the men's clinic at UCLA Health. And I want to tell you about my new podcast called The Mailroom. And I'm Jordan, the show's producer. And like a lot of guys, I haven't been to the doctor in many years. I'll be asking the questions we probably should be asking, but aren't. Because guys usually don't go to the doctor unless a piece of their face is hanging off or they've broken a bone. Depends which bone. Well, that's true.

Every week, we're breaking down the unique world of men's health, from testosterone and fitness to diets and fertility and things that happen in the bedroom. You mean sleep? Yeah, something like that, Jordan. We'll talk science without the jargon and get you real answers to the stuff you actually wonder about. It's going to be fun, whether you're 20. 27, 97, or somewhere in between. Men's health is about more than six packs and supplements. It's about energy, confidence, and connection.

We don't just want you to live longer. We want you to live better. So check out the mailroom on the IHeart Radio app, Apple Podcasts, or wherever you get your favorite shows. You know what really makes me happy hearing someone regrettably agree to go out on a date again. Fine, Jeff. Fine. They're going to look back and listen to this on their wedding.

day right before Christina turns to to the pastor and is like, oh, fine, I do. Yeah, well, I'm pretty sure the ex is going to show up to that wedding. Yeah. I just hope the cats show up. Oh, a little bride. I don't think anybody's showing up.

I think he's going to host it at their house. No. At the ex's house. Yeah. Yeah. It's a good reminder that everybody that everybody values different things in their relationships. And for Christina, she values

honesty about your cat's real age. That's number one on the relationships. Like, you could have still been dating the ex. She's like, I don't care about that. A round number five is ex-name calling. There you go, yes. It still mattered to her, just not quite as high. Everyone's got different priorities.

And we know that now. So whatever is important to you, we will call that person who's not calling you back. Email the show so we can help and go check out all of our second day podcasts wherever you get yours at Brooke and Jeffrey. Brooke and Jeffrey in the morning. In today's call, one of our listeners is a barista and says she did something that normally she would never do while working. on the job. Uh-oh. Wouldn't you know it?

A cute guy was involved. Yeah. So she took a risk in the name of love. And now, well, she's not getting a call back. Uh-oh. I'm wondering when you hear this, all the baristas who are listening, would you ever do this with a customer that you found attractive? Text into 7-8-5-92.

Is it that naughty? You're going to hear what happened in your brand new second date update right after this. Second date update. You never know when or where you're going to meet the love of your life. Oh, Jeffrey, that's so nice. That's what they say. Like years ago, Brooke met a hunky traveling salesman named Roi. She told us this story many, many times on the show.

But just to recap for anybody who doesn't know, after one steamy night involving a diner at the edge of town, passion took over. And to this day, her husband. firmly believes that those children are really his. Oh, my God. Jeffrey, that's too far. It's a story that's as romantic as it is factually correct. That is not true at all. I have

only fallen truly madly, deeply in love with one man, and that is my husband. Oh, I thought you named one of the kids' middle names was Roy after the real father, too. Okay, so you love your husband, but you still married, Roy. No, I don't think she's saying any of that. She's full-blown denying this. It's just Michael.

Your love life fuses the hell out of me, Brooke. It is hard to keep up with. All I'm trying to say is that love can strike anywhere at any time. I think that's great. Even when you work as a barista at a coffee shop, like our listener Jacqueline does. So let's talk to her. Jacqueline, how you doing? I'm doing okay. How are you guys? Good. You sound a little, like, sad or something. Are you all right? Yeah, I just, I need your help, basically. Okay. I thought maybe Brooke's love story brought you to tears with Roy.

the salesman, but I don't know, maybe you got something else going on. Tell us about it. Well, like you said, I'm a barista at a coffee shop. And a couple weeks ago, it was, yeah, it's chill. I like it. That's exactly the attitude that Alexis had when she used to work. They're just like, yeah, it's okay. It's fine. Well, a couple weeks ago, it was kind of a slow time of day, and I ended up meeting this really nice customer, and he ordered a latte. and he stopped and complimented me on my foam art with your what art

foam art Oh like a latte art Yeah you can draw little pictures Did you put your phone number in the foam on the top Yeah That would have been clutch It actually looks hard to do that It is hard because I actually didn't do any foam art

Oh you didn't? Wait what? Why would he say that? I don't know maybe he was just trying to talk to me But he goes oh my God Like, is that a dog's face? It looks just like my dog, Kevin. Yeah, he's totally just like joking with you to get your talk to you.

Oh, yeah. I mean, I think he knew I wasn't trying to do latte art because he said I was the Picasso of latte art. He was a baccaso. It's abstract. That's not necessarily pretty art. It is just very cool. In his cubism face. Yeah, sure.

Did you get his name, by the way? His name is Kenny. The dog's name is Kevin after Kevin from the office. I mean, how did you parlay that into anything? Well, so he was being like really friendly and sweet and I mean, I know this is kind of unprofessional, but since I haven't had a lot of customers coming in, he asked if I would come sit with him a little bit. Really?

Yeah. That is like, I feel like that's bold. I don't know that I could ever think of a scenario where I would ask any waitstaff to come sit with me. Although you did go to a Starbucks and try to ask out the baristas recently, and they all said no. It's a good point. It could be a good gauge, though, because if it's a dead, empty coffee shop and she's like, oh, no, I can't, he would be like, oh, okay, I can see you can. She's working.

So here's my point. So she can say, oh, sorry, I'm working. She has an excuse. But if she says, yes, I'll sit with you. It's a huge sign that she's into. Because she's at work. The ball's in your court at this point, Jacqueline, what did you do? I said, yeah, sure, let me just, you know, let my manager know I'm going to take my break.

Oh, you took a break. Oh, you even did it like on the up and up. Yeah, you should have done an oncoming at a time. Wow. Was it worth it? How did it go? It was good. Like, we were laughing, getting to know each other.

He asked if I was single and normally whenever a customer asked me that, I lie. And I'm like, I'm married basically. Yeah, yeah, yeah. But I was honest. I told him, yeah, I'm single. So he asked me for my number, and after he left, like, even my co-workers were like, oh, my God, that was really cute. Oh, no. You're like, oh, my God.

That's awesome. Plus, you get an immediate gauge. No, you get, like, I would love if two of my girlfriends could always go on every date that I went on to, like, tell me whether or not it went well. Alexis, if Brooks says, oh, my God, that guy and you are really cute together. What are you thinking? I mean, it's just, could I get someone else's opinion also? But, Jack, and this is a coworker whose opinion. you actually respect?

Oh, Jeffrey! I'm just saying. Yeah. It's a totally different situation, man. Oh, my goodness. So, wait, what's happened since? Well, we texted back and forth for a little bit, but, like, our last text exchange we had was a few days ago,

and it was kind of weird. Uh-oh. So he messages me. Yeah. So, what's up with Glenn? Does he still have his motorcycle? Who? What?

I don't know who, I don't know a Glenn or anyone with a motorcycle. Oh. I wrote. ha ha what are you talking about and he said oh come on stop playing coy with like a smirky face emoji so i wrote is this a game and he never wrote back when i was like kind of awkward and i don't really i'm turned on by that conversation i don't know about the rest of you i'm with alexis if you put a smirky face that means that you're not upset yeah you just smirky face yeah were you guys talking about astronaut john glenn at any point during your conversation in the coffee shop

pretty sure he has a motorcycle Is he still alive? I'm trying to solve the mystery here who Glenn is. So we have no idea. Clearly Jacqueline doesn't know. We should probably just call him and try and see if he picks up and can give us some answers.

Yeah. I want to know who Glenn is. We will reach out to this guy, Kenny, and maybe to his dog, Kevin, and try and get you a second date update right after this, okay? Okay. All right, hold on.

Second date update. Today, we have a mystery we need to solve. Ooh, I love a good mystery. The mystery of Glenn and the motorcycle. Seriously. Who is that? Sounds like a children's book. I've been thinking about this off the air, and I have a theory.

Okay. Because who else is notorious for driving a motorcycle around? Roy, the traveling salesman. Glenn must be his son, cruising the highway, stealing women's heart. at night just like his daddy did back in the day. What are you talking about? Those boys are notorious.

Yes, I guess we've never done a double date, second date. Stop it, Jeff. So this is interesting. There's no Roy. Jacqueline, would you be up for doing a two-for along with Brooke and Roy if we can get Kenny to agree to this?

I'm not sure about that. You're a fan of our show. You can turn it down. I am also turning it down. And I'm also kind of pissed. get the old guy, Roy, and you get the young one, Glenn. I'm sure you guys can work at an arrangement where you

could swap halfway through the night. Anything goes with Roy. Okay, let's concentrate on, wait, what's the guy's name now? They're Glenn. Chris. No, it's Kenny. We've got to focus on Kenny with his dog, Kevin. Kenny is the one that she met when he walked into her coffee shop the other day, made

a comment about her foam art. So let's try and get that connection back. Because after that text about that weird text he sent about Glenn, this has to be just some misunderstanding that's happening. Yeah, I mean, it's so random. Maybe he accidentally texted the wrong person.

Oh, that's weird. Yeah, he could have been texting, yeah. And maybe he's embarrassed because he feels like he looked like an idiot. So, yeah. Let's give him a call and see what he has to say. Here we go. Hello. Hey, we're looking for Kenny.

This is Kenny Hey Kenny Nice to meet you We're a radio show Called Brooke and Jeffrey in the morning Hi What? Who is this?

Oh man It's your favorite radio show You're on the radio right now Why are you calling me? Great question Because we're doing something called A second date update where we try to help Our listeners work on their

Love connections with people that they meet out of the world And you were somebody's love connection recently, hopefully. Yeah. Well, it sounds like you had a nice connection anyway. It's a girl named Jacqueline. Okay. Remember, you went to a coffee shop and you kind of had a nice little conversation with a

barista there named Jacqueline and you made a comment about like her foam art? Yeah, maybe. You said it looked like your dog, Kevin. Yeah. I do that. I do that a lot, actually. Oh, no. Wait, what?

That's a line? Why? Oh, bro. I've done it a few times. I mean, it is really funny and unique. But even if you've done it a few times, like... Yeah, well, it's a few times, but, you know, it's been more like a few times this week. What?

Actually. Oh, bro, how often do you do this? Why do you drink that much coffee? And why? Like, why even ask her to sit with you? Why even ask if she's single if you... Well, he can't even remember who this is. I know, but it, but like, if...

he's doing this all the time, what's your intention? It's obviously not to, like, have a relationship. Well, I'm actually really involved with a social media challenge right now. What? Social media? What challenge? This might be part of it. What are you talking about? Wait, Jacqueline was part of it?

Jacqueline was a part of that, even though, you know, I don't know exactly who she was. I'm sorry to laugh. Okay, what, tell us what is this challenge that you're doing? It's a challenge to. help me be more social and improve my social skills with other people. I'm going to say, so far, talking to you, I'm not sure it's working. Yeah, I mean, you come off almost like a player, bro.

Not like a social. What is the challenge? I don't understand. Well, I have to meet and engage with 10 new people every day that I don't know. Oh. Okay. Okay. In the video, it says that

baristas are friendly and easy to talk to, so I tend to hit a lot of coffee shop. It is part of their garage. So you're going to a lot of coffee places, just striking up conversations, hoping to improve your own social skills. You're not trying to pick up women necessarily, just be a better talker.

Yeah. So she read that totally wrong. You know that. I mean, like, you guys were... You were too smooth. Yeah. But what did you think when she was texting you and who the hell is glenn?

Yeah, she said there was a message that you sent about someone named Glenn in his motorcycle. Do you know what that is? Yeah, that was actually meant for someone else if I did that, yeah. Ah, see, we thought that. I was talking to a lot of people at once. So are you single? Can I ask that? Yes, I'm single.

Are you, wait, are you interested in dating any of these strangers that you talk to? Or are you just looking for like a million new friends? because Brooke bought all of her friends on Instagram. So that would probably be an easier route to go. Just if I could throw out a recommendation there for you. I know someone who did, but that was not me. What's the goal here? Love or just friendship?

I can't say I'm not interested in love. I am interested in love, but I'm really engaged in this challenge that I'm doing. And I want to see it all the way through and I want to finish it. And it's taken up so much of my time that I haven't really had any. go out on dates at all. Oh, my God. What a misunderstanding. Okay, how long till you finish it? How much longer?

I got a little over three weeks left. Whoa. That's a lot. Wow. But good for you, man. Hopefully it is improving. I think you could like meet a waiter at the same time you're on a date with somebody maybe? No? Try to be hopeful here.

You know, like two birds, one stone type of situation. Brooke wants you to quit on your challenge, but I have a better idea. Let's try and keep improving on your social skills by reconnecting you with that barista, Jackson. Because she's on the other line right now wanting to talk to you. Oh, okay. Yeah, sorry, that's how this segment works.

Jacqueline, you there? Yeah, I'm here. Oh, Jacqueline, how are you feeling? I'm okay. A little disappointed. I'm super sorry that we got a misunderstanding going. I mean, I didn't mean to let it get to that point. Like I said, I'm just trying to work on my social skills and complete this challenge.

Yeah. Just hearing your voice, though, and thinking about it, it is taking me back some. Are you the lovely girl I talk to with the blonde curly hair? I'm a brunette. Oh, but it's like a light blonde shade of brunette. If it makes you feel any better, Jacqueline, Brooke has worked with people. here for years and can't remember their names are who they are. Yeah, by the way, I'm

Jose. Honestly. If I saw Jeffrey in a grocery store, I'd just walk right past it. No idea. I'd walk back to myself if I could. I'm not a big fan. Jeff would be hiding. I have to ask a question really quick. Oh, no? Okay, go ahead.

Do you really have a dog that's named Kevin, like Kevin from the office? Oh, yeah. Oh, please say it's real. Yeah, I do. We have a dog making. There was a long pause there before you get answered. I don't believe it, actually. Have the dog hold up a newspaper.

I need a picture. Yeah, wait a minute. Maybe it's just his social skills kicking in. That's true. That might have a part of it. But look, the whole reason that we do these calls is to try and set you up on another date. So we would offer to send you guys out one more time to another restaurant or maybe another coffee shop, and we would pay for it.

I mean, I think the thing is that you really need to think about here. I keep wanting to call you Kevin, Kenny, is the challenge worked. Like, you've made real connections. You have someone who wants to go further. I would say that's winning the challenge that you wouldn't even need to do the three weeks. Because you've already improved so much. Like, she wants to hang out with you. I mean, I'm glad it's, you all think it's improving my skills and everything.

But, yeah, I really want to see it through to the end. I'm not a quitter. That doesn't mean you have to say no to the date, though. Yeah, we'll still send you out with Jacqueline, though, after your challenge is done in three weeks. Well, that might be really nice. Okay. We got a might be nice. Is that, are you willing to wait for that?

Jacqueline? I mean, I still feel like the conversations we've had have been good. And even if it just ends up being a friend thing, I'd still like to go out in a couple weeks if you want to. Oh, my God. She just wants to be around you. I don't know what the vibe is, bro. All right. Well, I'm calling it.

This is a successful second date update. We're going to reconnect you too, okay? Okay, that sounds awesome. Awesome. Just sweet people. I like this. And by the way, Kenny, I just need to ask, do you possibly have a father named Roy?

Stop it, Jeffrey. Get up. Kenny. He's not. If you do, tell him to call in for a double date update. He'll know what it means. Please do the long palms. Brooke and Jeffrey in the morning.

A decade ago, I was on the trail of one of the country's most elusive serial killers, but it wasn't until 2023 when he was finally caught. The answers were there, hidden in plain sight. So why did it take so long to catch him? I'm Josh Zeman, and this is Monster, hunting the Long Island serial killer, the investigation into the most notorious killer in New York since the son of Sam, available now. Listen for free on the IHeart Radio app, Apple Podcasts, wherever you get your podcasts.

Hey there, Dr. Jesse Mills here. I'm the director of the men's clinic at UCLA Health, and I want to tell you about my new podcast called The Mailroom. And I'm Jordan, the show's producer. And like a lot of guys, I haven't been to the doctor in many years. I'll be asking the questions we probably should be asking, but aren't. Because guys usually don't go to the doctor unless a piece of their face is hanging off or they've broken a bone.

Depends which bone. Well, that's true. Every week, we're breaking down the unique world of men's health, from testosterone and fitness to diets and fertility, and things that happen in the bedroom. You mean sleep? Yeah, something like that, Jordan. We'll talk science without the jargon and get you real answers to the stuff you actually wonder about. It's going to be fun, whether you're 27, 97, or somewhere in between.

Men's health is about more than six packs and supplements. It's about energy, confidence, and connection. We don't just want you to live longer. We want you to live better. So check out the mailroom on the IHeart Radio app, Apple Podcasts, or wherever you get your favorite shows. Man, this is a great example of, you know, sometimes all you have to do in life is just step outside of your comfort zone, try something new, and then naturally love will just find its way in. I don't know if it's love, but or friendship or something, but yes, yeah, I agree with your sentiment. Like, I think this was so cute.

Yeah. You know, he was just trying to push himself out of his normal comfort zone. And he did a great job. Yeah. I mean, he has multiple people texting him. I'm guessing she's not the only one that thinks that he's flirting with her. Yeah, probably not. It's funny because he's not trying, which makes girls like guys when they don't try too hard.

But he's literally not trying. He just wants to talk to somebody and move on. So vicariously, girls are like, um, hello? Like playing hard to get? I mean, I swear, it works. Just push yourself out there into something you don't normally do. So, Jose, what do you think? Skydiving classes maybe?

Oh, my gosh. It worked for Kenny. Yeah, I don't think that that's what Kenny did. What if the instructor's hot? And you're attached to her front. Oh, great. My girlfriend is going to see me pee my pants on her front. She'd be like, oh, that's warm.

Well, whatever you want, we can help you out with your dating life. At least try to. You can email the show at Brooke and Jeffrey. We'll call that person who wasn't calling you back. A decade ago, I was on the trail of one of the country's most elusive serial killers. But it wasn't until 2023 when he was. finally caught. The answers were there hidden in plain sight. So why did it take so long to catch him? I'm Josh Zeman, and this is Monster, hunting the Long Island serial killer, the investigation

into the most notorious killer in New York, since the son of Sam, available now. Listen for free on the IHeart Radio app, Apple Podcasts, wherever you get your podcasts. I'm Robert Smith, and this is Jacob Goldstein, and we used to host a show called Planet Money. And now we're back making this new podcast called Business History about the best ideas and people and businesses in history and some of the worst people, horrible ideas, and destructive companies in the history of business. First episode, how Southwest Airlines use cheap seats and free whiskey to fight its way into the airline is. The most Texas story ever.

Listen to business history on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. What do you get when you mix 1950s Hollywood, a Cuban musician with a dream and one of the most iconic sitcoms of all time. You get Desi Arness. On the podcast starring Desi Arnaz and Wilmer Valderrama, I'll take you in a journey to Desi's life, how he redefined American television

and what that meant for all of us watching from the sidelines, waiting for a face like hours on screen. Listen to starring Desi Arnaz and Wilmer Valderrama on the IHeart Radio app, Apple Podcast, or wherever you get your podcast. Podcasters, it's time to get the recognition you deserve. The IHeart Podcast Awards are coming back in 2026. Got a mic?

Then you've got a shot. Every year we celebrate the most creative, compelling, and game-changing voices in podcasting. Is that you? Submit now at iHeartPodcastawards.com for a chance to be honored on the biggest stage in the industry. Deadline December 7th. This is your chance. Let's celebrate the power of podcasting and your place in it. Enter now at iHeartpodcastawards.com.

Hey there, Dr. Jesse Mills here. I'm the director of the men's clinic at UCLA, and I want to tell you about my new podcast called The Mail Room. And I'm Jordan, the show's producer. And like most guys, I haven't been to the doctor in way too long. I'll be asking the questions we probably should be asking, but aren't. Every week, we're breaking down the world of men's health from testosterone and fitness to diets and fertility.

We'll talk science without the jargon and get your real answers to the stuff you actually wonder about. So check out the Mailroom on the iHeart Radio app, Apple Podcasts or wherever you get your favorite shows.