Brooke and Jeffrey: Second Date Update - Second Date Update UPDATE: Does This Smell Like Ur Mom?

Episode Date: July 30, 2026

Denise and Caleb were on our show late last year and we got TONS of texts asking to follow up with them. We did and now they’re back to tell us all the romantic details that have happened since! It's a Second Date Update UPDATE!See omnystudio.com/listener for privacy information.

Hey, Portlandia fans. Carrie Brownstein and Fred Armisen here. The Dream of the 90s is alive in podcast form. We're launching Podlandia, AEO rewatch, our brand new podcast where we revisit every episode of Portlandia together, breaking down sketches, going deep on our iconic characters, and pulling back the curtain on how it all got made. And we'll also be joined by the people who helped bring it all to life. Guest stars, collaborators and friends, including director Jonathan Chrysall, the mayor himself, Kyle McLaughlin, legendary musician Amy Mann, and many more.

Kyle is going for it here. You fully improvised, not just words, but a song. Well, I thought you were all going to write a song. I remember you thinking that. Listen to Podlandia. A.O. Rewatch on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. What's up, fam? I'm sports journalist Ari Chambers. Hey, what's up y'all? It's your girl, Sam J.

And we're the host of Everyone Watches Women's Sports, a new podcast from Together and IHeart Women's Sports. We're breaking down the biggest headlines. Naomi Osaka. Shout-hows to you Naomi. The viral moments. I've been obsessed with Kishan Rock's boxing journey. She looks good.

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Every week, the news gets worse. The world gets crazier. And Yamanika is here to tell whoever's responsible, you're the problem. Do you know I just found out who Sidney Sweeney was? If he got a bunch of women, then I should have a bunch of men. Do better or do less, so I don't have to do so much. I'm Yamanika, and I'm out.

Listen to You're the Problem with Yamanika on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. I'm Nick Totoro. You probably know me from NYPD Blue, The Longest Yard, or Spike Lease Black Klansman. And on my new podcast, delivering happiness with Nick Tatoro, I deliver pizza to a new guest. I've shared a slice with everyone from Seth Rollins. What are you doing my belt? To Bill Burr. I don't think I've ever met somebody so exactly out of their mind as I am.

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tale Mary. It was like the Jaws shark. Didn't always work, came with its own problems. That's what made it great. The cast of obsession. On set, there was so much magic happening with each scene we were putting together. Deep dives into classics like 2001 of Space Odyssey or Fight Club. Plus weekly episodes on all industry news.

Listen to Raiders of the Lost podcast on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. And for more, follow at Raiders of the Lost Podcast. and at TikTok podcast network on TikTok. Welcome to your second date podcast. We got a brand new episode for you today. It is an update update. So we will play the original second date.

We understand that you may have heard this already. Uh-huh. I always have to establish it. Yes. And it's always missed. So don't worry. Yeah. But in part three,

we're going to have a couple back on the phone to see where the relationship is at since they've been on our show. Yes. So we'll play the original. Little ad. Skip, do whatever you want. Yeah. Then they're back.

Okay. That's exactly right. All right. And we're talking about yesterday's show in the comments. Am I right? The mom blocked second date update. Oh, the mom who suddenly surprise showed up. Yes.

And Natalie commented, I have a son and daughter who are both dating. I've learned to call all their dates, sweetie, and keep it moving. I will commit names to memory until I get a wedding invite. That's so good. That's so good. My mom at one point pulled me aside and said, Brooke, you don't have to bring them all home. Oh. I don't need to meet them all.

That's so funny. My mom's opposite is she won't know until I am getting married that I've been dating someone. Sorry, Barb. Oh, it's so good. All right. Here we go. Your update, update. Brand new starts right now.

If there's one message we've been promoting on these dating segments for years, it's ladies, get yourself a mama's boy. You will not be disappointed. Not too mama boy either, right? There's a line. There's a line. But a little passion, too. What? And that couldn't be more true than with today's call, which started when a young man approached a perfume

counter trying to find a special gift for his mother. And that turned into one of the more awkward and somehow weirdly adorable date situations we've ever had, which is why today the couple is back on to fill us in on what's happened since. That's right. It's a brand new second date update, update coming up right after this. Brooke and Jeffrey in the morning. Second date update. Big day on the show, because Denise is back.

Oh, I've been waiting for Denise. We all have. You may remember her from a second date update around six months ago or so, where her strategy was to find available men at the golf course. Oh, yes. Yeah, that was smart, too. She decided to take up the hobby, and she would go there and say, oh, no, I don't know how to do this.

How do I swing this long metal stick? And then weld to do you. gentleman would come over and help her. She ended up meeting one guy named Franklin, who owned a couple car washes. That whole thing didn't work out in the end. But Denise is not giving up. That's right, Denise. She is back requesting our help once again, but not hitting the golf clubs, apparently.

We got a new man hobby? According to your email, Denise, you've got a new strategy to meet guys? Yes. Okay. We're trying to hear it. Do tell. Okay. I was thinking about other places

that eligible single guys would be. And I realized that around the holidays, there's a lot of them around the perfume counter shopping for their moms and their sisters and their aunts. Their girlfriend. Why? Mostly, yeah. Jose said.

Just keep the list going there. Guys buy perfume for their moms? I've never bought for my mom. But I have bought my mom chocolate strawberries, so there's a line there. She should get some perfume next time, too. I was going to show her. Yeah.

Wait. Not too far-fetched, right? No, we actually are a little confused, Denise, because most men buying fragrance, they're going to have a significant other. Most. Most. Exactly. Or maybe he's helping his friend. Oh, we didn't think of that, Brooke.

You can't see the look on Brooke's face right now, but she is shaking her head very skeptical about this entire thing. It's a reach, but it sounds like it works for you because you're on with us, and you must have. met somebody this way, right? Yes. So I did get a part-time job at a department store. Oh, okay. I do have a full-time job, but I'm just doing this at night to meet guys. Oh, wow.

Wow, that sounds smart. So who'd you meet? Okay, so I did meet a guy. His name is Caleb. You know, what really caught my eye was that he was very shy compared to all of the guys that I've seen all day. And he was actually getting perfume for his mom. Oh. We found him.

Yeah. They exist. Okay. Oh, cute. But he didn't know what to get her. So that's where I came into play, luckily. Okay. And I took this opportunity to flirt with him, and I sprayed him on my hand and on my neck. Oh, you do the neck move?

You had him smell your neck? That's actually legit. Does this smell like your mom? Wow. You pulled out all the moves, okay. All of it. All of it. All of it.

All of it. All of it. He went to one of the perfumes. and I rung him up. And, you know, he just kind of stood there while hanging around the counter because, you know, he's so shy. And I was just initiating conversation. So I was very, very direct. And I said, if you want to ask me out, it's okay, you can.

Aw. That is awesome. I wish every girl would do that. We need a big green flag. Like, come on, buddy. No, because if they say no, then I'm going to go. Oh, my God. Never moved my house again.

Rejection is not that big of a deal. Trust me. It's not. It happens to me every day. And what did Caleb say? Well, he said, okay, will you go out with me? Cute. I said yes.

And I wrote my number on his receipt. Oh, wow. And then after he left, he had texted me a couple of times. Okay. But there hasn't been an official date yet. He said he was really timid. Did you bully him into a date? Like, I wouldn't say bully.

I would say strongly convinced. Yeah. I mean, he could have said no, too. I'm totally kidding. Right. You weren't shy and you love that line that she just gave. Yeah, I loved it. So maybe it's universal.

Yeah. Do you think he just doesn't know what to do on a day? Like, I'm being serious. Like, doesn't know where to go or like what to plan? I think because he is so shy, maybe all of this might be a little overwhelming for him. Maybe he doesn't actually, like, act women out on the regular. Or do you think maybe he's taken already and was also being a little bit sneaky with you? I'm seeing too.

I know how they move. Yeah, yeah, yeah. Like a cheater? Yeah. He's a mama's boy. Yeah. It might be possible he put the perfume on his mom and then he was like, oh, wow. What, Jeff?

Don't continue. You know what? Like, we already did a lot of jokes. That would do it too. I'm just saying it's a possibility for a shy boy. He's dating his mom now. Is that a possibility? Shy boys want to hook up with her mom?

Let's put everything on the table and then we'll find out the truth when we come back. Why don't you like this? We're going to call Caleb and find out who he really wants to go out with in your second-date update. Let's set some rules for Jeff. It's happening right after this. Brooke and Jeffrey in the morning. Second date update. You're in the middle of a second-date update update, and we're going to find out how the couple is doing right after you here, part two.

If you're a shy boy who's buying perfume for his mom this holiday season. What, Jeff? Be careful. Why? Because it might be a trap. Maybe you want to track, Jeff. You maybe do. And I say that because our listener, Denise, is a purposeful dater.

She tries to put herself in situations so she can meet available men who aren't on the apps. Yeah. Like in a previous episode, she was trying to meet guys at the golf course. But now, since it's around the holidays, she's been trying to meet single men at the perfume counter by working there part time. Yeah. Yeah. That is commitment. Perfume's not cheap, so it kind of checks for boxes.

Right. available, probably well to do. It's thoughtful, buys gifts. Bies gifts. Might be a little bit counterintuitive, but there are lots of clueless guys out there who need help shopping for presents, hopefully for their mother or for their sister. Or maybe

there's a guy out there that's buying perfume or cologne for himself. For the homeless. Yeah. For chair? The homeless. You know, you bought some, come on, bro. I think they need other things first. Yeah. Oh, man.

Don't go around spritzing the homeless. That's just not a good move. But it is how she met Caleb and she even kind of pushed him into asking her out. Problem is he hasn't followed through with the actual date yet. So that's where we're going to try and step in and help. Denise, Are you worried that we're going to scare him even further? Like, he's a shy guy.

I mean, it has been some weeks, so I definitely need the help. Okay. I can't do it. I'm going to come off to push him. I'll scare him away. Yeah. I mean, if it's been weeks, what does she have left to lose at that? this point. Yeah, what is going to ghost her even more?

She keeps doing the same thing. No one's going to happen. That's true. All right. Well, we'll try to talk softly and not frighten him. No one's talking softly in this room. Okay. Well, we'll be delicate with your shy future boyfriend and we will try and get him to say yes to actually going out on this date with you. So here we go.

Okay. We just need him to say that. Here we go. Hello? Hey, is this Caleb? Yeah, this is Caleb? Hey, man. Uh, this is, a radio show. Oh.

It's very strong, Jeff. Good morning. Yeah. Hi. Hey, good morning. Morning. He's friendly. We're a show.

We're called Brooke and Jeffrey in the morning. I don't know if you've heard of us before. I believe I heard of it. Okay. Okay. Well, maybe you've heard of this segment that we do. That's called the Second Date Update, where we try to reconnect listeners after they've met up once and they're having trouble seeing each other again.

Yeah, I think so. Okay. Okay. All right. So that's what we're trying to do here. here with you because one of our listeners, Denise, has been trying to get a hold of you. Denise? Yeah, remember Denise?

Denise smells good, Denise. You met her by perfume. Yeah, yeah, yeah, yeah. That's why she said that. Well, this must be a joke because I've been texting her. Yeah, we heard that. But Denise feels like you haven't made enough of a push to actually go out on the date. Yeah, I just, I just can't go out with her.

Oh, no. Never? Is there a reason? No, it's. I want to. It's just not the right time. Not yet. Not yet. Not yet. What do you have to wait for, brother? Yeah. What does it mean? I have some things I'm working on, working on myself. I mean, with all due respect, people are dating. They have busy lives. And sometimes they just can't wait forever. So we're just trying to figure out. Like how long this self time is going to take. Exactly. We're talking another week or are we talking two years? Well, I'm not exactly sure.

I ordered some special supplements and I'm trying them out see whether they're effective. What kind of supplements are we talking about if you don't mind me asking? I probably shouldn't say more than I did. Oh, we didn't need to get into a private matter. You're doing steroids, bro?

No. I was thinking maybe hair loss. Is that what's going on? Well, it does have to do with growing. Oh my God. Okay. Yeah, we really shouldn't ask anymore. I don't want to speculate anymore.

Stop asking, my bad. You're testing out supplements, it sounds like, and seeing what works. Are you asking, Jeff, because you're wondering what the results are for yourself? My motives are none of your business. Yeah, just like also, what are you taking? You really want to be ready for Denise if it goes well. Okay. Okay.

I mean, I think supplements are no supplements. You could do that. You could be there. Yeah. I'm just trying to hype him up. I feel bad for him, okay? I don't think it works. I'm trying to be one of the guys I love it.

I'm trying to like make it feel better. I don't want to feel bad about whatever it is. I know what Brooks trying to say. She's trying to say, Caleb, truly a lot of people think that they have it in their mind. Oh, I'll start dating once I lose five pounds or once my hair transplants come in. You're waiting for the perfect moment. But there really is never a truly perfect time. You just got to say, you know what?

I like this person. I'm going to go for it. Yeah, I guess that makes sense. I just think Denise is really going to like it. I don't notice it. But confidence is good. There is. And I don't know if this is a good thing or a bad thing, but I have a feeling you would never go out with Denise unless I told you that she's actually on the phone right now, listening to this whole thing.

Oh, hi, Caleb. So embarrassed. No, it's okay. I'm flattered that you, you know, you really want to. be ready for the date. Yeah. That's cute. Thank you.

Yeah, of course. I mean, you don't, you don't need to take supplements or whatever it is just because of it's bad. Yeah. I just, I think he'd like it. I want to respond to that. I hope I'd like it. I, oh, my goodness.

I have a new one coming in this week, and it's, Really promising. What do you mean a new one? How many of you tried? Yeah, like. It's called beard burst. I'm trying to get facial hair. What?

Oh, wait, what? It's a facial hair growing thing, he said. What did you just say? Beard burst. It's her facial hair because beards are really hot right now. Oh. Brooke just fell out of her chair. That's amazing.

It's about facial hair. Yeah. What? I want to grow my hair. Oh, my gosh. Oh, my God. We've been so delicate with him. What did you think it was?

What? I don't think I'm allowed to tell you. Oh, God. Did you think I was trying to order a B. Your drug? Oh, my God. Oh, God. But yes.

I don't have facial hair, and I wanted to get bigger, and I just can't grow it. Okay. Nobody cares about that. Listen, I am pro-w wanting to feel better about yourself, so you know what? If you're on this beer journey, I will go on this journey with you.

Wow. A beer journey together. That doesn't mean you're going to grow your own, right? I know. I sounded kind of desperate, Denise. How about this? As long as I can be your personal facial massageum, I think we can make this work. Wow.

This massages sound beautiful. I like that. The best offer we've ever had. Denise is tired of working at the perfume stuff. It's a much better offer than the one that I'm about to give, where we're going to pay for your next date. If you'll agree to see Denise one more time, Caleb. Oh, yeah, absolutely.

I really want to see her. I just hope you don't need a Hensworth at the perfume counter and kick my ass to the car. No, I'm sure Hemsworth would have nothing on you, sweetheart. Oh, wow. She's great, bro. You got to keep her. Have you looked at a photo of him recently? Yeah, I was going to say she's great at lying.

Yeah. I did meet him at the perfume counter guy. Okay. That's true. You did make commission off him. That's right. We started on a mission to get Denise a date from her perfume counter, and she found her perfect Hemsworth look-alike.

Well, soon they'll be looking like Hemsworth. Sounds like the opposite of Hemsworth. Caleb. You're the man, Caleb. Yeah. Thanks. And tonight I'm going to delete my Tinder profile. Oh, that's a big deal. All the ladies mourn.

Brooke and Jeffrey in the morning. Hey, I'm Ruby Carr, the host of the podcast, Oncore. out our brand new episodes featuring music from the show that everyone is reheating as we speak. Heated rivalry. Join me as I go behind the songs that brought Shane and Elia together. I'll tell you the stories of Fice, My Moon, My Man, Wolf Parades, I'll Believe in Anything, and tattoos all the things she said, and how they all became a part of this global phenomenon. Stream encore on IHeart Radio, Crave, or wherever you get your podcasts.

What's up, fam? I'm sports journalist Ari Chambers. Hey, what's up y'all? It's your girl, Sam J. And we're the host of everyone watches women's sports, a new podcast from Together and I Heart Women's Sports. Because let's be real. Women's sports is giving us way too much to talk about these days. So Kelsey Finler, she became the first female solo rower to go from California to Hawaii. My first thought is, like, what's up with the snacks? Like, what are we eating? The highlights, the rivalries, the breakout stars, the moments to take over your entire timeline. And the conversations that start during the game and somehow,

keep going all week. Every week, we're breaking down the biggest stories across women's sports. Naomi Osaka showing out. She beat Sabalinka. Shout out to you, Naomi. You get the palm, Naomi. You get the palm for that. Because we're not just interested in what happened.

We're interested in why everyone's talking about it. Because everyone watches women's sports. Listen to everyone watches women's sports. On the IHeart Radio app. Apple podcast or wherever you get your podcast. Last time we spoke to these two, Caleb was waiting for his beard burst supplements. to kick in.

Oh, God. And we got a lot of text at 785.92 from listeners who said, Caleb, the way you described it made it sound like it was something else. Did anybody else say anything to you about that, Caleb? Oh, yeah. Oh, yeah. I bet you got made fun of a lot in your friend group. Yeah, they all said, you know, I said it weird.

Yeah. And the one thing that I do want to make clear is the beard is the only thing that needed help growing. Oh. Okay. He needed to clarify for the lady. I've been waiting for months to hear that. That's good.

He's had months to think about the one thing he wanted to tell everyone. I'm glad we got that out there. But more importantly, though, how is your relationship with Denise? Because that's the whole reason why we have you on the show today. Is Denise there? Yes, I'm here. Okay, good. How are things going with you, too?

Things have been absolutely great. And actually, Caleb is getting a little bit famous because of this whole situation with the beard. What do you mean famous? Do people recognize it for the second date? Yeah, how? So I guess the company who makes the pills, they heard him on the radio. No. And they asked if he would endorse them and be an online influencer.

Are you kidding me? That's awesome. He probably came out of a link and get a percentage of sales or something. Don't let our sales department hear this. They're going to die. I know. It was that easy? They're going to approach me soon.

Jose, you want to grow a beard? Oh, my God. Caleb, that's amazing. How does that make you feel? Well, I never thought I'd be a beard grow influencer. Kind of niche, I guess, but now I don't have to pay for the pills anymore. So that's true. And you give me some money.

And think of Christmas time, you can put ornaments in it and stuff, dude. Yeah. You can really go for it. You're the manliest of all men now. Seriously. You guys should also. know that the beard really does look great.

Oh, good. Hide that undefined jaw line. Okay. Yes. I'm just really happy that you guys convinced me to give him another shot. Oh, that's so cute. Oh.

Hey. Well, look at that. We're glad that you two are doing well. You're still together and now you're more famous than any of us will ever be. So congratulations and keep us updated on what's going on. Make sure you follow us on our podcast if you're listening.

Like, subscribe, wherever you get yours at Brooke and Jeffrey. No, and now, Caleb, you can't shout out yours. Okay, you're already getting paid for it. This is our show, but get off. Hey, Portlandia fans. Carrie Brownstein and Fred Armisen here. The Dream of the 90s is alive in podcast form. We're launching Podlandia, A.O. rewatch, our brand new podcast where we revisit every episode

of Portlandia together, breaking down sketches, going deep on our iconic characters, and pulling back the curtain on how it all got made. And we'll also be joined by the PEOPLE. who helped bring it all to life. Guest stars, collaborators and friends, including director Jonathan Chryssel, the mayor himself, Kyle McLaughlin, legendary musician Amy Mann, and many more.

Kyle is going for it here. You fully improvised, not just words, but a song. Well, I thought you were all going to write a song. I remember you thinking that. Listen to Podlandia. A.O. Rewatch on the IHeart Radio app, Apple Podcast, or wherever you get your podcasts. What's up, fam?

I'm sports journalist, Ari Chambers. Hey, what's up, y'all? It's your girl, Sam J. And we're the host of Everyone Watches Women's Sports, a new podcast from Together in I Heart Women's Sports. We're breaking down the biggest headlines. Naomi Osaka, showing out. Shout out to you, Naomi. The viral moments.

I've been obsessed with Kashan Rock's boxing journey. She looks good. Her combos are swift. And the stories everyone's talking about across women's sports. Because everyone watches women's sports. Listen to everyone watches women's sports on the IHeart Radio app, Apple Podcast, or wherever you get your podcast. I'm Nick Tutro.

You probably know me for men. NYPD Blue, the longest yard, or Spike Lee's Black Klansman. And on my new podcast, Delivering Happiness with Nick Tatoro, I deliver pizza to a new guest. I've shared a slice with everyone from Seth Rollins. What are you doing, my belt? To Bill Burr. I don't think I've ever met somebody so exactly out of their mind as I am. And now, we even have more great guests coming up, including the great John Tuturo.

It's called Happiness, delivering happiness. And many, many more. Open your free High Heart Radio app. Search Delivering Happiness with Nick Tuttle. And listen now. This is Chelsea Handler from Dear Chelsea. Every week, the news gets worse. The world gets crazier.

And Yamanika is here to tell whoever's responsible, you're the problem. Do you know I just found out who Sidney Sweeney was? If he got a bunch of women, then I should have a bunch of men. Do better or do less so I don't have to do so much. I'm Yamanika, and I'm out. Listen to You're the Problem with Yamanika on the IHeart Radio app, Apple Podcast, or wherever you're. get your podcast.

On Raiders of the Lost podcast, we explore cinema like no one else, including huge interviews with stars like Ryan Gosling on Project Hail Mary. It was like the Jaws Shark. Didn't always work, came with its own problems. That's what made it great. The cast of Obsession. On set, there was so much magic happening with each scene we were putting together. Deep dives into classics like 2001 of Space Odyssey or Fight Club, plus weekly episodes

on all industry news. Listen to Raiders of the Lost podcast on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. And for more, follow at Raiders of the Lost podcast and at TikTok Podcast Network on TikTok.