Brooke and Jeffrey: Second Date Update - Second Date Update: Special Friend Fun

Episode Date: July 24, 2026

Dating has become so complicated & expensive… where if you DON’T FEEL IT in the first 30 seconds… there’s NOW a sentence you can say…. that gives you an instant FREE PASS to get out of it… It happened to one of our listeners in today’s Second Date Update!See omnystudio.com/listener for privacy information.

There's no shortcut for saving time, but saving money is simple. Just combine your car and home insurance with Bel Air Direct and save. Get a quote at bellair direct.com. 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 season. scene we were putting together. Deep dives into classics like 2001 a 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. 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 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, AEO 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 I Heart Women's Sports. We're breaking down the biggest headlines. Naomi Osaka, showing out. Shoutouts to you, Naomi.

The viral moments. I've been obsessed with Kashan Rock's boxing journey. She looks good. her combos or 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 Podcasts or wherever you get your podcast. This is Chelsea Hamler 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 Podcasts, or wherever you get your podcast. All right, welcome to the official podcast. Thank you so much for being here. Before we get into today's brand new second date podcast, what do we got on comments?

Yeah, well, on yesterday, Brooke breaks you up. Big Till commented and said, since you guys do Brooke breaks you up, you should start a segment called Alexis Arranges a Date. We're callers calling to have Alexis get them set up on a date with somebody they like. I've done that. Let's lean into more of the alliteration and go Alexis arranges annulments. Oh. And just find any newlyweds that don't want to be wed anymore.

Aren't they talking about Alexis as you out? Oh, that's not as fun. No. They're talking something out. But you're right. That is, yeah. All right. We'll work on it.

We'll work on it. Right now, enjoy this episode. It's Brooke and Jeffrey in the morning. Second Date Update. Here's a little secret. When we get emails for this segment, sometimes people like to share their dating journey. Oh, there's no secret there, Jeff.

It's like in the title, that's what. No, I mean, more than just like the date that we're talking about. Like, I matched with 52 people and I found 51 had dated my stepdad. I see. But that means this one is good to go. Man, that stepdad. Must be a pro athlete. Well, we need the context to know why they're here.

Exactly. It's helpful in that way. And I was just using that as an example because this segment can obviously get weird. And today, our listener, Melanie, mentioned in her email that she had a bump in the road on her dating journey recently. And she'd be willing to share that with us. So, Melanie, I know that the guy that you're emailing about, his name is Scott, but apparently there was a date scheduled before that. Can you tell us that story? Yeah, so not my best moment.

Uh-oh. Yeah. That's right. We've always had, everyone's had those moments. So what happened? So we're meeting at a bar, basically. And then he texts me that he's going to be 15 minutes late. And I'm like, oh, that's not a big deal.

Whatever. At least he's texting me. Yeah, gave you a headset. More time to take shots beforehand. Go ahead. Oh, I used to do that, though. I didn't get loose. And I'm sure that that works out really well.

I fit in three. You're 15 minutes late. This is your fault. Okay. So what happens? So he comes up to me. He shakes my hand like really awkwardly. And then he says, I forgot my idea home.

So sorry, I'm going to go back and get it. And then he never comes back. Oh. Girl, that's not anything to do with you. Yeah. What do you mean? Not your best moment. Yeah.

That's his bad. Why are you embarrassed about it? Well, because obviously he saw me and then didn't want to do the date. Oh, you think it was an excuse. I hate him, Melanie. You don't listen to him, okay? You're hot, you're beautiful, you deserve someone better than that. Okay, laying on a little bit thick.

Well, we don't really know. That's messed up, man. It is messed up, though. No, we're not defending him. We're saying good riddance to that last guy. Let's move on to this new guy, Scott. Oh, I thought this is the guy we were calling. No, he was the last loser.

He blew his shot. Tell us about this new man. Well, I took a break from Tinder for like a month because that was just... Yeah, shook you. I get it. Right, exactly. And so I thought, okay, I'll try again. And that's when I met Scott.

Okay. And he asked if we could just go for a walk on our date, which I loved that idea. Yeah, you don't need an ID to go on a walk. I mean, it sounds kind of cheap to me. That's a free day, you know? You guys. I mean, you're probably nervous even for you. for a walk at this point because of what had just happened to you.

Yeah. But it was nice. And he was really cute. He gave me a flower, just one. But, you know, we walked a lot all around the city, just talked about all kinds of stuff, hobbies, and both of us like to travel. So we talked a lot about that. Nice. And then it turns out I know one of his roommates, actually.

Oh, really? That's wild Small world Oh Yeah His name is Max And this is from like a few years ago I haven't talked to him in a while

We've kind of lost touch But wait You were just friends with Max Or was there more of a situation With Max in the past Um Let's say We're special friends

Yeah Oh boy That doesn't bother you At all No I think, though, it might have bothered Scott, and maybe that's why he's not calling me, because I think I was asking too many questions about Mac. Oh, yeah.

Either that or he went back and said, oh, my God, Max. And Max is like, you can't do this. Yeah, and told some stories about you or something. I don't think so. Okay. I mean, like, would you consider it an X, though, or just some, you know what I mean? Just a hookup. Yeah.

It's just special friends. Okay. For a long time? Yeah. Okay, you guys, let's get over Max. That's the whole point. We're saying about Scott. Right.

There must have been more good moments from the walk with Scott. Yeah. Yeah. At the end, I thought, okay, I'm going to make sure he knows I'm into him. And so I said, hey, do you want to go back to your place and have some fun? Whoa. After a walk in the middle of the day? Oh my gosh.

I liked it. I like her. Broad daylight holding a single flower. Of course, Jose likes it. Yeah. That is a big jump. Yeah. I just wanted to, you know, hang out and get to know him more.

Have fun, bro. Is that what you meant by have fun? What do you mean by it? Brooke, why don't you explain what you mean by go back to someone's place? I have a feeling that I would have taken that very wrong. Yeah. Yeah. Okay.

Yeah. She bust out scrabble? Brooke, like, wait a minute. Yeah, I have my pants off already. Sorry. Melanie, Brooke has a very, very dirty mind on this show. Everyone else not the same. It was mostly you.

That is not true. Yeah, Brooke, come on. They just want to have fun. The rest of us are very wholesome family oriented around here, Melanie. So what does Scott say to your open invitation? He said he had a few things going on and he wasn't sure and he would text me later, call me later. So after you left it with Scott, what's happened since?

Nothing. I never heard from him. It's been a couple of days now, and I texted, are you okay? And nothing. I think we're going to get either a story from Max or... Yeah, it's an old story or something. Some sort of definition of fun. Well, either way, you deserve to get the answers that you came here seeking.

So let's reach out to Scott. We'll see if he picks up. And hopefully he can explain. why he turned down your very enticing invite to hang out and play board games at his place. Yes, of course. When we do your second date update right after this. Hold on. Thank you. Brooke and Jeffrey in the morning.

Second date update. If you're just joining us, our listener, Melanie, was on a date with a guy taking a long walk through the city when she found out she knows his roommate. She described it as a, quote, special friend fun situation. Which, I don't know what that means now. I thought I did, but I'm not so sure anymore. Yeah, it's also true. Still, obviously, it complicates things. The main issue being she spent a lot of time asking about the roommate

and much less time actually talking about Scott, her date, himself. She tried to make up for it. Yeah. She did. That's why I'm... She realized it. She had kind of an invitation back to her place and back to his place. Any place.

Anyplace would have worked. But just to hang out. Yeah. Again, don't know exactly what the situation is, but clearly he has not spoken to her since. So my theory, Melanie, is it possible? Scott went back to his roommate, told him the story, and the room he said, whoa, be careful. She's wifey material. What?

And that thought scared him. What do you think? Perfect. What everyone was thinking, Jeff? I don't think that. That's it. Okay. But I don't know.

Well, I mean, it's still on the table. You wouldn't describe yourself as wifie material? You should think that's it. I mean, I guess, yeah. Yeah. See, anything's a possibility. Let's call Scott. We'll see if he even picks up and hopefully can clear this whole situation up for us.

Are you ready, Melanie? Yeah. All right. I'm excited. I'm excited. Oh, wow. Maybe we should tone that back a little bit. No.

I'm a little concerned about that. Maybe take a deep breath. That's good advice. I'm going to take a deep breath right now before we make this call. Nice. It is good. It resets. This is wasting our time, Jeff.

It was Brick's advice. Okay, I'm just going to dial the number. Here we go. Hello. Hey, is this Scott? Yeah, who's calling, please? Hey, Scott, you're on a radio show called Brooke and Jeffrey in the morning and the entire world is listening.

How are you doing? dramatic really overshot that one I mean is a prank the entire real thing is yeah we do we do pranks we do that but that's not what this segment is we're calling because you made one of our listeners

sad by ghosting her after your date who okay who that's a good question it's a woman named Melanie a lovely woman you went on a walk with no no no I'm Are you guys serious?

Yeah. Is this for real? This is a segment we do called Second Date update, trying to give you a chance to... No, no, no, no, no, no. I'm going to stop you. This has got to be a joke. I'm not doing this. This is crazy.

Okay, wait, hold on. Hold on. Whoa. That crazy is kind of a wild reaction. You guys went on a walk together. Yeah. I don't, I don't, I don't, I don't, did she call? Like, what is, I don't think, I don't like any of this.

Why are you so upset about Melanie? I know, I know this is an overwhelming experience for you. Scott, we're calling you out of the blue and I get that. But we're just trying to give you a chance to explain why after the date Melanie hasn't heard from you because she's confused. I don't think I should be talking to you about this, honestly. I don't know what to say. Why?

Yeah, really. Okay, she did tell us that she knows your roommate from the past. Are you kidding me? No, like I, yes, she knows my roommate. Like, I don't know. She called you guys. This is crazy. You understand?

Why are you having this reaction, Scott? Help us understand. I don't, I don't even want to say much. Like, I don't, I don't want to talk about this. I don't want to know anything about. I don't want to be involved in this at all. Okay. So did you tell your roommate that you went out with her?

Yeah, I told my roommate I went out with her. Okay. Okay, that's where we need to go next. What did the roommate say? What was the reaction? He freaked the fuck out. Why? I tell him, I tell him.

I tell him I go on this date with this girl named Melanie and he looks at me like I have four heads. Oh. And he's just like, let me see. I show him her picture. And he just, without saying anything or doing anything else, he just takes his phone out of his pocket and he dials 911. What?

Whoa. And he's like, dude, did she follow you home? Did she just, did she know where you live? Oh, my God. Is she stalking your roommate? I don't know. I don't know anything. the cops, they show up. No, they

actually came? Yes, they came. And there's like footprints in our backyard and he's like thinking it's her and like, I'm asking him about it and he's like, didn't want to talk about it. I don't know anything. I don't want to know. So Scott, your roommate didn't say anything about this. Like, did he provide any background?

No, he was just like, dude, leave it. Don't get involved. This is bad enough. Oh, my gosh. Okay. Okay. If the cops show up, That's all the background we need, Jeff. Okay, cops don't just show up when you see a picture of someone on a dating app. Yeah. The history of something.

I've had cops show up randomly and tear their pants off, but that was for a different sort of. Well, they sort of dressed like them. No. Okay. This is so bad. So, I mean, at this point, what do we do? Well, we have to tell him. I'm with you, but I don't know the right way to do it.

Why, you're not freaking out about this. We should not have her on the bottle right now, Jeff. and keep the situation tame. Do we hang up? Because, Scott, here's what you need to know. And don't freak out about it. Brooke? Or do freak out.

Please don't. But Melanie is actually on this phone call right now listening to it. No, no. It's okay. Oh, my God. I am so sorry. We are so sorry, Scott. I'm going to go.

No. I got to, I can't talk to her. You don't have to talk to her. Just hear her out for one second. And then if not, we can always have you leave. Melanie? I've got. Oh, God.

I miss you. Okay. Oh, geez, Melanie. Why are you so happy? What do you mean, where am I? I'm home. Girl, why are you being so calm? I know.

They just called the cops on you. And the cops showed up. What is going on? Listen, you know how Max is. He can be a little bit of a drama king. He can overre-you-live-with-in, you know. No, no, Max is super. chill. He's the chillest guy I know. The fact that he thought I followed you home, that's really

funny. Funny. Why? Why would that be funny, Melanie? Were you in their backyard? Look, that was just a special friend misunderstanding. And if Max doesn't want to be in touch anymore, I'll just have to be okay with it. Anymore? Stop calling him a special friend. You kept saying that. I our date and it's weird. You're weird. Well, did you talk to him about me? Does he forgive me? Because I forgive him. Forgive for what?

What would require forgiveness? Look, just because him and I are no-go, it doesn't mean that you and I, Scott, don't have a path to the future. You really have a talent for skirting around what's actually happening. Did you just, did you

find Scott because of his roommate online? God, I can explain it all to you later. I'm not going to do it here on the radio. Don't. Don't. Melanie, it will make you laugh. I promise.

It's all very silly. Melanie, we would like you to never contact us again. That's the bottom line. Don't ever call the radio. The news don't contact us again. Okay. I feel like now someone's being a little bit controlling in the relationship. Jeff, this is not a time to be.

sarcastic. Sometimes when you want something done, it's helpful to do a compliment sandwich. So why don't you say one nice thing about Melanie and then tell her never to stalk you again. Go ahead. She would really like that. Melanie, you know, like I appreciated the compliment about my shiny hair, but like it's kind of creepy. She's probably making hair dolls with whatever she collected. It's shinier than yesterday. Melanie, you got to leave these men alone.

They do not want to talk to you. They're sending you a very clear signal right now. Scott, if you change your mind, you know, where to find me, and we can have a lot of fun together. Now I'm scared, but her fun is, too. I will remember that. All right, I'm not even going to offer for another date.

I feel like we got the information that we needed. Hopefully, Scott, you got a little bit of closure out of this experience. And if you need more evidence, you can find the podcast up at Brow. Brooklyn Jeffrey. Good plug, Jeff. Good plug. Yeah.

Yeah, thanks. That's usually the message when we hang up. Melody, don't call us for another date. Brooklyn Jeffrey in the morning. There's no shortcut for saving time, but saving money is simple.

Just combine your car and home insurance with Bel Air Direct and save. Get a quote at bellairdirect.com. 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 that 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. Wow. If we had known

what she was really trying to do there, then we never would have made that call in the first place. Yeah, I think that is an important thing to be said. Yes. Yeah. We were misled. Definitely.

But it just occurred to me at the end of her first date when she said, why don't we go back to your place and have some fun? Now I know what fun means to her. Oh. I get it. It's still not fun to me. That's so weird. But to her, I want to confront your roommate for the restraining order he just filed against

me. That's fun for her. Never would have to guess that. No. No. That was not on my list. Why are the ones that sound so normal? Just end up not.

Turn out to be the most fun? Yeah. Someone's like, hey, I'm stalking you, but you got nothing to worry about. You're reading the word fun for me. She did pull the old Trojan horse move, though. She's not going to break into the apartment. She's going to get invited in by the roommate with the promise of good times. What a coincidence.

You guys are roommates? Weird. I love how she was like, well, how would I have. known that he was his roommate. I know the research idea. Did I just lock the door behind us as we stepped in here? How did that happen? Anyway.

Okay, let's be safe, everybody. I will say we blocked her phone and we blocked her email afterwards, so we should not be hearing from her again. Okay, good. Okay. And I hope those guys move soon. Yes. But we do need to hear from you if you need help with your dating life email the show. We'll call that person who's not calling you back.

It's going to be so fun. Can we just say if police are. involved, please don't contact us. Good disclaimer. 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 episode 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. 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 sketch, 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. Guestrars, 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 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. Sports on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. 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 get your podcast. I'm Nick Tatoro.

You probably know me from NYPD Blue, The Longest Yard, or Spike Lease Black Klansman. And on my new podcast, delivering happiness with Nick Titoro, 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 Tituro. 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.