Brooke and Jeffrey: Second Date Update - Second Date Update: Surprise Surprise

Episode Date: August 10, 2026

One of our listeners got one of the BEST compliments a guy could get from a girl at the end of the night, but he’s PUZZLED why she’s not calling him back! We’re on the case in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

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 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. 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. 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 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 Tatourl, 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 Totoro. And listen now. Summer Blockbusters are back. The Odyssey and Spider-Man. Brand New Day have taken over cinemas. And Raiders of the Lost podcast has. all the coverage you need, including our interview with director Destin Daniel Cretton. What surprised you about Tom Holland? He shows up to every meeting early. He's the first one on set.

Aside from learning all of his lines, is also able to memorize everybody's name on set. Download the free IHeart Radio app. Search Raiders of The Lost Podcast and listen now. We're going to get you started on Monday with a brand new episode. Thanks for finding the official second-night podcast with Jeffery in the morning. I've been seeing another info. flux, by the way, of like Facebook videos. That's random. I know, of people stealing our audio and then using weird AI pictures of Jeff and I. Brooke, are you on Facebook seeing these are people are sending them to you?

No, it's just in my algorithm. Oh, huh. I like that. I do appreciate that it finds me. Yeah. So that's nice. Target audience has been reached you. Yeah.

So if you've come here from social media, thank you for finding the real stuff. We appreciate it. Yes. But first, let's get to comments. Yeah. Well, that makes me think of this comment by. M. Pickle who said, dang, they still make these? Yes.

And Piggle. We do. We do. Well, some people get stuck on those playlist. Yes. And they don't realize that there's a whole show that you could click over to that has, like, years of new episodes. Please go comment on that stuff for us.

We can't because then we look weird, right? So maybe you can do it for us. Yeah. And it's just hard to keep up with it. Honestly. All right. Hey, thanks for being here in the present. Yes.

New episode just for you. Brooke and Jeffrey in the morning. Second date update. Brooke, how would you feel if you came home and your husband tells you he has planned a date night? Oh, I'd be so excited. Child care is handled, and what you're doing is a special surprise. Oh, I love surprises. This sounds cute.

Surprises are like my jam. Don't tell me. Don't tell me because I would want to be surprised. Wow. Baby number three would happen that night. It sounds like. Oh, yeah. And you could surprise him.

No, he got snipped. We're good. Now, imagine there's no kids, no husband. Uh-huh. And it's a first date with a cute guy you just met online and did no background check on. Oh. And he says he has a surprise for you. Yeah.

Are you still feeling the same way? Uh, no. No, no, I'm not. Weird. Why didn't I do a background check, Jeff? Not even sketched me out. You're just an accepting type of lady. Oh, okay.

I only ask, because that's the approach one of our listeners, Wesley took on his first. date. He thought it'd be fun to be a little bit secretive about what they were doing. But now he's not getting a call back. So we'll see if we can pinpoint any clues for why that might be happening. Because I feel like we already found the big reason.

It could be. But Wesley, welcome to the show. Hey, hey, guys. How's he going? That's a big, bold move planning a surprise date for a very first meetup. So what's her name? Let's start there. Ramona is her name. Okay. Can I ask, did you have any inclination that Ramona likes surprises?

Because some people absolutely hate him. Good point. Well, I mentioned the idea of like, oh, it could be a surprise if you want. She was like, yeah, let's go for it. Okay. That's a good way to bring it up. It was like you put it on her if you want, right? You choose.

I like that. Yeah. So what did you end up doing for your surprise date? Well, it might be a little bit cheesy, but when I picked her up, I left a trail of rose paddles from her door. to my car. That's very romantic. Oh. Wow. That's what I'm saying.

I would immediately think that means you want to do it. Brooks, it's unbuckling her belt. All right. Well, I get the hand. I'm not going to say no. The rose petals usually go to a bag. So it's like. It's strange or back seat? Okay, but no, on a first date, it's kind of like a path to romance. He has a station wagon. Thank God. A lot more space.

All right. What did Ramona think when she saw the rose pedal? She laughed, but she said it was really sweet and kissed me on the cheek. Wow, you got kissed on the cheek immediately? Yeah. Yeah. Wow. Okay, so you're starting off on the right foot. That sounds pretty.

What happens next? So for like the surprise part of the night, I took her to this couple's Mediterranean cooking class. Oh, my gosh. That's actually really cute. I would love that. And you had her cook the meal while you just sat there and waited, right? No, he did a trail of all of it. So she had to follow into the...

There's some feta crumbles out. Yeah. Okay, no. All right, no, that's cute. What did you guys cook? Um, I had never heard of this until we made it. It's a hummus and seafood paella. You guys know what a paella is?

Yeah, paya's amazing. Hummus and seafood pious sounds awful. Oh, it was so good. I think you mean those are separate dishes. Yeah. That is so nice. Oh, yeah, yeah, yeah, yeah. It was her and I,

shipping on wine. And it was just good conversation. You know, we were flirting, we were talking about ourselves, that whole thing. So from how you're describing it, at this point, things are going pretty perfectly. There hasn't been any speed bumps yet. Exactly. Yeah. So nothing has gone wrong, but she just kind of stopped responding to me, kind of ghosted me a little bit.

Hold on. We don't know how the date ended. Yeah. Like how did you and Ramona leave it? Okay. Okay. Well, that's a good question because I don't think anything messed up there either. Really?

So, yeah, we get in the car. She kisses me again. And then I drive her back to her house and she says, I don't want this night to end. Oh. Oh, my God. That's what she said. That's the best thing of broke and say. Why is that good?

What do you mean? Why is that good? I'm asking why. It's confusing to me because this whole situation, but we ended up making out in the car for like 30 minutes straight. I knew the rose pedals were leading to car action. I knew it. I called it all along. And then what?

You walked her to her door or? I walked her to her door and that was that. It was kind of a late night at that point. And you didn't push. I mean, I bet you were so. Yeah, you should have pushed for more. Right. I mean, yeah.

Get out the rose pedals again. Yeah. I bet you were so giddy. Like, what were you feeling when you got back in your car? I felt great. I felt like I had done everything right. And I was feeling really optimistic. I was really excited.

This is a girl that I really like, so I don't understand why we're suddenly not about why she all of a sudden stopped answering me. Yeah, not even a word. Like completely. She didn't say I don't want to. Did she say anything after the date? Well, after the date, yes. We texted for days after that. Oh. There has been communication. We were just texting, but it wasn't just the normal like, hey, how you doing? It was kind of lovey-dovey stuff. kind of, you know, there's a second date on the horizon type of stuff. Okay. And then when was the last time you talked to her?

A couple days ago. Well, maybe it's like I said before, she didn't want the date to end because that means she goes back to her boyfriend inside of the house. It's like that was her one night of freedom. It's going to be awkward since he didn't pick up those rose petals when he comes out. Yeah. So is it possible? I mean, do you think maybe there could be another dude? You've only been on one date with her?

Well, I sure hope not. We seem to have a really good connection between the two of us. That would be kind of messed up if she was going home to somebody else. And it's something that you'd want to find out right now. Yeah, sadly, I hope that's the answer for you, brother. Because there's nothing to do with you. No, that we can't fix that. She's an awful person and it says nothing to do with you.

We're trying to fix this and get him another date. It could be just a bad communication. Sure, but if it falls apart, let's hope it's her on her. Maybe it's a little bit of both. Let's hope for that. When we come back, we'll call this girl and find her. out why she isn't wanting to see you again after the most romantic date that I think we've heard all year long when we do your second meet update right after you don't think so now you're doubting yourself it was kind of a bold statement I don't know I'm trying to remember the other day after the most mid romance date we've ever heard in your second date update right after this broken Jeffrey in the morning second date update dude talk about a cool surprise date that didn't involve ropes or duct tape yeah That's hard to pull off.

Shockingly. Wait. Why are you acting like that's a normal thing to say? This is what all women expect. The first time a stranger picks them up at their house and says, I have a surprise for you. Okay. Our listener, Wesley, went a different route, connected with a woman named Ramona online, picked her up at her house with a trail of rose petals leading from her door to his car.

And she loved it. Yes. Well, at least that was the vibe she gave. Definitely. And so they ended up doing a Mediterranean cooking date. where they learned how to make hummus and paella. How awesome is that? Separately, we discussed this separately.

And when she got home, she said those magic words, I don't want this night to end yet. Oh, I don't think any girls ever told me that. That sounds magical. I want a feeling. That led to a half-hour-long makeout in the car, followed by a string of romantic texts afterwards until things suddenly stopped,

and he doesn't understand why. So you can imagine if you're in Wesley's shoes, you want to know what is going on. God, I really hope it's, I broke my phone and it's taking me a couple days to replace it. I got the replacement. Wouldn't that just be the best thing ever, Wesley? Yeah, yeah, ideal situation there. Yeah, for sure. She's like, I never want this phone call to end now.

Yeah. Then we got a lot of talking to do. Well, we'll see if her phone is still working because I'm about to dial it right now. I'm nervous for you because there's a lot on the line. You invested in this date. You know when you like this girl. Usually these things don't matter when we call people. Yeah.

Or as much anyway. Yeah. Not to downplay all of our other listeners. But sure. This one definitely has a lot of weight behind it. We're invested. Let's dial Ramona's phone number and see if she answers. Here we go.

Hey, is this Ramona? This is she who's calling? Hey, Ramona. My name is Jeff from a radio show called Brooke and Jeffrey in the morning. Hey, Ramona, the whole show's here. Hey, Ramona, good morning. Okay. Good morning.

You don't have to be afraid of us. We're pretty friendly. We're friendly. We're funny. What are we doing? We're doing a segment here. It's called the second date update. Oh. Okay.

That maybe means that she's heard of them before, Jeff. That type of reaction. Maybe. This is a segment where if you go out on a date with somebody and they're not getting a call back afterwards, you can reach out to us and we'll try to get a hold of that person to find out if there's reason why. Oh, and we have one very confused man. Oh, yes. Yes. No, no you don't.

You don't have a confused man. I don't go on very many eight, so I know exactly who you're talking about. Oh. Oh. It has to be Wesley, right? Yeah. It is Wesley. Wait, he's very confused, though. You know, he's not just confused. He's in a-hole.

Okay? Whoa, whoa. I'm never talking to him again. Not our Wesley. That's not the guy we talk to. Dude, that's wild because that is not who he portrayed towards us. Like, he sounded like a hero of a first date. And romantic.

Night and shining armor. Well, I've already blocked him, so we really don't need to have a big conversation. First of all, we didn't know that. I don't think Wesley knows. He never mentioned that he was blocked. Then he is both rude and stupid. Okay. I'm sorry. I'm sorry,

Ramona. We need the details of this. Because the story he told was the most romantic first date and rose petals. cooking classes. Well, first of all, it has nothing to do with the date. It was a lovely evening. Oh. Oh.

I've never heard the words, lovely evening uttered with such disdain. Is it something you found out after? Is that what you're saying? Yeah. He body shamed me over a text. What? Whoa. What do you mean he body shamed you?

Oh, body shamed? What did he say? I'll get mad for you. Oh, no. What do you mean? He thinks that I have this giant, big, Fred Flintstone forehead. I mean, seriously, how

how dare he, and he texted me that. Hold on. He texted me that. Hold on, hold on, hold on. You felt like Ramona, he was pointing out a flaw with you. I don't feel that way. I read it. He sent it to me. I can read it over and over.

Oh, can you read it to us? What exactly did it say? I'm not going to read it to you because it's going to make me feel bad all over again. Oh, okay. Well, that is absolutely not what we're going. after you. Dude, no wonder you blocked him if you felt like he was making fun of you. I'm not going to sit back after one day and let some guy pick on me.

I mean, my God, I got better things to do. We got a very different view of what was going on between the two of you from Wesley. So I'm really interested to hear his side of this and figure out what's really going on. Because I need to let you know, Ramona. Wesley is already on this phone call listening and waiting to talk to you. Oh, well, that's just great. Wesley, are you even there? Romota.

Oh my God, I never body shamed you. Oh. You can't say that. I wouldn't. I wouldn't come in with that one. Wesley, please, tell us that there has been some sort of horrible miscommunication here. And you're not doing the things that she's accusing you of doing. Well, I'm not here to make her feel bad.

But in my defense, I'll tell you what I said is, I wish you were here. so I could give you big forehead kisses. Did you say big forehead kisses? Yeah, I did. I said I wish you were here so I could give you big forehead kisses. Oh my God. Okay.

That means big kisses on your forehead. It doesn't mean you have a big forehead. Yeah, I don't know if it really sounds like body shaming. No. Oh, Ramona. I'm so sorry you read it that way. I bet you felt so bad. I got he was being playful.

You guys aren't understanding. ending. I got his text. I specifically read it. It said big forehead. You can't just unsee that stuff. It's just an unfortunate way of wording it. I mean, I could see Ramona if you had some like self-conscious things that you would read it that way. But I think everyone in the room is trying to tell you that was definitely not the intention. It was cute. It's not cute. I mean, we're trying to defend him. But Wesley, talk to Ramona. Tell her what you meant. What I meant to say was that I want to lay a big kiss on your forehead. On your normal forehead.

Yeah, I'm not saying I want to kiss you on your big head. That is a funny thing. Right. Are you hearing him? It's going to take a long time to cover that dome. But you said big forehead. Those are your words. You texted it in that order.

Oh, my God. Technically, she's right. I know what I said. But people always say give you a big forehead. It's just a term. You need to tell me right now, honestly. I'll know if you're lying. I mean, when you texted me, did it or did it not come into your mind subconsciously

that I have a big forehead? No. No, it did not. See? Okay. So now you don't think I have one, but every time you look at me, you're not going to think about my forehead being a little bit too big. After this conversation, maybe.

I mean, Maybe you could say it slightly bigger than normal, but not that much. But I don't mind. I don't care. Okay. Well, he likes it. In a big forehead, is it a bad thing? Yeah, it's not.

That's a lot of head to kiss. You get extra forehead kisses. You are not helping. Sorry, I'm trying. Yeah, you guys don't know how to make a girl feel good, do you? Oh, we're kidding. You got to lighten up a little. Ramona, you have a romantic guy who's seriously interested in you, who put in a lot of effort

and he really wants to see you again. Like, that doesn't happen very often. Yeah, we don't hear about this a lot. We really think you should give him another chance. I mean, if you want to on your next meetup, you could wear a hat so the forehead is out of the picture. Or just pick a body part of his to shame. You know, then you got your equal. You're roasting together, T.

I don't know about that, but Ramona, we think you should give him one more chance. Forget that one text message because everything before it was so good. Meet him one more time. and if you're willing to, we would pay for the date. I think that you guys have had enough of a laugh on my part. And I'm just going to say no. I don't need it. What if you at least unblock him?

No, no. Just let it go. Let it go. Let it go. It's done for nothing. Ramona, I'm really sorry it worked out this way. And for the record, I think your forehead is normal. Like maybe it could be slightly bigger, but it's not,

No. It's normal. What are you doing? I just want to give her closure. She's going to be thinking about this. She's got a lot of head to think. Yeah, she does. Let's leave her life.

Brooke and Jeffrey in the morning. IHart Radio invites you front row for IHart Live at the Horseshoe. With Brent Smith and Zach Myers of Shinedown. Here acoustic performances of fan favorites, second chance, a symptom of being human and the brand new single Young Again. Plus, Shannon Burns sits down with the guys for an exclusive conversation about the music,

the stories behind the songs, and what's next for Shindown. Search IHeart Radio, CA on YouTube and stream the full experience today. 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 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. That call was such a weird ride. Because when we first heard her say that she got body shamed, I don't think, I don't think anybody thought she was talking about her forehead. No, and you know what, though?

Everybody's self-conscious about different things. and I get that, but, like, it's interesting to, like, even still not be able to hear what he was actually saying. Yeah. We definitely didn't help. No. No, we did not. I just think we're all caught on our heels with that one. And I'm not even shaming the size of our heels when I say that.

But it is a shame because it just felt like no matter what we said, how we tried to frame it, she was not going to budge. No. Some people just can't laugh at themselves. Yeah. And I won't use the term hardheaded because I know how that's going to go. Yeah, don't do that. But she was not going to change her mind. Yeah.

She's like, excuse me, I was born with a soft spot on my head. Yes. You know, it's too bad that didn't work out because I really felt like there was something there. I know. She's like a prisoner in her own head. Yeah, we need to stop saying head, I think. Oh, sorry. You know what?

We can help you in your personal life if you ever need help getting a second date. Reach out to the show. We'll call that person who's not calling you back. Yes. 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. It's a new podcast from Together in IHeart Women's Sports. We're breaking down the biggest headlines. Naomi Osaka, show it 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. Hey, Portlandia fans. Carrie Brownstein and Fred Armisen here.

The Dream of the 90s is alive in podcast form. 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 about it. I thought you were all going to write a song.

I remember you thinking that. Listen to Podlandia. A.A.O. Rewatch on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. 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 a bunch of men. to do so much. I'm Yamanika, and I'm out. Listen to You're the Problem with Yamanika on the I Heart 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 Totoro, 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. 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 Titoro. And listen now. Summer Blockbusters are back. The Odyssey and Spider-Man. Brand new day have taken over cinemas, and Raiders of the Lost podcast has all the coverage you need, including our interview with director Destin Daniel Cretton. What's surprised you about Tom,

Holland. He shows up to every meeting early. He's the first one on set. Aside from learning all of his lines, is also able to memorize everybody's name on set. Download the free IHeart Radio app, search Raiders of The Lost Podcast, and listen now.