Brooke and Jeffrey: Second Date Update - Second Date Update: Nanny No No

Episode Date: July 27, 2026

Katrina spent the last 20 minutes of her date with Raymond LOCKED in her car by herself. Why would she do that? There’s a reason and you can hear it in the Second Date 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.

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And many, many more. Open your free High Heart Radio app. Search Delivering Happiness with Nick Totoro. 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 get your podcast. On Raiders of the Lost podcast, we explore cinema like no one else,

including huge interviews with stars like Ryan Goss. 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 Iheart radio app, Apple Podcasts, or wherever you get your podcasts. And for more, follow at Raiders of the Lost. Lost Podcast and at TikTok Podcast Network on TikTok. Welcome to your new week and your brand new episode. Hope you're having a great Monday. It's Brook and Jeffrey in the morning.

We've got a brand new, a very official second date update for you in just a second. But first comments. Yeah. To Zvi, you know, it's just TZVI. That was good. Ziv. Said, this is crazy. I found you guys a little over a week ago.

And I'm listening backwards and I'm already up to May. I'm doing at least five hours a day. Oh, my God. Thanks, y'all, for being my summer. Dang. They commit. Yeah. You're calling us your summer, but technically you're going to get back to Christmas soon if the rate you're going.

That's a good point. That's a good point. So I'd like to say happy Thanksgiving to you. Yeah. There it is. There it is. All right. Your brand new episode starts right now.

Brooke and Jeffrey in the morning. Second date update. It's Brooke and Jeffrey in the morning. And I know some states have banned cell phones from classrooms. Yeah. But has anyone thought about proposing a bill that would block them? from being used on first dates. Ooh.

Oh, man. Very easy to, of course, control that. Yeah. More government interference in our personal life. Yeah, especially their dating life. Yes. They're not involved in that. That's where Brooke and Jeffrey stands.

I only bring it up because our listener, Katrina, blames her phone for ruining the momentum of her latest hangout. Yeah. And now she's being forced to use it again to call us for help. I thought now she was proposing legislation. Maybe that's the next step. Katrina, I am so sorry that our producer is making you use your phone to do this. Thank you.

I wish I could just throw it away. Oh, wow. I feel like that sometimes. I get you on that. I'm a dig into mine. I would throw mine away and then jump out of the window after it. Same breath. Well, maybe that came up during the date and caused some of the problems.

Why don't you tell us about this guy that you met? What's his name? His name is Raymond. And I matched with him on, you know, on the app. Okay. On the phone all over again. Here we go. We met on the phone.

And the phone ended up being our demise. Oh, no. What stood out about him on the apps? He's really cute. He's really cute. Just trying to come up with a deeper answer. That's fine. He's hot.

That's what the apps are for, right? Like to see if you have physical attraction. You need to be attracted first, and then you get to know it. Yeah. Okay. So now that we know that you're shallow. Keep going. So just to make sure that I really liked his personality and not just his face, I asked him to have like a casual daytime date at a park.

Okay. Because then I can just like leave if I have to. Oh, yeah. You're setting up your exit strategy before you even need him. Okay. That's good. Everyone should feel safe and comfortable. What did you guys do at the park?

We just, you know, walked around, we chatted. We talked about our jobs and how similar they can be because he's a waiter and I'm a nanny. And so he was like, I have customers that like wine and act like children. And I was like, you know, same. Same. Same. And I don't get tipped. Yeah.

I mean, your customers are actual children. My customers are actual children. That's funny. That's funny. I love that. Okay. You guys are bonding. Yes, it was going really, really well.

We were having a great time. And then my phone started ringing. Oh, God. Here it go. I mean, do you answer it immediately? No, I kind of hesitated, but he heard it. And he's like, do you need to take that? And I was like, I'm so sorry.

I do actually need to take this, but I'll be right back. Because it was kind of like a personal thing. And, you know, I just met this man. So I had to go back to my car to take the call. Okay. I mean, if it's an important call, I feel like that's understandable. Yeah. Yeah.

It's different. I thought when Jeff was, you know, talking about this whole day, that you were, like, playing game. on your phone in the middle of dinner. Or like an ex texting you or something, you know, and he saw it. Sure. But, I mean, it's okay to answer, but it kind of depends on how long you're going to be on the phone. Yeah, don't be gone for 30 minutes.

Yeah, that's a good point. It should be like five minutes max. How long were you gone? It was like 15, 20 minutes. And he's just sitting in a park? I know. I'm sure he was playing games on his phone during that time. I doubt it.

I bet he was just sitting there quietly with his hands folded. on the bench. If I was him, I would have called from 10 minutes in and been like, hey, I'm still waiting over here. It's a long time. Afterwards, you go back to the park. Is he even still there? He was there, which was a good sign.

But then I realized I was coming up on the time that I had to be back to my nanny job. Oh. Oh. That was the end of the date? You just sitting in a car by yourself? Well, I mean, I got out. And then, you know, I didn't realize until I was talking to him for like one minute. I was like, oh, I have to leave again.

Oh, oh, no. Well, I mean, you didn't have to leave. I mean, they are just kids. They can take care of themselves at some point. You do have a choice in this situation, and it sounds like at this point, you're choosing your job over him. She's a good nanny. Yikes.

Well, I have to pay bills. Fair enough. But it felt really bad, so I just kind of was like, oh, it was so nice to meet you. And then I, like, gave him a hug, and I left. Oh, that doesn't feel like a romantic. I bet he feels like you don't like him at all. Yeah. He just chose a phone call over him.

Like a fake excuse or something to get out of it. I didn't think of that. He could think it was a fake phone call. That's another thing. Oh. Do you feel bad enough about yourself yet? Sorry, I just realized. I'm just so sweet.

You really don't make you feel terrible about this. You should. And she knows. Good job, Alexis. Did you ever, did you ever explain to him who was on the phone or why it was an important phone call? Like, that would make me feel better if I. New. Totally.

No, just because it's like a really, like, it's really personal. Yeah, Brooke. Why are you trying to dive into her personal stuff like that? That's just extremely inappropriate of you. That's what I do, Jeff. Yeah. I cross boundaries. Yes, on the radio and in my personal life.

All right. Fair enough. So that is kind of an awkward way to leave the date. I mean, what's happened since then? Nothing. Nothing at all? Have you tried to text him or like? I just, I've been too embarrassed.

to call him and he did not ask me out again either obviously. So you haven't even contacted him? He probably thinks you don't like him and you're not getting back to him. He probably thought he's helping you. Like you rejected him and he's like I can take a hint. Yeah. No. Oh my gosh. Okay. So yeah. So that's when I'm going

you guys because I feel like I have to do a big gesture now that it's kind of like been awkward for so long because I don't know what to do so I need your help. Okay. Okay. This seems savable. Yeah. It does seem saveable. I disagree. But let's do it anyway.

We're supposed to just call him. We'll see if he answers. And hopefully we can get you a second date update with Raymond right after this. Hold on. Brooke and Jeffrey in the morning. Second date update. It's Brooke and Jeffrey in the morning. And because our listener Katrina chose to have her first meetup at around noon,

let's look at the comparables of going on a day date versus a night one. Okay. I mean, on a day outing, let's be honest, you're probably not getting any action. Oh. So if you didn't want any, I guess that's perfect. See, my first thought was the lighting isn't as good on a day date. You look at the negatives of it first.

And I know Katrina, you didn't do any drinking this time, but let's say you did. Four drinks during the day makes it look more like you have kind of an issue, whereas at night, four drinks means you're just having a fun time. Hey, you're a fun person. Oh, maybe she has had some drinks. It's a good point. And finally, if you're meeting.

up at night, chances are you probably don't have to leave the date early to go to work. But that's exactly what Katrina had to do after she took a phone call in the middle of their hangout and realized afterwards there was no time left and she had to go.

Which is why she's here seeking our help. Yeah. Overall, not a great review for day dates, Katrina. Oh. Would you switch? Do you wish you would have done dinner or something with him? Instead? No. I mean, I'm happy with the decision. I just wish that I didn't have to pay it at all.

Okay. Yeah. Maybe you should have done a night walk through a park. That would have gone better. I don't think so. With a stranger? I didn't know. Yeah, that's a good idea. I don't know. These are just ideas. We really just need to get to the bottom of this. Call Ray, Raymond, and hopefully he answers and can give us what we're looking for. You can't shorten somebody's nickname before you. I know. I corrected myself. I'll call him Raymond unless he gives me permission. But here we go. I'm going to get another raw. Yeah. Okay, let's see. I'm going. Hello?

Hey, what's up, Raymond? This is... Sorry. Sorry. This is Raymond, right? Yes. Hey, what's up, man? Good morning. Sorry for being overly friendly.

Yeah. Listen, this may sound made up, but I'm being 100% serious when I tell you that you're on the phone with a radio show called Brooke and Jeffrey in the morning right now. Welcome to it, Raymond. Yeah, man. Okay. We're podcast rivals with Julia Louise Dreyfus show. That's true. It's true.

Jeff has been trying to take her down for at least half a decade at this point. Yeah, we're closing in on it. But the thing is, we do a segment on this show that Julia would never do called the second date update. And that's why you called me. Yep. We want you to be a part of it because one of our listeners asked us to reach out to you. Okay. A woman named Katrari.

I mean, yeah. Okay. I like your cold energy. Let's keep it going. I mean, she's kind of the opposite. She's so bubbly and giggly. Yeah, that was very matter of fact. We heard about the date from her, and we're looking to kind of get your version of the story.

Okay, so she told you all about it. She told us that she thought you were really cute, and she had a really good time. She mentioned, like, hanging out at this park. You guys were talking about your jobs and laughing. thing. Yeah, because you're a waiter and you deal with adult children and she deals with real children. And I don't know. I thought that was kind of a funny joke.

Wow. I mean, you guys are kind of missing the whole big thing about this. I mean, maybe it's not important to her. Well, there was one thing that she felt bad about taking a phone call in the middle of hanging out with you. And we kind of piled on her about how dumb that was. Although, she said she didn't really have a choice, though, because it was like, an important personal matter she had to handle. And she feels really bad.

I mean, I'm sure she apologized to you, right? I mean, that's not the big thing that I was talking about. It's not. Would you mind telling us the big thing? She wanted to have a park date. So I get there ahead of time and she shows up with a five-year-old kid. What? She brought one of the kids?

Well, I was like, hey, what's with the kid? but she just says, oh, I'm actually like nannying right now. Oh, my gosh, you did not tell us that. Oh, wait. If I was a parent and I found out that my nanny was going on Tinder dates while they were taking my kids to the park. Oh, my gosh. Is that what was happening?

Yeah, she was like, my boss is paying me $25 an hour, so I figured I'd multitask. Oh. That's not multitasking. But she said she had to leave for work. She didn't tell us that she was at work during the day. She said she had to leave. And where'd the kid go while she was on the phone?

Oh, a lot of questions. Lots of questions. Well, that's maybe the weird. The weirdest part is, like, she got a phone call and then she had to take it. So I'm just watching this kid for like 20 to 30 minutes. You had to watch the... She left the kid with a stranger, no offense. I see

So the kid was misbehaved And that's why you don't want to go No It was just Not cute enough Who does that Who brings the kid on their date? Who goes on a date while they're at work

Like you're a waiter You wouldn't be like Hey let's go to dinner And sit her by herself While you just wait tables around her Yeah It's wild Oh no

Did you say anything? Like I How could you not have I was going to But when she came back From the call She had to leave Like she had to bring the kid home or something.

Oh. Well, here's the good news. Now is your chance to confront her about it. Because you don't know this, Raymond, but Katrina's on the other line. She's always on the phone. She really is. That's a good point you was saying. Never able to give you her full attention.

But now she will because she's there. Wow. Probably with the kid. Yeah. Hopefully not. Katrina? Hi. Katrina.

Yeah, you left out a pretty key detail when you were telling us your story. Yeah. Yeah. I mean, I just don't feel like it's that big of a deal. Oh, wow. No, it seemed like I just left my nanny kid with him. Like, I could see everything from my car. He was at the playground. We go to the playground all the time he has friends there.

I didn't realize he was with an eye shot. Like, as a mom, I am not hiring someone to sit in their car far away from a playground where my 5-year-old is at the park by himself. or I guess with a stranger. Okay, sure. But with all due respect, Brooke, this isn't about you. Okay. Yeah, it's not that far. It's like 40 feet.

And nothing happened to the kids. If anything bad happened, she could reach them. Yeah, thank you. But you know what? We're jumping in with all our opinions. That's not really our place right now. We just want you and Raymond to talk to each other. So go ahead, Katrina.

Okay. Raymond, I just, I want to apologize because I know that our date was kind of like awkward and funky because, I mean, I guess me bringing my kid bothered you, but yeah. My kid. Well, my nanny kid. I mean, I don't want to say his name on the radio. Okay. Now we're protecting him.

That's a good name right now. Raymond wasn't really complaining when I had, like, all these snacks with me. Like, oh. Oh. Yeah, nanny's got snacks. Nanny's have snacks. Exactly. So, like, I gave you string cheese and, like, applesauce.

And it was cool, you know. Like, I mean, I didn't want to go to dinner, but I wanted to, like, you know, still show you that like I can you know we can have fun together and whatever so is he there all right Raymond you got to calm down because you're coming on so strong right here did you eat the kids snacks Raymond she gave them to me the kids food this is too funny it bothered me that I basically got tricked into doing freeze child care and I wonder and I still wonder and I hate to bring it up who was she on the phone with it was the seven-year-old she was still watching from her other name job

She has been on the phone, so I'm still technically watching over you. Okay, okay. I wonder if it was like the mom or somebody. The funny thing is you still are really funny and adorable and likable. You do seem like a good nanny and a nice lady. No, you seem like a terrible name. An absolutely terrible lady that should be fired. Brooke would get a drink with you.

You sound daintable. Like, could you look past that she's just really bad at her job? What do you think about that, Raymond? No I tried That was the best second give I don't know why the timing was great Well I guess I'm not even gonna offer

So Katrina You got your answer Well I'm really sorry Raymond that I you know Disappointed you on our date But you know good luck in that You've got to stop Bring in dates on your nanny job

The kid is old enough to tell his parents You're gonna get busted Brooke, it's not about you. Oh, my gosh. Everybody knows if you're going to do that. You invite the guy over to the house. Oh, no. He can be hands to help babysit.

That's even more scary. Brooke and Jeffrey in the morning. An I-Heart radio experience. You and a pal down under in Australia. At Savannah and the Round Festival. Experience tropical North Queensland in cans and see the roadhammers. and more. With flights, accommodations, VIP passes.

Plus, Great Barrier Reef and Rainforest Adventure Day Tours. And $1,000 cash. Listen to Pure Country on the free IHeart Radio app for at least 10 minutes. Every day you enter is another chance to win. 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. 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. This really just goes to show it's harder to be a nanny now than it ever was before. Especially with Brooke breathing hot judgment down her back the entire time. No, I had a babysitter bring a boyfriend over once.

and you better believe I narked her out as fast as I could to my mom. Okay, Alexis is right here, you know. So, no, but I mean, I feel bad for the nannies. They have so many rules have to follow. They're not allowed to let the kids have too much free time. No candy before dinner. No letting strange men watch them while you're on your phone. I mean, what's the fun in childhood anymore?

Exactly. So if there's any nannies out there listening, I mean, I would tell you you could help pass the time on the job by going and listening to our podcast, but I'm guessing Brooke doesn't want you to do that either. No, that's a good lesson for the kids. Oh, okay, go. Get everybody in listening at Brooke and Jeffrey wherever you get your podcast. And if you ever need help with your love, life, email the show. We'll call that person who's not calling you back. 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. 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 IHeartRadio app,

Apple Podcasts, or wherever you get your podcasts. What's up, fam? I'm sports journalist, R. Chambers. Hey, what's up y'all? It's your girl, Sam Jay. 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. 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.

I'm Nick Tutro. You're probably no more. me from 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 Duturo. 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. you 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 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.