Brooke and Jeffrey: Second Date Update - Second Date Update: First Timers Club

Episode Date: January 21, 2026

The guy on the phone today is a member of the “First timers club.” What’s the first timers club, exactly? Find out for yourself when we do a Second Date Update!See omnystudio.com/listener for privacy information.

It's Ryan Sechrest here. If you love adventure, travel, culture, food, and architecture, there are certain cities you've got to just visit in your lifetime. Madrid tops the list. World-class museums, inspiring art, venture just beyond city limits to discover vineyards and medieval towns and feel like you're adding a second vacation, but those escapes are all part of Madrid's magic. Need another reason? How about the F1 Grand Prix arriving in 2026?

The buzz is real. See what everyone's talking about. at only in Madrid.com. A new year doesn't ask us to become someone new. It invites us back home to ourselves. I'm Mike Delarocha, a host of sacred lessons, a space for men to pause, reflect, and heal. This year we're talking honestly about mental health,

relationships, and the patterns we're ready to release. If you're looking for clarity, connection, and healthier ways to show up in your life, sacred lessons is here for you. Listen to Sacred Lessons with Mike Deloach on the IHart Radio app, Apple Podcasts or wherever you get your podcasts. Hey, it's Joel and Matt from How to Money. If your New Year's resolution is to finally get your finances in shape,

we've got your back. Prices, they're still high and the economy is all over the place. But 2026 is the year for you to get intentional and make real progress. That's right. Each week we break down what's happening with your money, the most important issues to focus on and the small moves that make a big difference. Kick off the year with confidence. Listen to How to Money on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

This season on Dear Chelsea with me, Chelsea Handler, we've got some incredible guests like Kumail Nanjiani. Let's start with your cat. How is she? She is not with us. She. Great, great, great way to start. Maybe you will cry. Ross Matthews.

You know what kids always say to me? Are you a boy or girl? Oh my God. All the time. I know. So I try to butcher it up for kids so they're not confused. Yeah, but you're butching us. It's basically like Doris Day.

Right? No, I turn it to be Arthur. Listen to these episodes of Dear Chelsea on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. This is Dr. Jesse Mills, host of the Mailroom podcast. Each January, men promise to get stronger, work harder, and fix what's broken?

But what if the real work isn't physical at all? I sat down with psychologist, Dr. Steve Poulter, to unpack shame, anxiety, and the emotional pain men were never taught how to name. Part of the way through the Valley of Despair is realizing this has happened and you have to make a choice whether you're going to stay in it or move forward. Our two-part conversation is available now. Listen to the mailroom on the IHeart Radio app, Apple Podcasts for wherever you get your favorite shows. Hey, it's Brooke and Jeffrey and this is the second date podcast.

And today, honestly, like, it's incredible to be part of anyone's love journey, period, right? That they invite us in. But today we've got a guy who has never been on a date. before. Oh, we could be so wholesome, so innocent. Yes, he's 25 years old. It's his very first date and

he called us for help. I don't know if he should have, but... We'll be talking in probably the next five years and see how dating goes for him, you know? Yes. So you got that brand new episode about to start, but first comments. Yeah, Pop-Tartuie said the other day.

This is one of the best episodes I've heard. I listen to you guys every time I'm driving somewhere and this had me dying. I genuinely hope you guys never stop making these. I can see myself being 70 and still listening to this podcast. I hope we're in your guys' lives that long. I'll be 120. Like, so tell me.

Did he have teeth? Did he slide into your DM? That's not even a thing anymore. Yeah, come on, lady. Did he holograph into your mind? Okay, listen, we got a brand new episode starting right now. Brooke and Jeffrey in the morning. Date update.

You know, personally, I like the second date updates where people haven't really been dating for a while and they need to jump back on the horse. Yeah, you know. Or slide back into the hot tub. No time like, wait, the present. Whatever the saying is. I think that's it. Sure.

Put your key back in the bowl. Yeah, exactly. And I'm assuming that's the case for our listener, Sam, because he said in his email, dating is foreign to him. Does that mean he just likes foreign chicks? I don't blame him. Hard for me to read between the lines here, so let's find out. Sam, is it with me?

Yeah. Guys, I'm talking to Sam. He's into foreigner. Sam, can you understand what I'm saying? I don't speak that language. French people don't speak that language either. So what do you mean when you say dating is foreign to you? How long has it been since you went on a date?

Forever. Oh. Wait, wait, no, honestly. Like, have you ever been on a date? That's not, I'm not being sarcastic. No, I mean, forever. This is the first date I've ever been on. Oh, wow. Okay. You're telling us. Oh, that's awesome. You're saying you've never been on an actual date with a woman before in your entire life.

No, I've always wanted to, but at 25, I finally got my first taste and it vanished again. Oh, no. Good for you. I mean, it makes sense. Like, you're 25, like the COVID era, like, really screwed your guys' social lives up, you know, like postponed everything. So here we are. Yeah. So who are we going to be calling here? What's her name? Her name is Whitty. Whitty? Witty, yes. Okay, cool. How'd you meet her? So I'm a graduate assistant at a chemistry lab for a local university. And we had a situation working with this company. They have people come in a few times a week to use her lab facilities and she's one of those people. So I got to know her a little this way. That's good. That's good because you're naturally you learning about each other, right?

I have to know. How long did it take you to work up the nerve to ask her out? I couldn't really pick up that she was interested the first few times, you know, and then she hinted at wanting to get together and then I asked her out. Okay. Oh, that's good. That's good. She kind of stepped up a little bit for you. How did you do it? What was your approach? I mean, I just basically, I wrote on a piece of lab paper, and I wrote, what would you say to a cute guy in a lab coat if you wanted to take you out to dinner? And she said yes. All right.

Okay. This is great, man. This is all going off to a good start, especially for your first date. So where did you guys go? So it was weird because it was actually the same day. She was working at the lab. So we kind of clocked out at the same time And she asked like where are you taking me to

And I realized I kind of forgot about that part Oh You didn't pick a place? Because it was happening right then the day Yeah so we went to this drink place nearby They had an outdoor patio But nobody else was on the patio because it was cold Oh

So you guys sat on the patio in the cold Well I didn't want to complain And I asked the serve if the restaurant had some blankets And... Oh, what was that cold? Yeah, and they did. And I ended up with two big blankets around me while we got to know each other.

Oh, just for you were the blankets. You didn't give any blankets to Whitty? Yeah, usually if they bring out two, it's one for you and one for her. Two for yourself. Well, after I had them, I realized, oh, I should probably offer her one. And I did, and she said she was fine.

Yeah, because you were already snuggled up with them. Buddy. I mean, I know it's your first date, but that's like, all right. At least you asked it at some point. I was like, I was just nervous and I was not thinking straight. That's an interesting look to be outdoors on a patio wearing two blankets on a first date. I know it sounds ridiculous, but I think I made it look cool because I had one like a cape. Oh.

Oh. Like a superhero job. Oh, excuse me. I didn't realize. All right. What did you guys connect about? We do like questions like if you're stuck on a deserted island and you could only bring three things. what would you bring?

Those are good first-day combos. Oh, yeah. I always hook up right after that question. What? I don't want to know what you say you bring then. You mean a bit. Yeah. It really depends on how you answer.

What was your answer? Well, I told her first toilet paper because that's a very underrated commodity. Okay. That's true. Okay. She was like, well, what about food? And I was like, well, sure, you couldn't eat anything, but what are you going to wipe with?

So. You're like stuck on that. defending the toilet paper answer. Okay. Were you guys laughing about it or did it feel like it kind of devolved into bathroom talk? No, it wasn't the whole conversation. It was just she kind of was giving me a hard time about it, like cracking jokes. Okay, that's good.

It was fine. But the date only lasted an hour. And, I mean, it's my first date ever. So I don't know if that's normal or not. Dude, sitting outside in the cold for an hour means she liked you. Yeah, especially, wasn't this after work, too? Yes. Like, that's a long date, I think.

After the drinks were all done, how did it end? Well, I don't know when you're supposed to kiss, so I just kind of sat in my car and waited for her to make a move, but she didn't. That's your job usually, brother. Well, one of my friends, he said that he did that, and he got slapped in the face, so I didn't want to offend her. You're being extra cautious, okay? So what's happened since then?

I saw her in the lab last week, but she didn't talk to me, so I don't know. That's not good. Do you know, is she very experienced with dating? Because maybe she didn't talk to you because she was nervous. She said she had a couple of boyfriends before. Oh, okay. Okay.

I was helpful for you. No. Wait, did she know that it was your first date? Did that come up? I did not flat out say it was my first date, but I alluded to the fact that I don't date often. Okay. Okay. By often, you mean forever.

And I appreciate what you did there. Well, you and I both know that. Yes, we know because we speak French together. The language of love. Yes. And we're going to get her to hop on board the love train. Oh, say that in French, Jeff. We'll say it and get you another day with your second date update right after this.

Hold on then. Brooke and Jeffrey in the morning. Second date update. Two chemistry students walk into a lab. One says, hey, you want to go on a date? The other says only if it's a stable relationship. Stable, like the elements? Yeah, because elements, some aren't stable and some are.

Proton electron ratios. Positive or negative ions? People aren't laughing not because they don't get it. Yeah. Oh, man. The AP Chem students at Sam's College would be going crazy for that joke right now. They would write a way better joke than that joke. I'll tell you, Sam's been going crazy over a woman named Witty,

who works part-time at his lab after he took her out on his very first date ever. I bet he's not going to be able to talk to us because he heard your joke and he can't stop laughing. He's still laughing right now. Oh, I'm sure. He's giving more time to recover. But if you missed it, there were drinks, there were blankets involved. On him. Only on Sam, but there has been a total lack of communication since then, so he needs our help.

Sam, have you recovered laughing from my joke yet? Yeah, I think so. I enjoyed that pity laugh, Sam. That's all good. Hey, you know, this is your very first. first date. So I don't think that you, I don't know, I'm just worried that we're going to get her on the phone and she's going to say something hurtful. Yeah. Ouch. Why would you jump immediately to? She's definitely going to say something that's going to hurt your feelings. Yes. I mean, dating can be hard and don't take that personally. Like, just because you're not a good match with this person doesn't mean you won't be with the next.

Brooke has given up on this before we've started, Sam. So she's saying, get ready for a consolation. Anyone's first time for anything. It only goes up from there. Thank you, Jose. gets me. Yeah, I get you. Sam, do you get it? Yeah, I've prepared myself. And also on the other side, don't be too excited if she says it's the best date that she's ever been on. No, you can be excited for sure. That'd be a good thing. Take your wins in the Navy World, dude. Take your wins. Okay. So are we going to call her or just talk about it? No, we're just going to think of more scenarios of telling you how you should feel when you hear other things. We're just going to go over what if a bunch. Jeff, I was just trying to be kind

to this guy. All right, let's be kind to the listeners and dial her number and see you. if she picks up. Here we go. Hey, is this Whitty? Yes, it is. Who's this? Hey, Woody. This is a radio show. We're called Brooke and Jeffrey in the morning. Welcome to the show, Witty. Hi, good morning.

Good morning. What's this? Why are you calling me? Well, we're doing something on our show. We call it the second date update, where we try to help out listeners who've gone out with someone recently and they're not getting a call back for another date. we try to reach out and figure out if there's a reason why. Oh. This seems weird.

It is a little weird. I think it would be weird to get a phone call like this. I mean, that's understandable. Yeah. It's supposed to be like a really fun segment because of trying to help educate people, especially our listeners, if they did something wrong. So you went out with a guy named Sam. Yes.

I did. Okay. You and Sam met at the lab that he works at? Yeah. We did go on a date. Okay. And I think that's it. That's the end.

The end. All right. Well, is there a reason that you haven't been talking to Sam a lot since the date happened? Because he said you've run by each other in the lab, but you aren't really speaking to one another. Yeah. It was just like a... kind of a weird date. It was just a little

strange. She seemed really nervous. Oh, yeah. Okay. What part was... That makes sense. I mean, because you're a great gal. Yeah, you're a beautiful woman who wouldn't be nervous to go out with you. Sure. What part was strange to you? Well, I mean, their conversation was fine. He asked me, you know,

had I been in a relationship? And I was like, yeah, I've been in two long-term ones in the last five years. Okay. And I just got out of one like six months ago. And then he was like, well, I went to Amsterdam last year by myself. And I was like, oh, okay, cool. Traveling the world. Yeah.

I mean, he's just trying to share stuff about himself, right? Sure. And then he was like, I've been to a lot of places like that. Like, I have experience. Like, he kind of like leaned in. It was like, I have experience. Experience what? experience traveling?

Hmm. I don't know. Like in like these places, I was like, are you like some pervert that just goes to like different red light districts and am, you know? Wait, did he bring up red light districts to you? Or are you just assuming that? He didn't mention red light districts. But this is like right after I mentioned I had two boyfriends.

So we were talking about relationships. We weren't talking about travel. So you read that as Sam is bragging about traveling all over the world going to different red districts and has tons of experience. Yeah. That's how you read it, but let's find out if that's really true. Dude, is that a question we're going to ask you? Well, Witty deserves to know the answer because that's exactly what's holding her back from

talking to again. And I need to tell you, Sam's on the other line of this phone call listening right now. Oh, no. Yeah. He did not pay for this call, just so you know it was free. Sam? Hey, how's it going? Oh, wow.

I said I had been to answering, yeah, I told you that, Woody. That was between you and I. What? Are you confirming or denying the Red Light District thing? Oh, I went through, yeah, I went to those places. I was there. That's like part of the experience. No, it's not, Sam.

No, it's not. You saw it. Did you partake in it as a different story? Wait, no, did you use that as your experience of relationships as well on a first date? Well, I said that because you said you had so many boyfriends and I wanted to say something to show that I have experience as well. Okay. I don't know if we need the details. No, no.

Yikes. I just, I'm totally weirded out by you comparing like relationships with meeting. up with sex workers. Like, it's just very odd and weirded out by you, to be honest. I'm trying to figure out why, but maybe okay.

I mean, I have to confess you're my first date ever. Okay. There it is. That wasn't the time to bust that out. That wasn't like your emergency safe car. That's the one thing that you probably didn't know, Whitty. What do you mean?

How? Is that possible? How old are you? I've never been on a date before. Why not? I didn't want distractions for a long time of my studies, and then now that I'm older, I feel more inclined to do that. I just can't believe that you've gone this far without ever going on a single date.

That's a red flag. That's another red flag. Yeah, I'm just, It's red lights and red flags. I was going to go together. But it's been to Amsterdam before. Like I said, so I do have experience. No, no, no, no.

Don't double down. I know you haven't been on, like, any actual dates before, but a lot of the times, people don't want to discuss their experience until, like, at least date number two. It's not something to talk about. It's something to show later. Let the work do the speaking for you.

Yes. I can totally do that. I don't know if the opportunity is still going to be there after that conversation. Guys, he has experience. He can totally do that. I like the confidence. Yeah. I think it would be better if you were just honest with people and said, hey, this is my first date.

I'm really nervous. I don't know. But do not talk about your experience. Like, yeah. God, American women are just so tight. Oh, my God. It's more of a cut and dry transaction. It's not untrue.

But, you know, this is the part of the call, Whitty, where we would normally ask to send you out on another date with Sam, and we would pay for it. But after all to talk about the Red Light District stuff, I feel like even that is going too far. Well, you're not obligated to do anything. No, that's true. It just doesn't feel right.

Whitty, do you have any interest in seeing Sam again outside of the lab? No, absolutely not. In fact, like, you shouldn't ask out anyone in the lab. Oh. Oh. Wait. Wait, Wendy, have you told people it's allowed? Yeah, well, I am now.

Oh, that's fine with me. I'm, you know, I'm actually kind of proud of it. Oh, no. I can't see. I've been like, yeah, I can't date anymore people at work anymore. I heard you do that. Dryed out. Ran out of people.

Okay. How many times have you been to answer, man? That's a good. Oh, wait, do we want to know? I kind of think you're crossing the line by asking me my second. actual history. Yeah. Come on, Brooke.

How many Red Light Districts have you been to, Brooke? Inappropriate. What's your body count? Inappropriate. Brooke and Jeffrey in the morning. You want to know what my evenings actually look like? Homework questions. Someone needs a permission slip signed.

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HelloFresh. Canada's number one meal kit delivery service. It's Ryan Sechrest here. If you love adventure, travel, culture, food, and architecture, there are certain cities you've got to just visit in your lifetime. Madrid tops the list. World-class museums, inspiring art, venture just beyond city limits to discover vineyards.

and medieval towns and feel like you're adding a second vacation, but those escapes are all part of Madrid's magic. Need another reason? How about the F1 Grand Prix arriving in 2026? The buzz is real. See what everyone's talking about at only in Madrid.com. You know, maybe Sam wasn't quite ready for his first date, but he was definitely ready for his second, if you know what I mean.

He doesn't know how to kiss, can't pick a restaurant, but boy, can he navigate the streets of that red light. like this street. Oh, yeah. So you're a second date type of guy. Yeah. I bet you he could lead a guided tour for the English speakers in Amsterdam. Oh, boy.

Wow. That doesn't mean that he's going to, okay. I won't get into it. That would be hilarious. This girl's going to do this to you? This one does this to you. This one does this to you. And that one does a real special thing.

Yeah, he knows all the deals. But listen, definitely not defending what he said. It's just when you've never been on a date ever before in your life and you're trying to figure out how it works. You have to learn really quick what's good to talk about and what is death not good to talk about. Is that something you have to learn? Isn't this common sense?

I don't know. You would think. It just feels like, oh, buddy. Yeah, I mean, you would think, but no. And now the whole lab knows. Yeah, you know?

They learn, no, just how experienced he really is. So if they have any questions, bring it to Sam. Nothing like a bunch of scientists making fun of you. Yeah. That's rough. It's much better to have radio hosts do it.

Yeah, yeah. Because you can always email our show and we'll call that person who's not calling you back. hopefully help you out with your dating life. Go find out all of our second day podcasts. They're up online wherever you get yours at Brook and Jeffrey. It's Ryan Seacrest here.

If you love adventure, travel, culture, food, and architecture, there are certain cities you've got to just visit in your lifetime. Madrid tops the list. World-class museums, inspiring art, venture just beyond city limits to discover vineyards and medieval towns and feel like you're adding a second vacation, but those escapes are all part of Madrid's magic. Need another reason? How about the F1 Grand Prix arriving in 20?

26. The buzz is real. See what everyone's talking about at only in Madrid.com. A new year doesn't ask us to become someone new. It invites us back home to ourselves. I'm Mike Delocho, a host of sacred lessons, a space for men to pause, reflect, and heal. This year, we're talking honestly about mental health, relationships, and the patterns we're ready to release. If you're looking for clarity, connection, and healthier ways to show up in your life, sacred lessons is here for you. Listen to Sacred Lessons with Mike Delaroach on the IHartRadio app, Apple Podcasts, or wherever you get your podcast. Hey, it's Joel and Matt from HowTo Money.

If your New Year's resolution is to finally get your finances in shape, we've got your back. Prices, they're still high, and the economy is all over the place. But 2026 is the year for you to get intentional and make real progress. That's right. Yeah, each week we break down what's happening with your money, the most important issues to focus on, and the small moves that make a big difference. Kick off the year with confidence. Listen to How to Money on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. This season on Dear Chelsea with me, Chelsea Handler, we've got some incredible guests like Kumail Nanjiani. Let's start with your cat. How is she?

She is not with us. Okay, great, great, great way to start. Maybe you will cry. Ross Matthews. You know what kids always say to me? Are you a boy or girl? Oh my God. That's so funny. I love it. So I try to butcher up for kids. So they're not confused? Yeah, but you're butching it up. It's basically like Doris Day. Right?

No, I turn it to be Arthur. Listen to these episodes of Dear Chelsea on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. This is Dr. Jesse Mills, host of the Mailroom podcast. Each January, men promise to get stronger, work harder, and fix what's broken?

But what if the real work isn't physical at all? I sat down with psychologist, Dr. Steve Poulter, to unpack shame, anxiety, and the emotional pain men were never taught how to name. Part of the way through the Valley of Despair is realizing this has happened, and you have to make a choice whether you're going to stay in it or move forward. Our two-part conversation is available now. Listen to the mailroom on the IHeart Radio app, Apple Podcasts, or wherever you get your favorite shows.