Brooke and Jeffrey: Second Date Update - Second Date Update Classic: First Date Worth The Wait

Episode Date: August 28, 2026

The guy in today’s Second Date was willing to do something that took A LOT of patience, selflessness, and understanding… hear if his sacrifice was worth it in the podcast!See omnystudio.com/listener for privacy information.

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Welcome to the second day podcast. We're so glad you're here. Yes. Especially on a lovely Friday. I'm happier than the other two girls that you're here just so you know. They're like kind of happy. I'm like super happy. It's definitely a competition, Jose. All right, here's your second date. It starts now. Brooke and Jeffrey in the morning. Second date update. What do you think is a good time of day for a first date to start?

Ooh, a first date, I don't know, six, seven p.m.? I was going to go this day. Oh, your p.m.? I like to start mine early. Four am. It's dark, so you don't have to worry about how you look that much. What are you? That's a lot of pressure.

Yeah. Yeah, Jeffrey really gets it in. Some people do a morning workout. He does a morning date. It's nice and peaceful. No one's around to distract you, swoop in, possibly steal your date away. Everyone's in bed. But I get it.

Some people like them later on in the day. Yeah. But one of our listeners, Vincent, says his date started too late. Oh. And that could have been a problem for him. Vincent, welcome to the show, man. Hey, thanks so much for having me. Don't get Jeffrey started.

It started at 6 a.m. Is that what you're saying, Vincent? Yeah. Tell us about when yours started. How did that all happen? Yeah, I mean, honestly, it just took me by surprise. I met this girl Jackie on a dating app. Okay.

I kind of liked how in her profile, like, she had a lot of pictures of her with modern art. Like, she'd gone to, like, the MoMA in New York City or, like, the Dolly Museum and stuff. And I minored in art histories. I kind of liked that, I guess, a little bit. Okay. And it's an easy thing to talk about. Exactly. So is that what your opening line with her was?

Was about, like, Jackson Pollock or something? Yeah, something like that. I actually don't even remember, but I offer to meet her after work and then just got a bar from there or something. And she was pretty chill about that. Okay. Okay. That's cool.

Which was, I thought, kind of nice to be like, okay, meeting you at your work already. That kind of was exciting to me. See, that's why my idea works so well because you start the date and then go to work. Well, before. Yeah. And we're going back to the early morning. I think that this is more happy hour time. She's light to the date because of the morning commute.

I don't know. Was she working an overnight shift? What time was it? No, I mean, I got there like six. Then I just kind of like sat outside of her work for a second because she kept on texting me like, oh, I have like this project deadline and it's going long. And I'm so sorry. How long were you waiting out there? I actually didn't see her until about 9 p.m.

Whoa. What? What did you do? That's a long time to wait. Do you take yourself to dinner? I should have, right? I was starving. No, I mean, I just kept on waiting

and I was like watching TikTok, I guess. Our TikTok at Brooke and Jeffrey, good I mean, I'm insane. Thanks for the show. I love what Jeffrey. Every time there's a moment his eyebrows raise, like, I can plug it. We appreciate you following us on TikTok.

He's like, so what did you two do? Speaking to YouTube, we're also on there. I mean, why didn't she just reschedule? Like, that's crazy. Or why didn't it? Why didn't you? It was just one of those things where it kept on getting pushed. So like every 10, 15 minutes, she was like, okay, I think we're wrapping up.

And then she would apologize. And then she would feel, I felt like she felt really bad about it all. So I kept on being like, no, no, no, don't worry. You know, you work, it's busy. I understand. Like, sometimes I have late nights as well. Totally. She would have felt like she had blown it if you had canceled on the date at the last second there.

She did blow it, though. Yeah. We don't know that. And I'm sure she, I mean, like, when you finally meet her, is she totally fried? Like, she's now been working, like, a 12-hour day, overtime. That's exactly what happened. When she finally, like, came downstairs, she just kind of looked totally exhausted. But she still wanted to go out.

And I said, you want to just call it. She was like, no, no, no, you waited all this time. Like, let's go at least for a drink or something. At least it shows you that she's considerate, bro. I mean, she knows she's late. She's self-aware. See, I don't know. Some people we talk to you have no idea what they did wrong.

It sounds like she, I mean, I have this tendency, too, where you think you have all this time. She just sounds like a terrible time management thing. She shouldn't have even planned a date for that night. So, I mean, did you end up actually going out with her, or was that it? Yeah, no, we did. We got to the bar and we had a good time. And we just came up with it at the time. We were called the arts or not art, where we just, like, pointed at random things in the bar or random light.

But let's talk about the fun parts of the date, though. That is fun. Art or not art? Yeah. That's funny. Okay. No? No, that's just a table.

have nothing else to talk about. All right. What was the most fun piece of art in the bar? I don't know. I kind of like noticed this one kind of schlubby looking guy who was in the corner and he was kind of like doubled over his drink a little bit. And I pointed at that. I was like, do you think that's art?

But like the way that the light was kind of projected from above him, I thought was very artistic and she did as well. Hey, look, it's overweight statue of David. That's a had to be their moment. If you guys bonded over it, then all the power. two of you. So how did the night end? That's all that matters. But yeah, no, I mean, after we played that, her energy still was super

low even after the... Slumped over guy under the fluorescent lights, didn't get her all jazzed up. I think she wanted to play nap or no nap. It's just such a bad night to catch her on, man. How'd you leave it? It kind of just ended super abruptly. Like, I suggested changing venues, or I had a couple friends who were going out to a different bar.

And then she just kept on kind of turning everything down and yawning. And so it was just like a weird ending. She just kind of like hugged me. And then cuddled up underneath the drunk guy. It was like, just leave me here. Yeah, me and him can cuddle. So how long has it been since you last talk to her?

It's been essentially like four or five days. Okay. She may have just been sleeping this. Yeah, she's just in a big recovery nap. If she had a huge project for work, she may have still been swamped. Yeah. Maybe she just hasn't had time. Well, we're going to call her in just a few minutes here.

And we're going to tell her work isn't that important. You need to date. That's a good thing. That's a life lesson. We'll tell her to blow off her work plans and go out with you one more time when we get your second date update right after this. All right. Hold on, okay? Brooke and Jeffrey in the morning.

Second date update. It's the first date that was worth the weight. Oh, I mean, not really. Kind of. Yeah. At least that's what we're hoping for in the end. Right. Because one of our listeners, Vincent, says he sat in his car outside of Jackie's work for three hours.

I don't know why I just assumed he was at a coffee shop or something. He sat in his car this entire time. I thought that's what he said. Oh, I didn't realize that either, actually. I'm going to ask him. Bro, you were in your car? Vince, were you in your car all the whole time? No.

Oh. Oh, Jeff just made it up. God, you made it sound so much more pathetic, Jeffrey. You know what? Let's start it again. One of our listeners, Vincent, was sat in the vicinity of her work place for three hours. Yeah, also sad. For her to finish so that they could hit the bars together.

It didn't make it that much better. He was just watching TikTok videos. See, that's the kind of commitment from a guy that most women would dream of. Your husband wouldn't wait three hours for you to do anything. Wow, that kind of... She's like accurate, but... I wouldn't blame him. I wouldn't wait for three hours for him either.

There's a thing that's being too available. Yeah, good point, Alexis. Committed is the type of guy that Vincent is, so we're all eager to help him. But Vince, first, we got to do a couple prank calls, so if you could just hold on for a few hours. That's very funny. I'm not waiting for this. There we go. He's a demand.

He's learning from his lesson. Put your foot down. That's all we can ask for. Unless they're really quick, and then I can wait a little bit. Oh, no, bro. We're back to the starting board again. You're too nice. I don't know how you have so much free time.

Yeah, what? Do you come? I appreciate your openness for us, Vincent. We're going to do our best here. We're going to call Jackie. You ready? Yeah, super ready. Thanks.

All right. We're looking for Jackie. Yep, that's she. Hey, Jackie. You're on the radio right now with Brooke and Jeffrey in the morning. Welcome to the show, Jackie. Hey, what's up? Surprise.

Oh. Wait, why? That's a surprise sound. Why? Why? Yeah, good question. We do a segment on this show called a second date update. I'm not sure if you're familiar with that, but we try to help out listeners who've gone out with someone recently and are having trouble setting up a second date.

And so you went out with a guy named Vincent who wants to see you again. I did. Yeah. Okay. What do you think about Vincent? I mean He's a very nice guy Oh man nice guys

No it's just like that description always Like if you were to describe a girl It's like oh she's a very nice woman Yeah it's the same thing No one wants to be nice You're not 100% in on Vincent yet Honestly I don't know if I like anybody Oh

Oh you are like that I'm like Bruce So it's not Vincent it's just people Sure Humans. I mean, I think a lot of people can relate to that sentiment. Before we walk down the lonely path with you, can we go back to the date night? Because Vincent says you made him wait for three hours outside of your work.

Yeah. He wasn't complaining about that, but he just said that he was willing to wait for that long in order to see him, and that's a long time for a guy to wait. Oh, man. Well, so I kind of lied. I wasn't actually at work really What?

He said that you were texting the entire time and you're like You had some deadline and it kept going later I know I was I was at home in my pajamas with my cats reading a book Oh that's so rude I was just like kind of hoping he'd just give up after a while and you know Go out Why did you want him to give up like he made this whole plan with it you. Well, here's the thing. I really like the idea of dating and having a boyfriend and going out and

having a great time. But like, in my heart of hearts, I am just a homebody. And like, it gives me a little bit of stress to go out. And I was like, maybe you'll just stop texting and be like, oh, okay. It sounds like you're working too late. Yeah. You just canceled the date. Yeah, you just like, it's way more stressful to lie to someone for three hours and feel terrible about it. I assume you felt bad, right? I did, and that's why, like, I reput on my work clothes. And I drove to my office because he's, like, waiting around, like, a bar right by my office. So I was like, okay, he's going to see me not come out of my office.

So, like, I snuck into the parking garage. No wonder she was tired on the date. she was literally in bed right before it started. Did you have, I mean, did you have any fun on the date? I mean, like, yeah, he's very nice and, I mean, he waited, I guess, and had some fun. And he, like, did this thing, because I liked art and stuff. He did this thing where we played like this. We got the full art breakdown.

Yeah, we got fully versed on all of the arts. Yeah. Overall, what it comes down to, it sounds like, you wish that you could have a boyfriend, but when it comes down to actually doing it and actually going through with the dates you would rather not be doing any of that my dream date is like sit on the couch and watch the movie

we're going to adjust your dream date to being surprised on the radio by a mystery man on the other line who wants to talk to you who's that oh oh you didn't guess it's Vincent yeah yeah I don't think I'd have to spell it out yeah he's there

Listen, I think. I've been here. I'm just trying to process what's got. Oh, man. What's going through your head, Vincent? Are you mad? No, I'm not mad. I'm just more just confused of like, why didn't you just say I'm just not feeling it? That just seems so much easier. Yeah. I don't know. Because I was like, I've said it to people in the past and they've just kind of been a kind of a, so I just was avoiding all of that awkwardness. And I was like, it'll be so much easier for you to make. the decision not to hang out. Oh, then you'll feel less guilty if he cancels. I think dating both people want to bail equally for the night out. Honestly. Vincent, do you want to apologize for not bailing sooner on the date? I mean, yeah, maybe I should have bailed, I guess. Maybe I should have had that sort of like self-respect earlier on.

Oof. I wouldn't go. Don't go too hard on yourself. You know, like, you kept like breadcrumbing you and saying, oh, I'm almost off. I'm almost off. Give me a... And I didn't realize, you know, how... how much someone would want to go out on a date with me, I guess.

Oh, you're worthy of a date. It was a, which is why, I mean, I put my pants on and went out. Wow. Not a lot of women are willing to do that for guys. Vincent, you got a girl to put her pants on instead of take them on. You know? You know, it's going to be the whole rigmarole for you, Vince. Yeah.

But now it just kind of feels like indicative of a larger problem. Like, let's say we do enter in a relationship, you know, or let's say something actually does get tougher in our relationship. Are you just going to shut down like that in a larger capacity? Oh, God. Don't think about that stuff. I thought you were just going to think about, like, what if there's a cool party? And she doesn't want to go with me.

Yeah. I don't know. Like, if I'm comfortable with the person, it's much easier to turn off the loud noise in the outside. But, you know, I don't know people on first dates. It's just like the first, second, third dates are always a little tougher. Yeah. Dating's hard right now. You can kind of understand that, right, Vincent?

Yeah, dating is really hard. I know that because I waited three hours for something. Good job, Bill. Well, they both went through pain that night. And maybe it brought you guys closer together. It's possible. And Vincent, if you heard Jackie, she likes to do stuff at home, don't you maybe want to like snuggle up, watch some Netflix? Dude, both put on your PJs. Some of the best dates I've ever had were all delivery, all on a couch, just talking.

No pants on. Yeah, you could pet her cat and we'll pay for it. No, I do like that. You know, I'm not a total extrovert by any means. I think we have some good momentum here, and that's why I want to offer to send you guys on another date. On us. Or we can, yeah. We'll give you an Uber Eats tab so you can deliver food in.

Like a gift card. Yeah. Maybe like a daytime date just so like it's not after a long day of work and I'm tired and hold yourself accountable. Yeah. Yeah. I see what she's doing. He's going to show up to her apartment, and she'll already be back at work.

Oh, because it's daytime. Yes. So then she'll have to sneak into her own apartment through the back way. I hope not. Through the fire escape. It does feel a little strange. I mean, only say yes if you really want to go, Jackie, please. Yeah, no, I mean, I got to get out of my comfort zone.

And now that you already know my entire story, I don't have to explain it to you anymore. Vincent, she was open and honest. She's a little bit socially anxious when it comes to first dates. but now that you've got the first one out of the way, the second one should be super easy. What do you think? I think as long as it's like an Uber Eats thing or whatever, give it to her and put it in her port.

Oh, you want her to make the effort. No, no, no, no, she's going to order without you. Played yourself, bro. It's a classic Alexis movie. Who wouldn't? Why would you wait? Brooke and Jeffrey in the morning. Today's episode is brought to you by Vinted.

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Plus, from $94 a month, price guaranteed for two years on internet with a two-year term and auto pay credit. Visit bell.ca for details and to check availability. Bell, connection is everything. Man, were you guys thinking what I was thinking the entire call? Like, why wasn't he so angry that she lied to him for three hours and he wasted a bunch of time? Oh. No, not that. I was wondering, did we just get off the phone with the female Jose?

Oh, my God. Because you're so true. You're so right. The idea of having a significant other is obviously amazing. Spot on. But when it finally comes time to have a free night, they would rather stay home, avoid the crowds, order in, stream a show, fall asleep with their hand and their pants are good.

You're so right. How many Fridays does he tell us? I'm like, what are you doing this weekend? He's like, well, you know, this girl wants to go on a date. Yeah. I finally have a Friday night off. I got some time off. I want to stream.

I'm just going to stream with my giggle game. But I want a girlfriend so bad. I mean lonely If you want to skip all that and just marry me, text in the 7-8-5-9-2. Let's have a cute family. I'm sure that'll work out for it. We're accepting proposals now. I won't be at the wedding, by the way.

I've got to take a nap. Fair warning. If you want to get a second-date update, though, you can always email the show. We'll call that person who isn't calling you back. And check out all of our second-day podcast up wherever you get yours at Brooke and Jeffrey. On the new podcast, Solita, we share the messy reality. of traveling alone as a woman. I can wait four hours for the next bus or this random dude is offering me a ride on his motorcycle.

I chose option B. I'm Julie Pinero, and I travel by myself because it's a rare space where I can say yes without asking anyone else first. I'm on a mission to reclaim the word Solita, trading the pity for possibility. Listen to Solita on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. If your bookshelf and your for you page are equally important to your personality, welcome home. Pro Society is a weekly podcast that's part book club, part group chat for anyone who thinks pride and prejudice and love island to serve the same level of discourse. Each week, we're connecting the dots between books, the internet, and pop culture with your

favorite writers, book talk creators, and plenty of overthought opinions. Yeah, I'm obsessed. I'm obsessed. Listen to Pro Society on the IHeart Radio app, Apple Podcasts, or wherever you. you get your podcasts. Hey, this is Hayes Davenport. And Sean Clements. We host the podcast, Hollywood Handbook. Each week, we talk to someone in show business and try to help them with their careers

and see what they have to offer us. Everyone has a good time and no one gets mad at their publicists for letting them do our show. We've had a lot of great guests like Sarah Sherman, Adam Scott, Danny McBride, Ben Stillard, and a lot of other big shots that wouldn't be where they are without us. Listen to Hollywood Handbook on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I survived nine months in captivity, and I've spent my life exploring how other people survive what should have destroyed them. I'm Elizabeth Smart, and these are the Survivor Files.

Every week, I'm with survivors who live through the unthinkable, abducted, stalked, controlled, and nearly silenced. These are stories about what it takes to make it out alive. Listen to The Survivor Files with Elizabeth Smart on the IHeart Radio app, Apple Podcast, or wherever you get your podcasts. Our hometown is not a test tube. 90 miles northeast of Nashville, a battle for the future of America, plays out in one small town.

Developers with right-wing ties have purchased hundreds of acres of land. We need cities on a shining hill. This is Our Town, a podcast about what happens when a small town becomes the site of a social experiment and fights back. Guess you didn't move in

on a bunch of dumb hillbillies now, did you? Listen to Our Town on the Eye. heart radio app, Apple Podcasts, or wherever you get your podcasts.