Brooke and Jeffrey: Second Date Update - Second Date Update Classic: High Stakes Higher Stacks

Episode Date: January 5, 2026

There’s one thing a guy can put on his dating profile that will instantly up his chances of matching by 90%... The woman on the phone today saw it on her date's profile and now she wants our help locking him down in a Second Date Update!See omnystudio.com/listener for privacy information.

Hey, thanks so much for being here in 2026. Wow. Crazy. Okay, listen, listen. All right, a little housekeeping. We do have a couple of classics, okay, today and Wednesday. And then our brand new second dates are going to start on Friday. Friday.

I think. But I think we also have a brand new episode on Thursday. Yeah, there will be some new stuff. So just you have to listen every day to find out. Yes, we'd be doing tons of recording and making sure that we've got it stacked for you guys coming up this January. So thank you for being here. Enjoy this. classic, and we always love to start with a comment. Yes, and Liliana said, I just broke up with

my boyfriend, and as I was stressed waiting for a reply, all I could do was listen to you guys, and all I got was an ALR. Not even the full word, all right, just shortened it. Okay. Well, you did break up with him via text, so I don't know what you expect it back. Like, just a thumbs up emoji. True, but New Year, new guys, Liliana. There we go. There we go. All right, enjoy this classic, second date. Date Update. Is it ever a good idea to talk about your other dates while you're on a date? No.

I mean, I don't know. If you're like commiserating and sharing funny stories back and forth. Yeah, that's the convo. I would say the short answer is no. The longer answer, absolutely not. No. Unless you plan to be on with us, because we love to hear the dirt. And I'm just thankful that Jennifer, our listener is on the phone with us today.

because apparently she talked about her other dates on her date. That's so unattractive. Jennifer, I disagree. I admire your class. Welcome to the show. Thank you. You are welcome. I mean, it's not like she's talking about like her ex-boyfriend that she's still in love with, right, Jennifer?

We don't know. That's why I'm asking, right, Jennifer? Right. We were just sharing, like, funny stories. You both were, right? Yeah. Good then. That's okay.

Okay. Well, who are you sharing these stories with? What's this guy's? name. His name was Joshua. Okay. I met him on the coffee and bagel app. Oh, is that still around? We haven't heard of that one.

Yeah. I know about the bangle and the candle app, but the coffee one is a different one. Coffee meets bengal? Yeah. I like that one. Okay. He just looked cute. He had like a dog with him in his photo. Nice. You know, actually, I've heard that guys who have dogs in their

photos get 90% more matches. No way. That makes sense. Can I borrow your dog? Brooke, I need your attention here. The whole point is that you can actually keep something alive and care for something outside of yourself. That's the attractive point of it. Women are not going to be able to tell if it's your dog and how well it's taken care of as long as it's in the photo. Just Photoshop one in.

They're going to know after date one, Jeff. Or put a little neck brace on it like it is sick. All we're trying to do is accomplish. Not a sick dog. You don't know your dog's sick, Jose. I just want the trick, guys. Could you determine his dog's health from the photo? Jennifer?

It definitely looked like a healthy, cute. Oh, this is what you're talking about right here. You don't need to sick dogs. I see what you're saying. Okay. Now, take us to the date with Joshua. So I wanted to make the reservation. I said I would make it.

Is there a reason for that? I just in particular, like, I love food. I love eating out. I could relate to that. If you're like, I have my favorites. Let me pick the spot. Love food. Certain tables.

You like all the things. Yeah, so I called, I made a reservation, but when we got there, they had lost our reservation. Oh, no. Yeah, so I guess I should have made it online. Did that, like, throw the night off? Did it make you upset? I wasn't upset. Like, they apologized, but they were just, like, overbooked. Oh, no. That's rude.

Yeah, it sounds like it's a popular restaurant. I know, and there's only two of you. It's like, can you squeeze us in somewhere? We'll sit at the end at somebody else's table. No big deal. Literally make a table for them. We'll eat in the alley back behind the restaurant. If I get the good food, Jeff, absolutely. Totally. It totally turned out to be a good thing because we ended up just wandering around the city.

And, like, we ended up getting burgers at a takeout place and just talking about our bad date experiences. Oh, you turned into like a bonding thing. So you lumped this experience as to one of the many bad date experiences that you've gone on? No, this was just like a. a little bump in the road compared to, like, one time this guy Venmoed me, like, $2.47 for half of his appetizer. Oh, my gosh. Venmo requested you.

Wow. Yeah. Oh, that's like, you're getting paid for it. He's giving you money. I was still offended at the first part. I'm sorry, $2, bro. Okay. Okay, so you shared stories like that with him.

Did he share stories back with you? Joshua did? So he said he had, like, a date who brought. brought her mom, and the mom was, like, critiquing his posture on the bill. Oh, that's right, honey. Sit up straight, honey. Sit up. Oh, my gosh. Pull your shoulders back.

I actually think that's some nice feedback. He probably would have done a bit from it. Jeff, you'd be doing that on the date. Excuse me, you're slouching a little. So, okay, now this is a way to be like, you're actually way better than a lot of the dates that I go on. It's supposed to make him feel good. Yes.

Like, we were having a great time, just, like, laughing a lot, and it was just, like, fun. And anytime you have, like, a shared experience, whether it's like a bad day or anything, it can bring you closer to somebody. Totally. But this wasn't a bad day. No, I know, but they're both commiserating over the same thing. They can't. Oh, okay. Yes.

They have to adapt. Gotcha. So how long did this go on for? Like a couple hours. Okay. Neither of us had, like, planned anything after. So he just, like, walked me back to my car. And I'm not used to, like, a short date like that.

Where it was just like... Do you expected the day to go on longer? Like, did you want him to invite you back to his place? Like, what are your expectations there? I don't know about that. It's just like the vibe was so good. He just didn't even attempt to do anything else. Okay.

Like, maybe he's just playing it cool, you know? Like, sometimes if you go out on top, you end it on a high note. Yeah. It obviously leaves you wanting more, so he did something right. Yeah, he's playing it so cool that he's not even calling her back anymore. Yeah, I guess that is playing it cool. Oh, that is really freezing. We're beyond the cool part.

We just want to help you figure out what happened. Okay, Jennifer, maybe the burger was bad that he ate. That's all it is. It was a street burger. Those are the best kind of, yeah. Yeah, but it is risky. So let's just call him, and we'll get your second date update right after this. Second date update.

Our listener, Jennifer, is the perfect example of when life gives you lemons, turn a them into lemon drops. Oh, yeah. I don't think they, I mean, or burgers. Well, yeah. Yeah, whatever it is. Because her dinner reservation fell through, the restaurant overbooked. So she took that and turned it into a fun night of wandering the city, searching for street

burgers, and talking about previous bad dates that went even worse than this one did. And her date, Joshua shared his worst dates, too. So it really actually bonded them together. But, Jennifer, how long has it been since that night? Yeah, it's been like a week. Okay, and you haven't heard anything? No, and I've sent, like, some text messages and nothing, radio silence. Oh, no.

Okay, so you're definitely being ignored. Thanks for the silent shout out, by the way. Have you tried sending him a photo? Because if he doesn't respond to that, then you know you're in trouble. A photo of what, Jeff? You know. Of anything. No, no.

Don't do that. Don't ever do that. Don't listen to their advice. That is terrible advice. You could send him a photo of me. No. If he's a fan of our show, he would definitely respond to that. Wait, do you think he's mad that she was talking about our other dates?

Now you want her sending pictures of other guys to him, Jeff? I'm just saying if she does and he doesn't respond, then you really know something so. That's the final pass. I think she knows before the picture, Jeff. All right. She's not an idiot. Brooke saying we're not at rock bottom yet. Let's wait until this call happens and see where we end up.

What is happening to you today? Jennifer, any last words before I dialed. these numbers or any last pictures for jeff that you want to send either way yeah i just can't believe i'm half to do this yeah i have to do this had to call us we're the last resort for people that being said with jeff being in a weird mood you want to call back tomorrow this may not be a good call well we'll see we'll find out you're right we're already here let's just go through with it how bad could it get all right let's do it you tell us jill i'll tell you about some of the worst second date updates we've ever done and that'll make you feel better about it hold on

Just call. Okay, here we go. Hello? Hey, is this Joshua? Yeah, this is. Hey, man, this is a whole radio show is calling you right now. We're called Brooke and Jeffrey in the morning. Hey, good morning.

That was a lot. He came in real hot there, Josh. How are you doing? It's Joshua. Oh. Sorry. I'm married to a Michael who hates Mike. I get it. I apologize. I'm sorry that my host is trying to make this segment all about her and her marriage. But we are...

I'm trying to say I understand. Okay, we get it. The real thing that we're interested in, though, Joshua, is you and the date that you went on the other night with one of our listeners named Jennifer. Yeah. Okay. Yeah. Do you remember her? You know what I'm talking about. Yeah. I remember her.

Yeah, it sounds like you guys had a really fun night together. Why do you know that? Great question. Oh, yeah. Because that's how this segment works. It's called Second Date Update, and we spoke to her about your date, and she's a little bit confused about why she's not getting a call back for a second meetup. Really?

Yeah, she said that? Yeah. Yeah. She said that she had a great time with you. It sounds like you guys laughed together a lot. Yeah. Is that not accurate? No, it's accurate.

She's like a really nice person. She's cute and everything, but your words are saying nice things, but your tone is saying something else. Yeah, it's like, really? The, huh, wasn't very good. Well, I don't think I know how to say this, but I just don't think I'm the right person for her, you know? Uh-uh. We don't know because she, I mean, you don't get to decide that, right? That's what she gets to decide.

Yeah, the woman gets to choose who you end up with. You don't get a choice. That's her choice, right? And she obviously thinks that there's definitely something between you, too. if she's calling us. Yeah. Yeah, definitely her choice. Okay, she's quiet again.

Something's going on. Like, can we get your take on the date? Did you feel a connection with her? I don't know, man. Like, we're wanting different things. I don't know if you know what she's in what's called stacking. Stacking? Stacking?

Oh, like the Cups thing where you do it in competition? Oh, yeah. I mean, serious. I bet I doubt her for the long time. The Anna Kendrick song? Yeah. No Okay, so we don't know what that is

Yeah, what is stacking She said she used to stack Which means like have three to four day tonight Wait per night That sounds exhaustive Yeah, that is impressive Is it back to back to back to back to back Or all at the same time?

I don't think it was like at the same We didn't really get into it But like I don't know To me I just think it's kind of rude to say Like I miss stacking Oh she says she misses it Yeah she literally said she misses it.

So, I mean, I could see, like, I would interpret that as, oh, you wish that you were out with someone else right after me. Like, that wouldn't feel good to hear. I could understand that. And that's why I took her to her car when we finished her burgers. Is there any way you could have, like, misunderstood her? No, I don't think I did. He was, like, looking back on it fondly.

And it was very real to her, and she was very, you could tell. Okay. I could totally understand that. It doesn't mean she's doing anything wrong, but it doesn't rub you the wrong way. It doesn't seem like she likes you a lot. Yeah. We kind of all see where you're coming from. I wonder if Jennifer sees it the same way, because she is on the other line listening to this.

Jennifer, if you're on the other line with another morning show too right now, stacking shows, I'm going to be mad. That's just right after us. Oh, that's true. She's good at timing. Jennifer? Hey, Joshua. I didn't think you would be so offended by what I said. So you, like, you said this whole thing up?

Like, you're on the phone here and you called him? Yeah, because I was so confused. I was like, I thought we had such a good time. But I guess it's because I said I missed stacking, which I was just, I mean, that was just a fun time of my life. Like, it's not something I do anymore. I want the same thing you want, which is a relationship. But you miss.

It was fun. It was a fun time. It just feels like maybe that's a conversation you have with your, like, best friends. Yeah. Like, I miss my hope baby, girl. Yeah, that sounds like someone who's never stacked before saying that. Well, it is. Because how could you ever, like, be invested enough to find out if you were interested in someone,

if you were just constantly thinking of the next person you were going to see? I hear you guys talk about this all the time. And Brooke, you've said it's okay to date multiple people to find out who you like. That's true. It's contradictory to what your advice always is. You said, get it in as many times as possible before it's gone forever. That's not what I've said. But I think that dating lots of people is great.

It's just like if you're going to ask someone to give you their evening, you also have to invest not just being there, but like your presence. Like how can you be present? Well said, Brooke. You should have brought her presents, dude. I gave every guy I was with an hour and a half. I was fully present in the moment. And I was not thinking about the next guy.

I gave him that time fully. I almost missed my next day. I mean, it worked for her. She had a boyfriend after that for years. I mean, that's how you see it, Jennifer. But clearly Joshua sees it a different way, right, Josh? Owa. I don't want to mess that up.

I see it like that's your default setting. So I think the anomaly is you having a long-term relationship. And that's what I'm looking for. It's a thing. I mean, that we're looking for the same things. That's what I want. That's just something that's in the past. And by no means did I stack that night when he took me to my car.

I was not seeing another person after you. Guys, that's actually cute. Because she said not makes me think she did. Yes, how I feel is. No. That's exactly how I'm just a dumb guy. I easily am tricked. Not that night, but the next five nights she stacked.

That's different. Brooke, you're supposed to be on my side. Yeah, well, you said. dumb things on a date. I don't know what to talk. I mean, the thing is, the thing is, Joshua, she's on the phone with us. She's put in a lot of effort to see you again. So, I mean, maybe that's proof enough that she's over her old ways. And that's why I would like to ask you, Joshua, if you'd be willing to meet up with Jennifer one more time, and we would pay

for it. And the next date, and the next date, and all the stack dates after them. All the different guys. Just you, though. No, I got the ick. I'm sorry. You got the end. Oh, I can't fix that. Oh, no. Okay, Joshua, do you realize no one says no to me? Oh, that's why she can stack.

Oh, God. That's not true anymore. Yeah, no. Fine, it's his choice, whatever. I'll just keep stacking. Wait. I'll stop this weekend. You said you didn't want to do that anymore.

All right. Well, it makes me happy. It's fun. I'm feeling sad now. Yeah. It's going to get me out of that fun. You need a small army of men back to. back to back to back to feed you.

Yes. That'll make it better. That's where true happiness comes from. He's a single, but okay. Brooke and Jeffrey in the morning. Okay, new year, fresh start. And honestly, I'm starting with dinner. This year, I'm being smarter about where my energy goes.

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Waste less. And for the first time in a long time, I actually look forward to dinner. Get your fresh start right now and get 50% off your first box, plus free sides for life, with Hello Fresh. That's right, free sides for life. Go to Hellofresh.cate and use code Yum50. That's hellofresh.cate. Code Yum 50. All right. So no second date there. Jennifer has hung up. She's not on the line with us anymore. But Jennifer, if you're listening out there, I just want to say, I know you're probably disappointed with one person on this show who didn't support you. But the rest of us here have your back. What? I know you're looking at me, Jeff.

Listen, it's not my fault. She's like, I just really miss dating lots of men at the same night. I mean, no one would feel special if you said that to them. But you understand where she's coming from, right, Brooke? You miss it, Brooke. I have never had multiple dates in one night. Wow. I could not pull that off.

Remember, she used to tell us how good of a liar she was. Yes. Brooke unstackable is the definition we're going to. They call her, Brooke, one at a time, fuck. There's no lie told there. It's so boring. The good news is we've got dozens of guys on the text board who are DTS and down to stack whenever. So, Jennifer, you stay positive.

Yeah, we don't like those. That's weird. It'll happen for you, Jen. And if you're into stacking videos, you can always watch a bunch of ours on YouTube. Got all of our second date updates on there. You can like, share, and subscribe all of it at Brooke and Jeffrey.