Brooke and Jeffrey: Second Date Update - Second Date Update: Singles Mixer Shocker

Episode Date: September 8, 2025

One of our listeners came up with one of the CLEANEST & MOST FUN ice breaker questions we’ve ever heard… Hear what it was in a brand new Second Date Update!See omnystudio.com/listener for privacy information.

I just normally do straight stand-up, but this is a bit different. What do you get when a true crime producer walks into a comedy club? Answer, a new podcast called Wisecrack, where a comedian finds himself at the center of a chilling true crime story. Does anyone know what show they've come to see? It's a story. It's about the scariest night of my life. This is Wisecrack, available now.

Listen to Wisecrack on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hi, my name is Enya Umanzor. And I'm Drew Phillips. And we run a podcast called Emergency Intercom. If you're a crime junkie and you love crimes, we're not the podcast for you. But if you have unmedicated ADHD... Oh my God, perfect.

And want to hear people with mental illness, psycho babble. Yes, yes. Then Emergency Intercom is the podcast for you. Open your free IHeartRadio app. Search Emergency Intercom and listen now. Your entire identity has been fabricated. Your beloved brother goes missing without a trace. You discover the depths of your mother's illness.

I'm Danny Shapiro. And these are just a few of the powerful stories I'll be mining on our upcoming 12th season of Family Secrets. We continue to be moved and inspired by our guests and their courageously told stories. Listen to Family Secrets Season 12 on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. It's important that we just reassure people that they're not alone, and there is help out there.

The Good Stuff podcast, Season 2, takes a deep look into One Tribe Foundation, a non-profit fighting suicide in the veteran community. September is National Suicide Prevention Month, so join host Jacob and Ashley Schick as they bring you to the front lines of One Tribe's mission. One Tribe, save my life twice. Welcome to Season 2 of the Good Stuff. Listen to the Good Stuff podcast on the IHeart Radio app, Apple Podcast, or wherever you get your podcast. Hi, I'm Jennifer Lopez, and in the new season of The Over Comfort Podcast, I'm even more honest, more vulnerable, and more real than ever. Am I ready to enter this new part of my life?

Like, am I ready to be in a relationship? Am I ready to have kids and to really just devote myself and my time? Join me for conversations about healing and growth, all from one of my favorite spaces, The Kitchen. Listen to the new season of the Overcombered podcast on the IHeart Radio app, Apple Podcast, or wherever you get your podcast. Hey, it's Brooke and Jeffrey in the morning, and you found our second date feed. Wow, it feels weird saying this.

Normally Brooke would be doing this. I know. But she's out there on the phone with her kids. She's crying. Let's be real. Yeah, she's crying. Happy tears, I think. I don't know.

Her daughter started middle school and it's been waterworks every day here. So it's been a big emotional wreck. Yeah. But she's there. And I have not stopped reading your guys's comments from the second date. Even though it was on Friday, the Euro date, Jose. Yeah. With Norwegian-style dating.

Dude, which I need. to adapt and adopt, I mean, because I did no idea this existed. You know, I don't know that it does exist. I counted in, like, 10 Norwegian listeners commented that this girl has been scammed. Wait a minute. That's okay. That's actually almost funnier.

I know. I love it. So if you haven't listened to Friday's second date, go back and do that. Oh, no. And if you're from Norway, help. I think we have enough Norwegians. I haven't confirmed. Yeah, they have confirmed.

It's not real. But that's okay. Let her live her life that way. Sure. She seems happy. And today, a guy says he has the best icebreaker you'll ever hear. Icebreaker questions. So let us know if it would work on you in the comments or what your answer would be to it.

Yeah. All right. And here's your second day. Or would you do the Norwegian style? Just get right to it. Back to Norway. All right. Your brand new second date starts now.

Second date update. We obviously have heard about people meeting on dating apps. Yeah. Or during activities like a run club or hopscotch. karaoke classes. You do it all at the same time? Yeah. It's really fun, really challenging.

But kind of a more old school thing that's been around and it's making its way back again is singles events. Oh, yeah. You know? I've been really into love on the spectrum, the show, and they do all sorts of speed dating on that show. Cute. And you are doing the singles events too.

Right? No. Oh, no. Okay. But apparently they are still a thing because one of our listeners went to one recently and he needs our help today. His name is Trey. So Trey, hey, thanks for emailing in. Welcome to the show. Hey, guys. Thank you so much for having me. Oh, well, thank you for thanking us for having you. Was this, was this the first, like,

singles, mingle or whatever they called it that you've ever done? No, so I've actually been to a couple of them. I am really anti, like, the dating apps, and I'm much more on making, like, a human connection. Yeah, and it's way harder to lie about yourself when you're meeting people in person. You can still pull it off, trust me, but it's harder. What do you mean I'm not six feet? I'm sitting right in front of you. Okay, so how did it go?

So the last one I went to, it was a little weirder because there's a ton of guys there. And usually it's a good, like, 50-flipty mix, but it was definitely more of, I guess you would traditionally call it more of a sausage fest, as it were. More guys reply to the emails that when they set them up than anything. Sounds like whoever was producing it screwed up. Yeah. Because that's like the whole point of those. Or they hold it at a sports bar.

Yeah. You have to have to be like a cutesy bar. Yeah. If it was that a sports bar, I'd be a little more excited than it's like a regular. Totally. I never thought about the venue playing a role in that. I mean, now you're working at a disadvantage if there's more guys than girls. Yeah, I mean, it can be a little competitive, you know, which is not really like what you want the vibe to feel like.

I don't want to be looking at the time and be like, oh, I wonder if this guy's going to have a better answer than me. Yeah. Okay. Did you come in with like a certain question? you like to ask that's intriguing and good combo starter? Okay, I'll let you guys tell me how good of a question is. So you're familiar that we only

have young Sheldon because Big Bang Theory exists. If you could have any young character show, who would you want to see a young version of? Oh, yeah. That's a great question. Like we're getting the new Harry Potter series about young, young, young Harry Potter. What about the Cosby show? Is that a good answer? Oh, a young

Bill? Young, young. She's actually eating pudding because his mom gave it to him. To see what went wrong. I would not go with that one, Jeff. Okay. My funny answer to that is young George Costanza, because then you still get a little Jerry. Oh, that is funny.

But he's somehow still bald. That sounds like a really good icebreaker. How did the ming actually go? So it didn't go great. Like I said, there's a lot of people. It was just hard to find time to get any FaceTime. with everybody because everyone's just moving so quickly. And at some point, the host of the event came over and mentioned to me like, hey, I really

appreciate you coming out. But then had this, like, very weird, backhanded comment of, I know you're not as attractive as some of the other guys here. Oh, no. Wild. The organizer of the event said that to you. Was it a guy or a girl? It was a girl.

And she was like, I know what a great personality you have because she's seen me at other events. You know, there's no defending that, but if she sees like a thousand daters a week and she's just being, she may just in her head have spoken out loud. Yeah, or if she is also single, maybe she was trying to neg you a little bit. I don't think the... Women do that, right? I think it cold ugly usually makes me feel good. I know. How did you get back in there after that?

My confidence would have been deflated. Yeah, it didn't feel great. Oh, sorry. Not to rush you through this story, but we are going to. be calling somebody you didn't meet a woman eventually right yeah so that takes me to the next part so later in the event a couple of other like girls walked in it was late it was nice because some of the people are already kind of matched so i had a little bit better of an in and that's why i started connecting with step step step she was great we chatted for like 15 minutes one-on-one i asked her out

of course i knocked out which uh young show would you want to her's was young it's always sunny which i think is a perfect day which means she's funny yeah and it's dark humor yeah she likes humor that's great yeah i mean you guys are correct so then we set up a date a week later we met just like really cool wine bar that's near my oh you did me okay yeah i mean had a few drinks but right at like the hour mark she was like well i have to go and just kind of cut it off which caught me up guard because i kind of was locked in for the evening. I was like, great. We hit the wine bar down the road, this really incredible

taco joint that I love going to. I thought it would be like a fun, like, whole night. Yeah, wine and tacos, perfect combination. Honestly, it is. Just because it was right on the hour market, it sounds like maybe she, like, read something somewhere that's like, oh, don't let your date go more than an hour. You know what I mean? I don't know.

Or, I mean, my head first went to, if she's doing these speed dating events with him, maybe there's multiple other guys that she matched with and had a whole... That's not a bad idea either, Jack. It's a common thing to have, like, kind of a rotation, a roster now. And then, like, a big day, we just knock them all out. Exactly. Yeah.

How long ago did that date happen? That was about a week ago. All right. And you ever heard from her at all? No, she hasn't gotten back. And I'm also not someone that's going to, like, triple text someone. Like, I'm going to, you know, I'll give the space to respond. You are self-aware?

That is crazy on this show, dude. Yeah, that never happens. So let's come back. We're going to call Steph for you. try and get you a second date update in the meantime if you like younger versions you can go back and listen to old stuff from our podcast. Here are a little bit younger

versions of us. Younger Jeffrey. We're never older on the podcast, are we? No, we're not. But we'll do it with your second date update right after this. Second date update. If you're just joining us, we've been talking to Trey about his date with a woman named

Steph. They met at a singles mixer where he learns Steph likes the show It's Always Sunny in Philadelphia. Which is why I yelled, yeah, sorry. Yeah, yeah, yeah. So, naturally for their date, he took her out not to an Irish bar, but to a wine bar. I thought you were going to say. I should have been Irish.

No, it's smart. Don't give women everything they want right up front. Make them work for it. Just do a dumpster behind the... Yeah, that would have worked just as well. It would be more always sunny to me. But at the one hour mark, Steph kind of called it all of a sudden, and almost like she was timing the date. Yeah.

So kind of a strange end to it. And, Trey, here's the day. deal. If we are able to get her to answer, you know we're going to talk to her about your actual date and probably about the night you two met. So I need to ask you, is it totally off limits for us if it comes up to tell her about the host of the singles mixer calling you unattractive? Why in the world would we mention that? I'm just saying if it comes up. The date wasn't even part of that conversation. Why would it come up then? Okay, yeah, I'm sure it won't. This is great. Okay.

Brooke is worried. I don't trust Jeff. I don't either, Alexis. Listen, I'm fine with bringing up because I'd be curious to hear what she would say in response to that comment. I don't think you're ugly or not. You don't want to hear, dude. You know we're all together. We're a team on this.

Let's all put our hands in on three. One, two, three, ugly. Okay. You put your hands in and then you're left. Jeff, you didn't even do it right. Dude, I will say right now that there are many people out there that may not be beautiful first meeting, but then they get more attractive. the more you know him.

God, you hear her voice. She doesn't believe that. I do believe that. Yeah, you're rock bottom. Okay, here we go. It's not going to come up. I won't say it. Here we go.

There's a reason why you guys are my favorite show. Oh, God, I hope it's not this. This is for entertaining, I guess. We'll see. Okay, I'm going to dial her number. Here we go. Let's see if stuff answers. Hello?

Steph? Yeah. Hey. I'm sorry, I'm all uncomfortable. Fonz is on the show with us today. That is a reference that no one under the age of 50. It's fine. We're a radio show.

We're called Brooke and Jeffrey in the morning. Staff, are you still there? Yeah, okay. Hi, Steph. Hey. As you can tell, we're a really fun, jokey type of show. but we do get serious a little bit with this segment that we do. It's called the second date update.

Okay. Okay. Has not clicking. Yeah. Explain it maybe. Maybe you explain it. Oh, okay. Well, Steph, you met a great guy who you went out with and now he wants another date and you aren't calling him back.

Who's this guy you're talking about? I'm really bad with names that I forgot to write. Oh, bro. All right. I forgot to write his name down. It's okay. Pass the baton to me. The guy's name is Trey.

That's what I was going to say. Trey. Okay, back to Brooke. Do you remember Trey? Yeah, I do. Yeah, I feel kind of bad about that one. Oh, you do? Oh. Well, we heard about the date that you two went on to the wine bar. And from Trey's description of it, it was a really nice time. So he's a little bit just confused now that there hasn't been a second meetup, no follow-up afterwards. Well, maybe that's why she feels bad. Is that why you feel bad stuff? Honestly, I don't even know if I should be like telling you. about this because it's kind of embarrassing.

I feel weird about it. Oh. It's embarrassing. Is it embarrassing for you, or is it embarrassing for Trey? I guess potentially for everyone. I don't know. Okay. Here's the deal.

Whenever we have listeners on this segment, they acknowledge that there may be some awkwardness, some difficult truths that they have to hear. And Trey just wants to know the honest reason there hasn't been a second meetup, no matter what. Okay, well, I mean, I guess I can tell you. It would really help him out.

Yeah. Basically, I'm friends with some of the people that organized these singles events. Are you kidding me? I mean, just one particular night, you know, they didn't quite have enough people there. Specifically, they didn't really have a lot of women. Oh. He had actually mentioned that about the speed dating night that you guys met, that there was a lot of guys. Then there was like another wave.

Yeah. That would be because sometimes they give people, like, 30 bucks to just show up and, like, kind of mingle with everybody. What? Fill it out. You, whoa. Well, you went on a second date after that. That's true. You guys did go to the last point. Were you paid to go out with him on the second date?

No. No, not at all. It was just the initial kind of speed dating thing with everybody. But I just kept thinking the whole time, like, this continues to go well. We're going to have to have a conversation. about I answered the picture initially and I just feel horrible about that

because I don't want him to take it the wrong way I'm confused though were you interested in him or were you not because it sounds like you went out to the wine bar just for an ego boost is what I'm picking up that was part of it but I mean he's he's really cute he's really nice

anyone would be lucky to like go on a date with him are you sure he's really cute like how cute is Jeffrey it's a good chance me to tell us how cute he is Okay, I'll back off. He's adorable. So where is your head at now, Steph? Because according to him, you're not reaching out to him anymore.

That sends the signal that you're not interested. Well, I don't know. Sometimes I'm just really non-confrontational. And I really, really don't want to have that conversation where I'm like, oh, hey, I was paid to meet you. So then you're never going to get into a relationship with this great guy because you don't want to have a talk about it? We're just paid to go to the event? But initially, that's how they made. like she was paid money to go there and meet him.

And I can see how... Not him specifically, though. No, just to be there. Sure, anybody, but anyone finding out the person they really like was paid to meet them. That's not going to feel good. It is cute. I hear you that you're worried about having that conversation with him down the line

somewhere. It could be awkward. The good news is, we already got it out of the way. Like a band-aid. Wicked it right off. Because he's actually on the other line listening to this right now. No, no, no, no. Yeah.

Please do not say that. to me. I can't not say that to you because the truth is he is. Oh my God. It should be at least. Hey, how's it going, Steph? Trey, I'm really sorry. You had to find out like this. Pretty strange.

I totally understand the awkwardness of not wanting to like mention how you ended up at set event. Obviously, I was there as a participant, but I think whatever the love story ends up being, it doesn't matter the origins. It's more about how it ends up.

Okay. So, Trey, you're not offended at all or put off by the fact that she was paid that night to be there? Honestly, not. That's kind of up to the organizer. I mean, she's got bodies there. However, they get there as long as we're continuing to, like, have a conversation. And it's not all being paid to continue that conversation. If anything, you should be, you should feel guilty, Steph, that you took the money since you met somebody at the event. Oh. You know what I mean? You should pay him $30 to make it even, and now he knows you really like him for him. Right.

I was just going to have her give the money back to the organizer. I was thinking that. You know your friends. You can always send it to us, too. I mean, we could always be 30 bucks. But, Steph, what do you think about what he just said there? I don't know. I just, I enjoyed your company.

I enjoyed talking with you. That's nice. Cute. I just got, like, nervous. And like I said, I was too in my head about the conversation. we were going to have to have. But it's all out there now. Yeah, and I feel some positive momentum happening.

We've got some of that awkward conversation out of the way. And you don't even realize it, Steph, you're really good at conversation. You gave the best answer to his TV show question out of the entire night. We loved it. And that's why this is going to be kind of tricky because I want to offer to send you on another date and tell you we'd pay for it. But then it feels weird. Yeah, and then it's like I'm paying her to show up to the date. I see where we're at.

She, Ben is a charity at this point. Yeah, I'm not going to offer to pay for you guys to meet up, but we will strongly encourage you to get back together. How does that sound? Honestly, I don't want this to be more confused or muddled by money being involved. I'd love for it to kind of feel more organic and genuine. Wow. As far as it money, it's more like Appleby's gift card.

Yeah. Still, though. So, Steph, will you go out with me again? Can we try running it back and doing it again? Aw. Wow. Um, yeah, I mean, I think I'm going to say yes. It's not like a pity yes or anything.

Like, I really would like to see it. You know, that's kind of a backwards compliment, but we'll take it. Well, I mean, this is such an odd way of going about it. It's not like I feel pressure from you or anything like that. Oh. Plus, it's not like she called him unattractive, right, Jeff? Right, exactly. No.

Good. Good. Really good. Nobody ever would call him that. Thank you, Jeff. Congratulations, Trey, and congratulations, Steph. You're both going to meet up one more time, and we're not going to pay for it. My name is Ed. Everyone say hello, Ed.

I'm from a very rural background myself. My dad is a farmer, and my mom is a cousin. So, like, it's not like... What do you get when a true crime producer walks into a comedy club? I know it sounds like the start of a bad joke, but that really was my reality nine years ago. I just normally do straight stand-up, but this is a bit different. On stage stood a comedian with a story that no one expected to hear. Well, 22nd of July 2015, a 23-year-old man had killed his family.

And then he came to my house. So what do you get when a true crime producer walks into a comedy club? A new podcast called Wisecrack, where stand-up comedy and murder takes center stage. Available now. Listen to Wisecrack on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. My boyfriend's professor is way too friendly,

and now I'm seriously suspicious. Wait a minute, Sam. Maybe her boyfriend's just looking for extra credit. Well, Dakota, it's back to school week on the OK Storytime podcast, so we'll find out soon. This person writes, My boyfriend has been hanging out with his young professor a lot. He doesn't think it's a problem,

him, but I don't trust her. Now he's insisting we get to know each other, but I just want her gone. Now hold up, isn't that against school policy? That sounds totally inappropriate. Well, according to this person, this is her boyfriend's former professor, and they're the same age. And it's even more likely that they're cheating. He insists there's

nothing between them. I mean, do you believe him? Well, he's certainly trying to get this person to believe him because he now wants them both to meet. So, do we find out if this person's boyfriend really cheated with his professor or not? To hear the explosive finale, listen to the OK Storytime podcast on the I heart radio app, Apple Podcasts, or wherever you get your podcast.

Oh, what a great wedding toast story, if it ever gets to that point. Oh, I think they're so cute. My friend paid me to meet him. Yes. And then I fell in love. I mean, it is perfect because it's funny, a little self-deprecating. Isn't this the plot to pretty woman? Yeah.

You just don't hear that enough in wedding vows anymore, especially with guys as classically unattractive as he was. Oh, you have to get it out. You finally said it. We said not to say it during the call. Call's over. They're probably free reign. It was killing you, wasn't it?

I did a great job, and you can all thank me for not bringing it up later. Oh, boy. That's the bar. Yeah. If you want to thank us, or if you just want our help, we're available online. You can email the show. We'll call that person who's not calling you back and go check out all of our second dates, wherever you get your podcast at Brooke and Jeffrey.

I just normally do straight stand up, but this is a bit different. What do you get when a true question? Crime producer walks into a comedy club. Answer, a new podcast called Wisecrack, where a comedian finds himself at the center of a chilling true crime story. Does anyone know what show they've come to see? It's a story. It's about the scariest night of my life.

This is Wisecrack, available now. Listen to Wisecrack on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hi, my name is Enya Humanzor. And I'm Drew Phillips. And we run a podcast called Emergency Intercom. If you're a crime junkie and you love crimes, we're not the podcast for you. But if you have unmedicated ADHD... Oh my God, perfect.

And want to hear people with mental illness, psychobabble. Yes, yes. Then Emergency Intercom is the podcast for you. Open your free IHeartRadio app. Search Emergency Intercom and listen now. I'm Dr. Scott Barry Kaufman, host of the psychologist. podcast. Here's a clip from an upcoming conversation about how to be a better you. When you think about emotion regulation, you're not going to choose an adaptive strategy which is more effortful

to use unless you think there's a good outcome. Avoidance is easier. Ignoring is easier. Denials easier. Complex problem solving takes effort. Listen to the psychology podcast on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts. Every case that is a cold case that has DNA. right now in a backlog will be identified in our lifetime. On the new podcast, America's Crime Lab, every case has a story to tell, and the DNA holds the truth. He never thought he was going to get caught, and I just looked at my computer screen. I was just like, ah, gotcha. This technology's already solving so many cases.

Listen to America's Crime Lab on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hi, I'm Jennifer Lopez, and in the new season of The Over Comfort Podcast, I'm even more honest, more vulnerable, and more real than ever. Am I ready to enter this new part of my life? Like, am I ready to be in a relationship? Am I ready to have kids and to really just devote myself and my time? Join me for conversations about healing and growth, all from one of my favorite spaces, The Kitchen.

Listen to the new season of the Overcombered podcast on the IHeart Radio app, Apple Podcast, or wherever you get your podcast. Thank you.