Brooke and Jeffrey: Second Date Update - Second Date Update: Vacation On Me

Episode Date: October 16, 2026

Kyle made ONE SLIGHT adjustment to his dating profile and he ended up matching with a woman he calls “The real deal.” So why does he need our help? We’ll figure it out in your Second Date Update!See omnystudio.com/listener for privacy information.

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occasionally different opinions, and at this point in my 50s, I've lived it all. Now in my 30s, being the founder of new shoes, good taste is my business. Listen on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I'm Lacey Mosley, author, actor, stand-up comedian, creator, and host of Scam Goddess Podcasts. The True Crime Comedy Podcasts all about robbery, fraud, and those who practice it. Each week I bring on an amazing guest. Ooh, I scammed them. What?

I can talk to you for an hour. You're a generational yapper like me. That's why I had to make yapping a job. And now you can catch full episodes of my show on YouTube. Start listening to Scam Goddess on the IHeart Radio app, Apple Podcast, or wherever you get your podcast. I'm Hamza. And I'm Martin. And we're the hosts of Out of Character.

The best podcast in the world is what they said. Wait, they said that? Yeah, yeah, they said that. The best podcast with two best friends who jabber and talk about topical, trendy, funny stuff, give our input on it. That's what you've needed, I think, up until now, listener. Listen out of character on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Sometimes I just feel like a burden.

You're a bird. You fly. You're a Martin. And we are out of character. Out of Character podcast. Dude, who messed up the clip. There are thousands of podcasts that can tell you how to better yourself. Get Worse with Kyle Pruh is not one of those podcasts.

So if you're interested in getting thinner, going to therapy, starting peptide, setting boundaries, taking supplements, making your better getting closure, then I would humbly recommend other podcasts. If you're interested in blackmail, love bomb and cloning yourself or getting revenge, then we've got a little something, something for a dastardly individual like you. Listen to Get Worse with Kyle Pruh on the IHeart Radio app, Apple Podcasts or wherever you get your podcasts.

Starting your Friday with a brand new episode. Thanks for being here on the Brook and Jeffrey's second date podcast. Yeah, we appreciate you. We do really appreciate you. And what do we got on comments before we get to it? Yeah, Jenny Jen said, Brooke and Jeffrey is my comfort show, especially if the content is super uncomfortable. Hey, there you go.

How is it your comfort show in the middle of uncomfortability? I mean, I think the opposite works. Yeah. Okay. It's like, I hope today makes you super, super uncomfortable. Yeah. Will that you sleep well? Actually, Alexis, it's not going to work today.

What? Yes, we have real romance on the phone today. Okay. Nice. I say yay and ash and booze. The one time I say it's going to be super uncomfortable. No, this is so sweet. I'm so excited for you all to hear it.

It's going to start right now. Brooke and Jeffrey in the morning. Second date update. What's the first thing that comes to your mind when you think romantic date? Oh. Like candles or maybe flowers. Fancy food for sure. Jose Mentssela light or maybe moonlight.

God, I look so good under any dark lighting. That's why I love those things. Or police flashlight. No, the red and blues aren't as sexy. I mean, obviously, if there's a police flashlight, you shouldn't have been doing what you were doing where you were doing. Oh, one of those big flashlights. We had high school in the back of a car again, Jeff? It was probably worth the 48 hours of jail time.

And I don't want to screw things up here and mislead anyone because our listener, Kyle, did not go to jail. Oh, good. But he did say he tried a unique romantic gesture. And I'm curious what it was. But first, let's welcome him to the show. Kyle, how you doing, ma'am? I'm good. I'm good.

Thank you all so much for having me. It is incredible how many of these start with. He tried something romantic on a first date. You know? Well, you ladies want us to try, and then we do, and now look where we are. Well, it feels like there's a miscommunication in this back and forth. It's usually what they like. Well, to be honest with you, I wish I could have gotten to a first date.

Wait, what? You didn't even make it that far. Hold up. Why did you not make it? What happened? Okay, so I met this girl, Sandra, met her online. And I was on the apps and stuff for a long time in my own city. And I felt like I really wasn't having any connections.

I wasn't meeting anybody. So I was like, let me just try another city. Let me just try, put my location somewhere else and just see if something happens, you know? Does that, okay, I have a question. Is that like a location? catfishing. Like you think that you're meeting someone in your hometown and then you're not? You can do it like that, but you can also put it in travel or passport mode or something. So it's apparent that you don't live there. Okay. But you can also be sneaky.

I was not being sneaky. I was very clear with where I lived and what I was doing. Okay. Okay. So she knew that you were from a different area, but you still match together? Yes. So we start talking and it's great. Okay. So can I ask like how far of a distance. Can you guys drive over a weekend and meet up or is this a flying? It's a plane ride. It'd be quite a drive. Okay. So I can maybe understand why you haven't had a first date. I mean, yeah. Yeah. Logistically, it's hard to coordinate when you have to get plane tickets in order to see each other. Well, we had been talking for a while, probably like 10 days, I guess. And I don't know. I just had this feeling. I just really wanted to meet her.

And I offered this idea. I floated it. I was that, hey, would you be interested in maybe flying out to see me, I'll pay for the ticket, and we meet up because we had been talking a lot. Okay. So can I ask, is this the romantic gesture offering to use your airline bonus miles in order to fly her out to meet you? Oh, yeah. I sent her a picture all my points. Oh, no.

No, it's part of the romantic gesture. Okay. Wait, she agreed? She said she would with one caveat. She wanted her own hotel room. She didn't want to stay with me, which I totally understood. Totally fine. It's better for both of you.

Oh, yeah. Honestly. Yeah. Motel 6 has a great deal, by the way. It's like an insurance, though. Okay, so I'm just going to assume that you're on the phone with us right now because she never ended up flying out. You would be wrong. Oh.

She did fly out. And before she flew in, because I paid for the room, I went up to the room before she was there. And I, um, this is, this is the romantic gesture, kind of the biggest part. Please don't say flower petals or rose petals. Please. Oh, no. No, no. So we had been talking at that point for maybe, I know exactly, 34 days.

Uh-huh. So I wrote 34 little notes for her. Each one was something that I liked about her. Oh, that's a lot. I was hoping you just got her favorite snacks. Yeah. That's all you really want when you land from the airport is someone with snacks. I mean, I will say I love a good love note, but I love them from, like, my husband.

It's someone I've met in person before. Yeah. What are 34 different things that you could write about someone that you've never met in person before. You just feel like I like that eyelash? I like that I lash. It's a good point, Jeffrey. It's little stuff. You know, you're just talking to somebody and then you find yourself thinking about the thing that they said. Like, you know, I like how much you talked about her family. How much she, you know, how fondly she talked about her friends. I like. It's a sweet gesture. I mean, if she's on the same page as you, right, then she's probably

super excited about it. Totally. But it is a big risk that you're taking on the very first meetup. Yeah. Did she see the 34 notes? She like it? She did. She called me afterwards, and she told me it was so sweet. Okay. Did you pick her up at the airport, or had you not seen her at this point? I did not pick her up at the airport. Okay, see, she, yeah.

Guys always get the gesture wrong. The gesture's picking her up at the airport with snacks, not going into the hotel. Yeah, it wasn't good enough that you paid for her flight and for her hotel stay. Yeah, Alex is like, uh-uh. Where are you? She does have a point, though. That's more personal, right? Yeah, it's just putting up notes and being like Uber or see you.

So she called you or she just texted you once. She got to the hotel room. She called me and she tells me, thank you so much. But I'm really tired for my flight. Instead of going out tonight, you think we could go out tomorrow morning. I kind of just want to turn in, you know? That's, I mean, understand. Well, you know when you fly, you know, like, you don't look good.

No, if you were flying across the country for a guy that you're so excited about, you want to see him as soon as possible. That's when you put on makeup at the airport. You land. You're like putting it on before you come out. You're like, yeah. But what about time zone? Like, I don't know the difference.

Like, maybe she landed. and now it's three hours later and she feels like she's... Three hours isn't enough to go to bed early. Nap on the plane. Geez. But what time did she call off the meetup? Yeah. It was only like seven.

Oh. Seven. It was around seven. So it's kind of, I thought it was kind of early, but also I don't know what her flight was like. Like sometimes people are more drained than other time. Yeah. So you were supposed to meet up with her the next day and then what? Yeah.

We had the plan to meet the next morning for breakfast at the hotel. Okay. And I'm there and I don't see. her. And I'm thin for a little while and she's not coming and then I go to the front desk eventually and I ask and they tell me that she has checked out. What? Oh no. Without saying anything to you? Yeah. She hasn't responded to my messages or picked up at all. And at this point I'm like, I just would like to know kind of what happened. I would just try to take advantage of a free vacation. That's what I'm in a fun city. Checked out of the hotel. You would keep the hotel for a couple days, right? I'm hoping that you

live in some terrible city. That's not fun if people would want a vacation to. Nothing to do there. That would take her using you off the plane. Yeah. But we're going to find out exactly what's going on with Sandra. When we come back, we'll call her and try to get you your second date update right after this. Hold on. Brooke and Jeffrey in the morning.

Second date update. Could you imagine meeting a guy online, bonding with him for 34 days, then he pays for your flight to go meet him, puts you up in your own hotel, and leaves notes of all the little things. that he admires about you. Wow. But he doesn't even have the decency to pick you up from the airport himself. Oh my gosh. That is such a misstep, Jeff. Yeah, I would have left too.

After I rated the mini bar, of course. You just hope that more guys would be thoughtful in this world, but apparently they're not. Dude, but can you imagine walking into a room with a guy that you've never met and everything you've ever said to him is written on sticky notes all around you? I know. A guy that listens to what you say and remembers them, disgusting. It feels a little like the start of a horror film.

Yeah. And in your room, he's been in now before you were there even and, like, put it up. Like, wearing the camera. A guy that makes sure that you're taken care of, I agree. Disgusting. She's like, hi. He's like, I have a notepad. I knew you were going to say that.

That was there. And we're just describing Kyle's fly-in date after Sandra did fly-in and stayed the night at the hotel he paid for. hadn't even seen him yet, and then she didn't show up for breakfast the next morning, and it already checked out and left. She'd also canceled dinner the night before. Yeah. But that's because I still feel like she was jet lag. That's nice of you.

Whatever's really going on. We're not sure the actual reasons why. That's why Kyle has reached out to us to try to figure it out. Yeah. Kyle, did I miss anything there from the recap? No, no. I take issue with some of the interpretations of how some of the things could have been perceived. But, you know, that's why I'm here to figure out the truth.

I don't think your intentions were maybe what the perception was, right? Like, there was definitely a miscommunication between you two, I think, on that front. Yeah. Yeah, I guess so. I don't know. I was afraid that maybe she thought I was in the closet. Like, you know what I mean or something like that for a second? I'm trying to read by what you meant I'm in the closet.

I know. I think I'm going to move on from that. Everybody's minds go to what their mind is closest to. Sure. I don't know. The non-physical closet is a lot less scary. Yeah. I also go to dinner.

Yeah. But either way, whatever the reason is, hopefully Sandra can give it to us if she answers the phone because I'm going to dial her number right now. Let's do it. Hey, is this Sandra? This is she. Hey, Sandra, this is a radio show that you're on right now. It's called Brooke and Jeffrey in the morning. Hey, Sandra.

Hey, good morning. Hello. Hi. I just got noticed how this is going to be perceived, too. Yeah. That's true. What's up, guys? I'm really glad that you answered.

Because we're looking to get some clarity for one of our, thank you, Brooke, for one of our listeners that you went out on a date with. Well, you actually didn't go on a date with him. That's what makes this so unusual, because this is called a second date update. Ah, all right. Sounds like you might be familiar with what that is. We're basically trying to help out our boy, Kyle, who told us that you two had planned a meetup. and the meetup never really happened. Yeah, not really ready to talk about this.

Okay. Okay. Well, listen, we don't know what's going on in your life right now, but I do know that we have a guy who put a tremendous amount of energy into trying to set up a meeting with you. He sounded like he cares about you a lot. And after talking to you for a full month, he flew you out to have that face-to-face interaction, but now he's left completely in the dark

wondering, did I do something wrong? Like, did I scare her off? Like, he has no clue. His intentions definitely weren't to freak you out. Yeah. Yeah. Is that what happened? Did he creep you out? You could just start with what it was like walking into the hotel room. So, yeah, I don't know if he told you this, but he left me 34 notes that were. Oh, cute, right guys? She said thoughtful. Yeah. Tell us more about how you felt about the notes.

Yeah. So they were seriously the most thoughtful thing. Like, it seriously touched my heart. You love to hear that. We were really worried that was the moment that, like, freaked you out. But you took it in the way he intended it to be, right? Yeah, absolutely. Okay.

Okay. So then it's because he sent you an Uber to. the airport instead of picking you up in person. It must be that thing. No, it wasn't bad either. I honestly, to be completely transparent, I haven't dated in a long time. All right. Are you just out of a fresh relationship?

So actually, five years ago, my fiance passed. actually so. Oh, I'm so sorry. That's terrible. Yeah. So like it's taken me a while to get through that time. And I've gotten on dating apps and stuff, obviously. And like he's definitely the first guy that I've like maybe I actually saw the potential

of from, you know, seeing how just how he treated me, flew me out, got me my own hotel room. like then the notes and it's just like it's not too good to be true it's just it's so good so I saw the reality of like really starting something new and like I freaked out right right right and I feel very bad I feel bad for the way I handled it would you prefer if we find somebody like one of our listeners who doesn't treat women very well yeah I don't think that's it absolutely not all right So it wasn't like he did anything wrong. It was just you had your own hesitations about restarting romantic life all over again with a new guy.

Enter in a new city, not your house. And all of it. I can understand why you would hesitate to start that way with Kyle or even tell him the situation. But you've already taken half of a step there because you don't know this. But Kyle is actually listening to this conversation on the other line right now waiting to talk to you. In like a romantic sweet way. I feel like a lot for her. Are you okay?

Yes. Kyle, are you okay? I am. Hi, Sandra. Hi. First, I want to say thank you for telling me. She didn't tell you. She told us, but yeah.

Yeah. But you heard it. Well, no, but that's why I got to say thank you for not knowing that you were telling me something very personal. Sorry, I don't mean the joke, but I was just so nervous that I did something wrong. And to hear your perspective, I just want to say, I didn't mean for my gesture to put any pressure on you. I know it's a lot, but I don't want you to think that I expected to start anything that you weren't ready for no matter what your situation was. So I'm sorry.

You're so sweet. So thank you for one acknowledging and then listening. And I don't know if you heard. But, I mean, I guess you did. But you are one of the good guys. Like I do genuinely see you as like a quality guy, like a man of. value and I just froze and

that's just the truth. I thought for sure you were checking for cameras under the bed but instead it was this. He brought for cameras for her. It was like just to make sure she's okay. I mean what a beautiful connection you two have and yeah I mean I'm open for it.

Open is good. Okay. We would have to get you back in the same city again in order for that to work out. I mean I'd be open to flying myself out. Ooh, now that's a commitment. I mean, Kyle, you've heard that she's open to it.

Where are you? Oh, yeah. I'm open. Like, that's everything she told me, like, after the relief of just knowing that I wasn't humiliating myself, knowing this, like, yeah, she seems like the person I thought she was, and I'd be very open to seeing her again. Oh, you mean seeing her the first time. Yeah.

Well, thank you for being understanding. Well, we'd like to help that first meetup happen just a little bit. offer to pay for your first date, wherever that may be. Oh. Or the flight bar? They do a good breakfast. Oh, the same hotel. We stayed at the hotel and ate the breakfast after she knew that you got ditched.

Of course, yeah. There was an omelette bar. Yeah. He was in the adjoining room, by the way. Can you imagine the sad guy crying next to the waffle station? We're not going to let that happen, Kyle. I promise. I'm going to be around.

All right. So it sounds like you're both in on this. We're going to pay for your next date, you two. Congratulations. Oh, thank you. Oh, my God. Please update us. I'm invested now.

Yes. I will. These usually go so terribly. I don't know how to end the good ones. Yeah. So talk to you later. Yeah. Enjoy your happy life together.

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shockingly, maybe for the first time ever on this show, the romantic gesture actually worked and didn't completely repel the woman? It worked too well. That was the problem. Exactly. Jose is exactly right. This is so

darling. Yeah, it's really sweet. It's like someone who's like great and wakes you up and it's like, oh my gosh, this is the real deal. And then you're like, I want this. I'm scared. Yeah, I'm scared. Like, this is a real love. On the same page, the cynic in me says, well, what was he supposed to say? He can't hear all that and been like,

I don't want to go out with you now. Give me a refund loser. In the end, it was a pretty sweet story. But just think about- We better get an update for them. We'll definitely be reaching out. But think of how powerful that would be in a normal relationship.

Like, Brooke, if you gave Michael a note for the 34 times you made him cry in the last week. So funny, Jeff. Have you been holding that joke for a long time? Remember when you didn't load the dishwasher You're right, Michael, and he has that note on his nightstand. Powerful stuff.

Remember you said, I love you and I didn't like your tone? Yeah. So I think we can apply Kyle's strategy to all different areas of our lives. In fact, you could give us a note with 34 reasons why you want our help, calling the person who isn't calling you back. You do not want that email. We're good for a couple reasons. No. 34, no one's going to read that email.

Just send one succinct email. Absolutely. We are not immune to your flattery. Our producer hates you right now. comment 34 flattering things on our podcast right now. You can find it at Broke and Jeffrey. Lisa, tell them about our new show. We have a new podcast.

It's called Don't Lie to Me. I'm Lexi Youanu. We're two best friends, 22 years apart, but so close at heart. And I'm Lisa Di Giulio, the old one, which means we have wildly different references, occasionally different opinions. And at this point in my 50s, I've lived it all. Now in my 30s, being the founder of new shoes, good taste, is my business. Listen on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

I'm Lacey Mosley, author, actor, stand-up comedian, creator, and host of Scam Goddess Podcasts. The True Crime Comedy Podcasts all about robbery, fraud, and those who practice it. Each week, I bring on an amazing guest. Ooh, I scammed them. What? I can talk to you for an hour. You're a generational yapper like me. That's why I had to make yapping a job. And now you can catch full episodes of my show on YouTube. Start listening to you. a scam goddess on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. I'm Hamza. And I'm Martin.

And we're the hosts of Out of Character. The best podcast in the world is that they said. Wait, they said that? Yeah, yeah, they said that. The best podcast with two best friends who jabber and talk about topical, trendy, funny stuff, give our input on it. That's what you've needed, I think, up until now, listener. Listen out of character on the IHeart Radio app, Apple Podcasts, or wherever you get your

podcast. Sometimes I just feel like a burden. bird. You fly. You're a martin. And we are out of character. Our podcast. Dude, you messed up the clip. There are thousands of podcasts that can tell you how to better yourself.

Get Worse with Kyle Pruh is not one of those podcasts. So if you're interested in getting thinner, going to therapy, starting peptide, setting boundaries, taking supplements, making your better, getting closure, then I would humbly recommend other podcasts. If you're interested in blackmail, love bomb, and cloning yourself

or getting revenge, then we've got a little something something for a dastardly individual. individual like you. Listen to Get Worse with Kyle Pruh on the Iheart Radio app, Apple Podcasts, or wherever you get your podcasts. If anyone wanted to commit a murder, up here would be the greatest place in the world to hide the body. But no one will find it. He acted friendly. He talked friendly. He sounded friendly. They all knew that I did the scary boogie stuff, and I said, maybe she'll find out where this girl is. I saw him violent. Backhanded her a pound. Listen to the Devil's Quarry Season 2 in the Bone Valley Feed

on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.