Brooke and Jeffrey: Second Date Update - Second Date Update: Three Wheelin' It

Episode Date: May 28, 2025

One of our listeners is confused after his date ended in the WEIRDEST way ever… but he still has SOME interest, so it couldn’t be that bad. Hear the brand new Second Date Update in the podcast! Get your 2nd Date Update Merch For A Cause HERE! See omnystudio.com/listener for privacy information.

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covering the Diddy Trial on the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. The Made for This Mountain podcast exists to empower listeners to rise above their inner struggles and face the mountain in front of them. So during Mental Health Awareness Month, tune into the podcast, focus on your emotional wellbeing, and then climb that mountain.

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Police Lieutenant Joel Kern used his badge to fool everyone. Most of all, his wife, Caroline. He texted, I've ruined our lives. You're going to want to divorce me. How far would he go to cover up what he'd done? The fact that you lied is absolutely horrific. And quite frankly, I question how many other women are out there that may bring forward

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May is Mental Health Awareness Month, and Deeply Well is a sanctuary for your healing. I'm Debbie Brown, healer, well-being expert, teacher, and fellow seeker. And each week we explore what it means to become whole through soul expanding conversations and practices. Today, wow, I feel really powerful and ready to serve and use my skills. And it's like, that's the heart of what it is to be an authentic woman. To hear this and more ways to prioritize your peace, listen to Deeply Well from the Black Effect Podcast Network on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

AT&T, connecting changes everything. All right, brand new second day podcast for you today. And it is Brooke and Jeffrey in the morning. It is bonkers to me. Okay, you show up to a date Mm-hmm. There's another person there besides the person you're going on the date with. Oh, do you stay or do you go? I ask questions Well, it depends if it's another guy maybe I stay and see who's hotter but if it's a girl This is a wild one. I can't wait to read the comments after this

to see where people stand on this issue. But let us know right now, Alexis, what are you seeing in the comments? Speaking of comments, I feel like they've been extra good lately. Yes. They're always good, but you guys are just really leaving some funny ones for us.

People are putting effort in. Yes. And Rebecca Miller said, my son and I love listening to y'all. He's six. And every time we get in the car, he has to listen to Booger and Jeffrey. I'm officially changing my name. That's it, I'm Booger and Jeffrey.

That is so good. All right, here's your second date. Remember, enjoy and hit that like and subscribe. Thanks so much for being here. Second date update. We've been doing these calls for a while now and found it's not unusual for a woman to bring one of her friends along with her on a first date. Yeah, I mean it's normally, yeah, normally you tell someone beforehand.

Depending where she sits at the place too. Sometimes they're upfront about it and just very open. Sometimes though they keep it a secret where they have them hide somewhere in a nearby booth or inside of a decorative plant Spying with binoculars to make sure everything's kosher. I'm sure you won't get noticed then yeah, so yeah We've definitely heard that before but is it unusual if the friend that she brings with her is a guy? Oh man, yes. Because apparently that happened to one of our listeners recently. Leo, is that true your date showed up with another dude?

Uh, yeah. Oh wait, that can't, I mean I have guy best friends. Yeah, me too. You know, that could be fine. Did she tell you beforehand that that was what was gonna happen? No no By the way Brooke has hooked up with almost all of her guy best friends So I don't know if it's a great thing because you gotta just try it out and see if that's how you like each other And then you're like that didn't work looks like you're bringing her friend. Yeah Run us through how this all happened.

Like start with how you met her. So like I met this girl, Christy. I mean, it's this bike club. It's like a group on Facebook and people get together. We like ride every like couple of weekends. And that's cool. I started talking to her. Yeah, no, it's actually awesome. And I've met a lot of people, but I met Christy and I just really liked her.

And I asked her out What a great way to ask somebody out like you already have shared interest. Yeah, no, and she's amazing I know I was so excited. Okay, and I show up and she's there but she's sitting at the table with this other guy And she's like, oh, yeah, this is David No, if they go title for David or distinction like not my brother or my friend or my parole officer Yeah, how was the vibe like between them did you feel like they had chemistry did it feel friendly did it feel sexual good question I mean, they were definitely really comfortable with each other. Okay This is my first thought is either she is in a open relationship and thought you

maybe knew. Could that be it? Well, did not get a heads up by any means on that. Okay. Okay. And like, don't get me wrong, like David's a nice guy, but like there would be moments where they would just talk with each other or make obviously like inside jokes that I Paid for the dinner And for David it seemed like he was just part of the package and I'm still not sure how to unpack that I could see why naturally you're like I'm on a date I offered to pay so I'll pay for whoever of a guy friend though to be okay. Why would a guy friend want to sit

in on you on a date? That's why I feel like you really could be besties like my best guy friends would tell me that's weird. I get it that like women want to make sure that there's someone around them like I can understand that but I was just so shocked that it was this guy. Well yeah and typically it's like you want security if it's somebody you've never met before You've already met this person you meet up with them once a month that during a bite down like You should have some rapport. I think I gave a pretty good impression that I'm not a serial killer, but I respect that boundary So wait, did you ever find out who he was? No. How did the date end?

No okay so we were there for like an hour and a half we did flirt like we all had like collective conversation. Oh so you were flirting with David too. Not just because of him. Good man make her jealous. I mean I wasn't going to be rude but it was so weird that when I left I sort of just almost jokingly like reached out and gave them both a group hug. Wait, you group, wait, together? Well, they were going to leave together. So I just hugged them both. That's a good one. Wow. I actually like that.

I was like, we should all hang out again sometime. And I don't know why the hell I said that. You handled it so well. Yeah, cause if that is her bestie then he'll be like oh, he was a nice guy He hugged us bad or you just friend-zoned yourself Yeah, maybe that's the risk you take when you're on a triple date. You weren't planning on that's true So where are we at now with you and Christy? Oh? Yeah, all right, so the way I handled that gets me into this situation where I'm the one that's not responding and she has been calling me and texting me and

they want to know when we should all hang out together. And I don't know why I said it, but now I'm like, I really don't want to hang out with David. Yeah, obviously. You gave him a hug like you basically let him on. I feel like she's setting you up with him right now. What do you want us to do? My goal is to have a one-on-one date with her. That's what I wanted originally and I don't know if that's even possible anymore. So you want with our call here for us to surgically remove David from the situation and have it just Be a one-on-one with you and Christy. Let him out of it Okay in the most respectful way possible. We need to figure out how to convince her to do that No, it's cool dude, but he doesn't I don't want to hang out I don't want to date David

But he's really handsome though, right? No comment. Oh my god. The more handsome he is, the harder this is going to be. We're going to find out when we call Christy and try and get you your second date update coming up right after this. Hold on. Second date update. In the dating world, it can be hard to get just one person wanting to hang out with you But our listener Leo is a lucky man

Interest from two people same time Situation one is his date Christy the other is the random dude that Christy came to the restaurant with that night named Yeah Yeah, we can't even say friend because I guess we didn't get closure That's the thing we don't know is David her friend her brother her lover her stepdad We don't really know that was never made clear the entire night, but David got a free meal It's possible. The thing is, it's awkward because Christie's been asking if all three of them can hang out together again.

But Leo isn't really up for that. He wants to cut David out of the picture. Yeah, look at that, David. So that's why he's asked us for help today. You're not David. No. You're Leo. Sorry.

Too late, man. He's just excited for all the guys. This is why I can't juggle more than one at a time. She wants to flirt with both of ya. Yeah. Yeah. You don't seem as excited as we are. You didn't even consider the stepdad option, did you?

I think it's so wild, you went through an entire dinner and you still couldn't figure out how David was connected to your friend, Chris, your date, Christy. I know, like, it was awkward and I just didn't know how to play that so who are you I kind of get it you're just going with the flow void conflict yeah yeah I can't wait to hear how David feels about the group hug that's right they did have the three-way hug yeah so they're at least connected by our boy Leo. Yeah out of panic it sounded like I didn't know what to do. I did panic a little I it was weird

Yeah, so I think you handled it Okay, wait for this call, but we're gonna try and help you out just to get a date with only Christie if she's even up for that I don't know Is only David an option? No, I don't think he's into that. No offense, but no. No offense taken, everybody has their own likes. Yeah, but Christy might take offense.

So let's call her and see how she feels about it. Hopefully she picks up, here we go. Hello? Hey, is this Christy? Yeah. Oh. Hey, Christy. Hey. How are you doing today?

Good morning. You're on a radio show right now called Brooke and Jeffrey in the Morning. Okay. Yeah. Sorry, I'm confused. I know. It's okay. We're doing a segment right now called The Second Date Update.

We're calling on behalf of now called The Second Date Update. We're calling on behalf of one of our listeners and friends of the show that you went out with recently named Leo. Yeah, Leo. I mean, I've been texting Leo. Right. We heard a little bit about your hangout and I don't know the right way to say this. This is different than we

normally do. It is different. We know that you're interested in seeing him again. He said that there's been communication about setting up another hangout between you, Leo, and the other guy that was there that night named David. It was a fun night. I mean it sounds like it there's a little bit of a question mark though around You know basically what's going on? Well, we're trying to figure out what the dynamic is between the three of you Right Okay, well, I'll explain it but first like you think there's any way you can like help me convince

Leo to go out with me again. I mean I really liked him and I kind of thought he liked me too like Yes, with you. I don't think we'll have any problem getting him to agree to go out with you Honestly, I think it's like sold the problem that Leo has is with the David part No, no, you have to go out with me and David. What? What are you guys like a package or something? Why is it so important that it has to be all three of you going out at once? Actually, it's more than three of us. There's a fourth. What? Hold on.

Wait, wait, there's more. This is a love square now. The guys aren't connected. Wait, wait, is it another guy This is a love square now The guys aren't connected. Wait, wait Another guy or is it a girl? Okay, so it is another guy but it's not what you think You got to clear this up for us Christie we're really can Know know what really isn't okay. So the third guy the fourth person he was actually filming secretly he was filming our date

In the restaurant to he was just another table kind of pretending he wasn't doing what he was doing Why because I am really doing well on tick tock right now and there's this trend It's called two dates one night. Two dates one night? Two dates one night. Oh, uh oh. Like a challenge? Yeah, two date one night challenge. So wait, so you set up a date with David and set up a date with Leo at the same time all

for TikTok? Yeah, and it's doing really really well. My video, it's like it's totally going viral. But it's all for clouds! So is it authentic? You didn't like these guys? going viral why didn't you tell him because then it wouldn't be a good thing everyone would know what stage so part of the challenge is going on a date with two guys at the same time and neither of

them knows about it yeah but I'm interested in both I like both so wait that means in the comment section they must be voting for who they like the most Oh my god I kind of live in this now Exactly there's so many people voting Oh my god Are you some like wizard that you're able to get these two guys to stay? That's insane Brooke be careful your jealousy is showing No I think that's crazy

You must be like so lovely and like such a personable charismatic person In order to convince two dudes to hang around What about that, but I'm not that looking Leo's having as much fun though Listening and hearing all of this because Christy you should know leo is on the phone right now You should know Leo is on the phone right now This for our podcast ruined my Leo man, are you still there? I'm just trying to process what I just heard

I didn't know what to expect. It was weird to begin with, but this was like, I'm honestly weirdly impressed in a way. But I feel like I went through the same emotions. And Brooke said that. Yeah, she's impressed too. So this is all a social media thing? Yes, but I do like you. She likes that you get her lots of views. That's for sure.

It's her social experiment. I mean, what were you going to do at the second date with Leo and David again? Yes, but I do like you. She likes that you get her lots of views. That's for sure. It's like a social experiment. I mean, what were you gonna do at the second date with Leo and David again? That's the best thing is to have a part two of your video. No, but like, was that gonna be the big reveal? Was that when you were gonna tell them? No, I was gonna do a sequel first, obviously.

Yeah. She was gonna reveal at the double marriage when they're both on the altar at the same time by the way guys This is all on TikTok. They still don't know who each other are Who will show up at the wedding? We'll see when the doors open Yeah, if I'm Leo, I would question whether or not your feelings were valid Yeah, that's fair, but we did go on a date. It was a good time and I do like him Oh my god

Yeah But we did go on a date. It was a good time and I do like him Oh my god Yeah, but if the tables were turned and you showed up to a dude and he had another girl sitting there that's different I mean it's different when you're a girl She's hot remember Every other rule in the book so Leo you've been listening here. You've kind of heard what Christy has to say Do you believe her? I don't think it's that I don't believe you. I don't understand What this is or why you would do it But you were Leo all of social media is hard to understand why things are the way that they are and why things get popular It doesn't make any sense. This feels like explaining any tick-tock trend to Jeff

It doesn't make any sense. This feels like explaining any tick-tock trend to Jeff So we would like to arrange that second meetup if you're still open to it Leo Wait, why are we asking him? Well things have changed cuz now that Leo knows more about the whole situation And the motives I think it's only fair since he's our listener to get the okay from him first. Oh for sure. I just can't believe you want to. Well let's find out. So Leo I'm just gonna go ahead and ask you would you be willing to go out again with Christie or Christie and David or maybe just David? Come on there's options Jeff. I mean there's a lot of different ways you can work a triangle. Yeah. Hammer Guy? Don't forget about him work in yeah Interest on the other side that's not gonna work. I not for me. No, okay Okay, well, I mean I'm a little disappointed and I don't want this to sound weird kind of awkward

But do you know anyone that looks like you? It's really doing well. You can't trick the Leo fans. You're crazy. Oh. Who does that? I'm crazy? Yeah, I'll be crazy famous pretty soon.

So you missed out. Oh, man. I think famous and infamous are two different things. Still, Leo, you're going to look back at this call as the moment that both of your ones got away. Oh. That doesn't add to it too, right? I don't know how it works either. David does owe me dinner though.

Yeah, he does. I would watch that TikTok video for sure. Brooke and Jeffrey in the morning. Well, that was unexpected. Wow. Yeah. Honestly, like, I feel like there's so many other options that would have been better. Yeah. Better answers. Couldn't have predicted the two dates, one night, TikTok challenge was the reason.

And where's David? Where's David's outrage at this? Is he just going along with it all? Does he know? I think maybe he appreciates all the fame that he's getting from TikTok. No, I feel like he doesn't know. I think he's out there wondering who the hell Leo is. Maybe. That's possible. Also, I'm kind of offended that none of us have been involved in a two dates one night tick-tock challenge

Where is our invites to be in one literally don't date you can DM? Oh, yeah, I should go check out the for you page But look I understand Leo's stance It's just sometimes I think you need to put your standards and your self-respect to the side In the name of social media infamy, it's a small price to pay Yeah, it says the guy who barely posts a picture of his dog exactly I could be famous, but I don't feel like it right now That's where I'll be famous, but I don't feel like it right now. No, that's what it is. That's where I stand.

That's good. I'll be there one day though. Okay. And you could be in a nice thruple or maybe in just like a one-on-one relationship if that's what you want. Yeah, whatever you want. Exactly. Email the show.

We'll call that person who's not calling you back and go check out all of our second day podcasts wherever you get yours at Brooke and Jeffrey. Amy Robach and TJ Holmes here. Diddy's former protege, television personality, Danity King alum Aubrey O'Day joins us to provide a unique perspective on the trial that has captivated the attention of the nation. It wasn't all bad, but I don't know that any of the good was

real. I went through things there. Listen to Amy and TJ Presents, Aubrey O'Day, covering the Diddy Trial on the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. The Made for This Mountain podcast exists to empower listeners to rise above their inner struggles and face the mountain in front of them. So during Mental Health Awareness Month, tune into the podcast, focus on your emotional well-being, and then climb that mountain. You will never be able to change or grow through the thing that you refuse to identify,

the thing that you refuse to say, hey, this is my mountain, this is the struggle. Listen to Made for This Mountain on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I'm Andrea Gunning, host of the podcast, Betrayal. Police Lieutenant Joel Kern used his badge to fool everyone. Most of all, his wife, Caroline. He texted, I've ruined our lives. You're going to want to divorce me.

How far would he go to cover up what he'd done? The fact that you lied is absolutely horrific. And quite frankly, I question how many other women are out there that may bring forward allegations in the future. Listen to Betrayal on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. What happens when we come face to face with death? My truck was blown up by a 20-pound anti-tank mine. My parachute did not deploy. I was kidnapped by a drug cartel.

When we step beyond the edge of what we know... I clinically died. The heart stopped beating. Which I was dead for 11.5 minutes. ...in return... It's a miracle I was brought back. ...Alive Again, a podcast about the strength of the human spirit. Listen to Alive Again on the iHeart Radio app, Apple podcasts,

or wherever you listen to your favorite shows. Being able to say, I feel like crying, so I will cry. Today, I'm a little depressed. May is Mental Health Awareness Month and Deeply Well is a sanctuary for your healing. I'm Debbie Brown, healer, wellbeing expert, teacher, and fellow seeker. And each week we explore what it means to become whole through sole expanding conversations and practices. Today, wow, I feel really powerful and ready to serve and use my skills. And it's like, that's the heart of what it is to be an authentic woman.

To hear this and more ways to prioritize your piece, listen to Deeply Well from the Black Effect podcast network on the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. AT&T, connecting changes everything. You're listening to an iHeart Podcast.