Episode · Brooke and Jeffrey: Second Date Update
Second Date Update: Third Wheel Steal
28 Sep 2026 · 19 min
Episode · Brooke and Jeffrey: Second Date Update
28 Sep 2026 · 19 min
The guy on the phone for today’s Second Date Update isn’t getting a call back, and it’s probably because the woman he’s interested in was on a DATE with ANOTHER MAN! He swears he can explain in the podcast! See omnystudio.com/listener for privacy information.
Speaker 1:All right, before we get to our new episode, thank you so much for finding the Brooke and Jeffrey official second date podcast.
Speaker 2:We appreciate that you're here. We got to revisit our.
Speaker 1:Raccoon boy Friday. I mean, it's still how I picture him. He's, I'm hoping, has left her apartment by now.
Speaker 2:I hope, but I doubt it. Yeah.
Speaker 3:You know, at the same time. And the comments were funny. We got one person who said, this is epic, priceless. To us, we called this person a leech, a free-living lifestyle.
Speaker 2:Why did this episode make me mad?
Speaker 3:Oh, a woman asked me to stay over for a few nights after our first date while my place was being fixed. We celebrated our 10th wedding anniversary next year, and we have a three-year-old.
Speaker 2:Life be lifin'. Maybe it'll work out for them. Maybe that's the update we'll get. Oh, God. I love when you guys put in your little stories in our comments.
Speaker 1:About how you met or how you relate or whatever it may be.
Speaker 2:Do that again today. Please. Your brand new episode starts right now. Brooke and Jeffrey in the morning. Second date update.
Speaker 4:We got an email this morning from a guy named Nick who went on a date with a woman.
Speaker 5:Kind of. I say kind of because, yes, he was on it.
Speaker 2:Yeah.
Speaker 5:But it wasn't his.
Speaker 2:What do you mean?
Speaker 4:I don't even want to try to explain it because Nick's email did kind of trail off and didn't have any periods or punctuations in it.
Speaker 1:I love to grammar shame people right at the beginning.
Speaker 4:It was a little hard to understand. So it might be a lot easier just have him explain it himself. So first of all, Nick, hey, man, welcome to the show.
Speaker 6:Hey, guys. Thanks for having me.
Speaker 2:Is that an exclamation park at the end of your sentence?
Speaker 5:An exclamation park?
Speaker 7:Wow.
Speaker 2:I said mark. I meant to. I don't know if my mouth didn't work.
Speaker 7:What?
Speaker 2:Nothing.
Speaker 6:Exactly.
Speaker 5:Never mind. Why don't you just tell us what happened?
Speaker 4:How were you on a date that you weren't really on?
Speaker 6:Oh, yeah, dude.
Speaker 8:I mean, like, my brother is, like, this genius tech guy, right?
Speaker 6:Like, all IT and all that, right? He's super smart.
Speaker 2:I like how you say right as if we know him.
Speaker 5:Yeah. You're totally right.
Speaker 2:Yeah, I love your brother, man.
Speaker 6:I mean.
Speaker 5:Your brother's cool.
Speaker 6:Yeah, he picked me up from the bus station. We were going to Uber back to his place and drop off our stuff. But then he gets, like, this text from this random girl that he forgot he had a date with. Yeah, so we were like, screw it. Let's just go to this place and get rid of this girl, and then we'll go home.
Speaker 2:Get rid of this girl?
Speaker 4:Okay, well, so your brother had scheduled a date with a woman, forgot about it, and you were with him at the time, so you just decided to tag along?
Speaker 6:Yeah.
Speaker 2:Okay. I'm hoping you're meeting somewhere casual.
Speaker 6:Yeah. I mean, yeah, it was just bar, you know? Okay.
Speaker 5:What is this woman's name? Stephanie.
Speaker 6:Stephanie.
Speaker 1:Stephanie, okay Talk me through You show up at the bar You're with your brother Stephanie's already there, I'm guessing What happened?
Speaker 6:Yeah, she was like Wearing this after work outfit suit thing And I'm like in sweatpants And like still smelling like the bus So that was already kind.
Speaker 4:Of awkward What was her reaction to seeing you Tagging along with your brother?
Speaker 6:Yeah, I mean she was surprised But my brother explained that I'm his brother And I was in town for the weekend So It was all good. She was fine. Yeah.
Speaker 5:Hold on, though.
Speaker 1:This is like a date that you're, like, they're interested in each other. He can't move in on this woman. Like, is your brother not interested in her at all?
Speaker 6:Well, I mean, something you don't know about my brother is, like, he's this, like, really good-looking guy. So he has, like, a bunch of options. So it's really not a big deal.
Speaker 1:Oh.
Speaker 2:So did you ask him for her?
Speaker 5:Like, you were interested in her?
Speaker 6:I'm confused.
Speaker 2:You're asking too many questions.
Speaker 6:Yeah. Well, just sitting at the bar chit-chatting and stuff. And then my brother kept getting, like, hit up by, like, different women on his phone. And, like, that was, yeah. Like I said, man, he's a stud.
Speaker 5:You guys are important players.
Speaker 2:It feels like you're quite the package together.
Speaker 1:I imagine she's a little overwhelmed. The guy she's supposed to be going out with is on his phone talking to other women.
Speaker 2:And you're in dirty sweatpants, smell like the bus.
Speaker 5:In the best kind of way, she means that.
Speaker 6:Yeah, you know, I get it. No offense taken.
Speaker 5:Okay.
Speaker 6:Yeah. So anyway, so that was like my chance to like talk to her and stuff, you know, we kind of had a thing going because like he wasn't paying attention. All right.
Speaker 4:So, I mean, you're basically painting the picture for us that your brother is basically completely ignoring this woman.
Speaker 7:Yes.
Speaker 4:So you're stepping in like a hero and talking to her, which is very kind of you. Do you get the sense that she's, do you get the sense that she's feeling interest in you?
Speaker 6:I mean, I was definitely interested in her. I don't know if she was interested in me, but she was talking to me, so that's really all I cared about in the moment. Okay.
Speaker 5:All right, getting responses.
Speaker 2:What are some of the subjects you guys covered?
Speaker 6:I mean, we talked about, like, you know MLB the show, the video game?
Speaker 2:Yeah, yeah.
Speaker 5:Oh, yeah, the baseball game.
Speaker 2:My son loves that game right now.
Speaker 6:Yeah. Yo, I love that game. I play that game every day, man. I'm the starter shortstop for the Cubs, man. Like, I'm winning MVP. You already got.
Speaker 5:Drafted, huh?
Speaker 6:Why? Oh, I got drafted. I got drafted by the Rockies, and then I was like, no, I don't like this team. Trade me. And so they traded me to Cleveland, and then I was just doing nothing for six years.
Speaker 5:Yeah, so I'm assuming that she left then.
Speaker 6:Yeah.
Speaker 1:Um, what?
Speaker 6:I don't know.
Speaker 5:She stayed and listened? Like, she was into it?
Speaker 8:Yeah.
Speaker 6:My brother actually left. Like, after 40 minutes, after 40 minutes, he was like, he pulled, like, a move. And, like, he was like, I got to go. I got to take my brother back to my place. And, like, so I was like, dude, why would leave me?
Speaker 5:Like, she totally lost me.
Speaker 2:Oh, my God.
Speaker 6:And so we left. And so, like, he was, like, showing me all the hot chicks on his phone and stuff, like, hitting them up. I was like, that's great, but, like, you took me away from, like, my hot chick. And, like, he was like, if you want Stephanie, she's yours. Oh, God. And he gave me her number, so I've been texting her a couple times.
Speaker 1:I feel like I'm getting punched in the face right now with information.
Speaker 8:What?
Speaker 5:It's so much coming at me.
Speaker 2:I'm so happy it's just one brother on the phone.
Speaker 4:Brooke's saying it sounds like the love story of the ages, and we want to help you.
Speaker 6:Stop.
Speaker 5:Get together with Stephanie.
Speaker 6:Oh, yeah, man. I'm just a hopeless romantic over here, man.
Speaker 4:Yeah.
Speaker 5:That sounds like it.
Speaker 6:Definitely.
Speaker 2:Did you reach out to Stephanie at all?
Speaker 6:Yeah, I've been texting her stuff. And, like, I was like, hey, it's the guy from the bus in the sweatpants.
Speaker 5:And she gave us mine.
Speaker 2:Oh, what?
Speaker 4:How?
Speaker 8:I know.
Speaker 1:Can I ask, in the 40 minutes that you told her about the show, did you ask her any questions?
Speaker 4:Yes.
Speaker 2:That's a lot of silence.
Speaker 6:I know she likes whiskey. And I got to tell you, man, she is not a lightweight. Okay.
Speaker 2:It's funny.
Speaker 4:And the whole time that we've been talking to you, that was the one moment of silence that we got for like two seconds.
Speaker 2:I mean, maybe next time that would be a good way to have a conversation.
Speaker 5:What?
Speaker 6:Talk about the whiskey?
Speaker 7:Yeah.
Speaker 5:So Brooke is saying she thinks there's going to be a next time.
Speaker 6:You think so? Yeah.
Speaker 5:After we get her on the phone here. Oh, don't, man.
Speaker 1:I mean, I think your good qualities are you have a lot of energy and you're really passionate.
Speaker 6:Oh, thanks.
Speaker 2:And there's some other things we could work on.
Speaker 6:Yeah.
Speaker 4:I like the optimism that we have going in the room right now. We're going to keep it rolling when we call Stephanie and ask her why isn't she calling back the brother of the guy that was at the bus stop at the bar.
Speaker 2:We'll come up with a better way to phrase that, Jack.
Speaker 5:Well, you've got to jog your memory somehow.
Speaker 4:The short stop for the Cubs.
Speaker 2:Yes, exactly.
Speaker 5:Okay?
Speaker 2:She could be dating an MLB player.
Speaker 4:Yeah, we're going to hook you two up and do your second date update right after this.
Speaker 6:Hold on.
Speaker 2:Brooke and Jeffrey in the morning. Second date update.
Speaker 4:You never know where you're going to find your soulmate. They could be waiting for you on the apps, at the gym. They might even be out on a date with your older brother right now.
Speaker 1:Your older, more attractive, more successful brother.
Speaker 4:Yeah. And that's what our listener Nick did. Third wheeled it when he came to town to visit his bro and suddenly found himself tagging along on a date. And kind of ended up falling for the woman that his bro was supposed to be bonding with. His brother was super busy, though, texting other cute girls the entire time and decided to give Nick the green light and Stephanie's phone number saying, hey, if you like her.
Speaker 5:Go for it.
Speaker 2:In this recap, I think that the brother is the one that ruined this for you.
Speaker 1:He sounds like such a jerk that I bet she couldn't even concentrate on how great you were.
Speaker 5:Yeah.
Speaker 6:That's all I'm saying.
Speaker 2:Yeah.
Speaker 5:Okay.
Speaker 4:Now we have a villain in this story. Your older brother is the one that kept you from your true love.
Speaker 3:Yeah, because he actually cares about this girl and liked her, right?
Speaker 5:The brother is like going through a list of other girls.
Speaker 6:Totally.
Speaker 1:Nick, are you okay with Jeffrey throwing around soulmate and love so much?
Speaker 8:You know what?
Speaker 6:I've thought about it, guys, and I think I actually do love her. What?
Speaker 5:Oh, no.
Speaker 2:That's a joke, right?
Speaker 7:Bro.
Speaker 6:Okay. I cannot wait to.
Speaker 5:See what I like that.
Speaker 6:Yeah.
Speaker 2:What's going on?
Speaker 5:Let's just call Stephanie.
Speaker 6:Please.
Speaker 4:The suspense is killing me. I'm going to dial her number and see if she picks up.
Speaker 2:Okay.
Speaker 4:Hello?
Speaker 5:Hey, is this Stephanie?
Speaker 6:Yes, is this?
Speaker 5:Hey, Stephanie.
Speaker 6:Hey.
Speaker 5:This is a radio show called Brooke and Jeffrey in the morning.
Speaker 1:Oh, man.
Speaker 2:Oh, yeah. Do we have a surprise for you?
Speaker 5:Good morning.
Speaker 8:Beyond that you're calling me right now?
Speaker 2:Yeah.
Speaker 5:I know this is probably a little odd, and we don't want to, like, interrupt your day, too.
Speaker 6:A little. Yeah.
Speaker 4:But this is a segment that's kind of odd by nature. It's called the Second Date Update.
Speaker 2:Okay. Never heard of it, Jeff.
Speaker 4:Okay, so what it is is if we have a listener that goes out on a date with somebody and afterwards that person isn't calling them back, they'll reach out to us to see if we can get a hold of that person that they like to see if there's a reason why.
Speaker 2:And I am so excited to hear your side of this date.
Speaker 4:Yeah, because the guy that emailed us, he wasn't the one that was supposed to be going on a date with you.
Speaker 5:It was the guy's brother, a guy named Nick.
Speaker 8:Okay, yes, yes. Nick.
Speaker 5:The shortstop for the Cubs.
Speaker 7:You're talking about Logan, right?
Speaker 8:You're talking about his brother Logan, right?
Speaker 2:No, Nick is the one that called us.
Speaker 4:Yeah, I don't know his brother's name, but maybe Logan's probably the guy you were supposed to go with and Nick is his little bro.
Speaker 8:Yeah, I just, I don't really understand why his brother would be Why is he talking to me through his brother?
Speaker 2:No, no, no, no. I think that's a miscommunication.
Speaker 6:There's a confusion.
Speaker 5:Yeah.
Speaker 4:So Nick felt like there may have been a connection building between the two of you.
Speaker 6:Are you serious? Yeah.
Speaker 1:So he's not, we're not calling for the brother. We're calling for Nick. Nick's the one that likes you.
Speaker 6:I don't even know what that means.
Speaker 8:I didn't agree. To go on a date with Nick, though, the date was with.
Speaker 7:Yeah.
Speaker 5:Right.
Speaker 4:Didn't it kind of feel like it was turning into a date?
Speaker 2:Didn't you feel a little chemistry?
Speaker 8:I mean, if you're talking about the buzz from the cocktail I was drinking, then yeah, I think I was feeling some... chemical reactions well.
Speaker 1:He described his brother to us and the brother sounds like he was so rude to you like on the phone the whole time totally not interested i mean.
Speaker 7:His brother is a really busy guy he has a very hectic job and his brother was in town so honestly i thought that.
Speaker 6:I was talking to his.
Speaker 8:Brother really to help logan out to entertain him that he forgot that he was even coming to town. I figured he just had a lot going on and this was an unexpected thing that happened.
Speaker 7:But I mean, I see he's got a great job and he, and he's really good looking.
Speaker 6:Okay.
Speaker 4:So Logan told you that he had forgotten about his brother.
Speaker 5:Well, not that he had forgotten about the date.
Speaker 8:Yeah, of course. You're going out with me. You're not going to forget about me.
Speaker 6:Okay.
Speaker 2:This brother sounds like, I'm sorry. Yeah. Don't work.
Speaker 4:I feel like Nick is the one that had a little bit of a stronger connection with you, at least that day. And don't take it from me because we actually have Nick connected on the phone right now, listening in on this conversation.
Speaker 5:See? Oh, wow.
Speaker 2:Oh, he's just yelling.
Speaker 6:Oh, yeah.
Speaker 5:That's Nick, you remember.
Speaker 8:Nick, what are you doing?
Speaker 6:Right now I'm scratching my knee because it's like it won't stop itching.
Speaker 2:Oh, my God.
Speaker 4:Okay.
Speaker 7:No, I mean like with bringing me on the radio.
Speaker 6:Oh, that.
Speaker 8:Well, you wouldn't answer my text, so I figured I had to find out how to.
Speaker 6:Get a hold of you. Oh. Okay.
Speaker 8:You didn't maybe pick up on the fact that I did not want to get a hold of?
Speaker 6:Oof. Well, I figured you're busy, you know? It's busy season.
Speaker 2:I feel that. Yeah, I feel.
Speaker 5:Like we got that.
Speaker 8:One could say that.
Speaker 6:I just don't understand. Like, you don't want to see me again? You were so interested in, like, what I was talking about, so.
Speaker 8:Look, I had plans to be on a date that night. I was free. That was the time I allocated on my calendar to drink whiskey.
Speaker 6:And, you know, shoot the you-know-what. So... No.
Speaker 5:I mean, it was... It's like, explain.
Speaker 8:That wasn't the plan.
Speaker 6:It was just a blip. It was a blip in the universe. A blimp?
Speaker 5:No, a blip.
Speaker 6:I don't understand.
Speaker 4:He's just trying to focus, I think. Something you don't know is that Nick had a lot of really nice things to say about you specifically during your time hanging out together.
Speaker 5:He felt a spark.
Speaker 7:You're probably just trying to get to me for Logan, right?
Speaker 8:Because Logan thinks that.
Speaker 6:No no logan logan's already like dating like three other girls right now yeah.
Speaker 8:Okay he's hot and he's loaded.
Speaker 4:I know listen look i know he's really good looking i'm not gonna lie but i'm not ugly.
Speaker 6:That means we have the same genes like genetics not like you.
Speaker 5:Know Not pants.
Speaker 1:I mean, tell her. Tell her you weren't at your high point. You just got off a bus and you're in sweatpants. If you're somewhat attracted to him in that state, then you'll probably clean.
Speaker 2:Up real well.
Speaker 8:I never said that I was attracted to him. I never once said that.
Speaker 6:Okay.
Speaker 2:Well, that's true.
Speaker 6:But you didn't say you weren't. Okay.
Speaker 5:He's got you there.
Speaker 8:What are we even doing right now?
Speaker 7:I don't know anymore.
Speaker 6:I'm just trying to get your love, Stephanie.
Speaker 4:We're watching the fireworks explode right in front of our very ears.
Speaker 6:My love?
Speaker 5:You worded that wrong.
Speaker 7:No, this is how this is how.
Speaker 8:This is how docu-series about serial killers start.
Speaker 4:No, I would never.
Speaker 2:This guy's kind of funny, Stephanie. He's just genuine. If anything, I'd do it for the plot.
Speaker 8:This is an excellent inciting incident.
Speaker 6:Is this a money thing?
Speaker 5:Look, Logan makes a lot of money.
Speaker 6:I get it.
Speaker 1:He does.
Speaker 6:You know about Kalshi? I'm going to make these bets. I got the Jets making the Super Bowl.
Speaker 5:I got the Jets making the Super Bowl. The sports betting. Sports betting on there. Polymarket.
Speaker 1:Betting was stupid that's a really good idea for your financial future.
Speaker 6:So like are we good are we doing this.
Speaker 4:Or what this is the right time to ask has he not been listening just ask her Nick wants me to ask you Stephanie if you'd be interested in going on an official date with Nick Not his brother.
Speaker 5:Absolutely not.
Speaker 7:Well, hold on.
Speaker 1:And listen, Stephanie, it's not going to ruin your chances with his brother.
Speaker 2:I promise you the brother is not going to call you.
Speaker 5:Plus, we'll pay for the date.
Speaker 6:Yeah, he's got like a billion other options with women. But, like, I don't.
Speaker 8:Oh, God.
Speaker 5:Don't say that. I don't want them to know that. That's quite a selling point. Look, I'm desperate.
Speaker 2:Who doesn't want to drink whiskey with this guy, Stephanie?
Speaker 6:Come on.
Speaker 5:It'll always be a fun night regardless. It's a huge ego boost.
Speaker 8:Are you guys genuinely trying to get me to go on a date with this guy? Like, is this what you want from me?
Speaker 5:Well, yeah, we were.
Speaker 4:I mean, one thing that I forgot could be a hiccup is that, Nick, you live in a different city.
Speaker 5:Then Stephanie does. I'm not sure how that would work.
Speaker 6:It's funny that you mentioned that. Because, like, me and Logan are actually in a fight right now. So, Jeff, could I at least, like, stay at your place for a few days?
Speaker 2:Oh, because you're in town still.
Speaker 6:Oh, I see.
Speaker 5:Absolutely not. So, okay. It seems like I'm picking up it might be a no.
Speaker 6:You think so?
Speaker 5:Jeff, you're just as bad as him. Yeah, I'm sorry, Nick. I think Stephanie is still interested in your brother.
Speaker 4:Yeah.
Speaker 6:That's really disappointing.
Speaker 2:Is that true, by the way?
Speaker 4:Even though you know he has all these girls, are you still interested in the brother?
Speaker 8:I love competition.
Speaker 2:Oh, God.
Speaker 5:Oh, my God.
Speaker 6:Stephanie, you like competition? That's good, because, like, I have this link for Kelsey for, like, $ 5 off. Oh, God.
Speaker 2:Oh, my God.
Speaker 6:Oh, God. I'm just saying.
Speaker 8:All right.
Speaker 2:Well, yeah, we heard what you were saying.
Speaker 5:It didn't work this time, Nick.
Speaker 4:You're not going to be going out with Stephanie, but good luck winning the pennant with the Cubs this year.
Speaker 5:I think this is your year.
Speaker 6:Oh, thanks. We're making a push, guys.
Speaker 4:Brooke and Jeffrey in the morning. You guys, I know we just talked about Logan, but there's a reason why we don't get callers like.
Speaker 5:That on this show.
Speaker 2:Wait, like the successful brother?
Speaker 5:The successful brother?
Speaker 6:Yeah.
Speaker 4:Because they're swimming in it. Women are swarming him. They don't need us, but we need them.
Speaker 2:Do we?
Speaker 5:I don't want to talk to him.
Speaker 2:I don't like him either. I don't even know the guy and he sounds like a jerk.
Speaker 5:Exactly. And that's entertaining.
Speaker 4:We need to put out an APB for all the hotties who got rejected for the very first time in their life. Because I never have personally, so I wouldn't understand what they're going through. But Brooke's been rejected many times.
Speaker 2:I don't know.
Speaker 1:I seem to remember a story of you crying in some frat house a couple of times during college.
Speaker 5:Okay, yeah, I've been through some adversity. Sure. I'll admit that. But rejected outright? That's more of a Brooke thing.
Speaker 4:By many men, ugly and hot. homeless and homed. So will we be compassionate? Some of us will.
Speaker 5:I'm also a loser. I just wanted to join in on this.
Speaker 2:You're in the Brooke boat.
Speaker 5:Let me in, Brooke.
Speaker 2:Why are you coming at me?
Speaker 5:Come be in Brooke's boat.
Speaker 4:We'll all be in it together and call that person who's not calling you back. Let's weep collective tears with a second date update and go check them out online wherever you get yours at Brooke and Jeffrey.
Transcript supplied by the publisher with the episode.
by iHeartPodcasts · English · Comedy
Ghosted after a first date? We call the person who isn't calling you back to find out the real reason why and get you a Second Date. Low success rate...high entertainment for the rest of us. Want more? Catch the FULL hour long show over at Brooke and Jeffrey: iHeartRadio : https://www.iheart
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