Brooke and Jeffrey: Second Date Update - Second Date Update: Red Flag Test

Episode Date: November 3, 2025

We needed the listener on the phone today to be 100% HONEST about what happened with his date, and that proved to be harder than we realized…See omnystudio.com/listener for privacy information.

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We're so glad you were here. It's Brooke and Jeffrey, and this is your second date update podcast. So thanks for listening to our full show yesterday, our Halloween show, which was always so fun. And, you know, before we get to our brand new second date today, we do love to highlight some of your comments. Yes. Amelia said, this might sound creepy. But every day, I sit in front of my laptop waiting until you guys upload a new episode. I'm a 17-year-old entrepreneur in Ireland. And I genuinely can't focus until I hear you guys screaming in my ear. Oh, yeah. Organized chaos in her year.

I love that. We'll keep working hard out there. Amelia, that's rad. Thanks for being here. And your brand new second date starts right now. Sorry, I'd like to invest $5 in your startup company. Oh, there we go. Just want to put that out there. But U.S., right? Oh, darn it. I don't know the conversion. Never mind.

I'm backing out of our deal. Second date update. Welcome back to Brooke and Jeffrey in the morning. Another second date update. And just like many of our male listeners who come on to this segment, today's listener James says he has no idea if he did anything wrong on his first date. I'm sure it was not his fault Yeah, probably not

She's like, well he set my house on fire And he's like, oh wait a minute I forgot to tell him that Don, that's a bad thing But there is a gray area in there That's why we're going to implement This sound Oh

That's an RFA, a red flag alert Oh, I like it Anytime you hear that noise We need to stop what we're doing And discuss could she have maybe taken that The wrong way. Okay. Who's in charge of the sound? You are, Jeff?

That's a red flag. Don't question who's in charge in this room ever, Brooke. I was saying. The power is not in the right hands. Turn off Brooke's mic for the next 10 seconds. Thank you. Let's welcome James to the show. James, how you doing, ma'am? Hey, what's up, guys? You don't have to be afraid of me. I was trying to hear what his voice sounded like before I decided if it was a red flag.

James, I'm scared the button's going to go off. Don't say anything weird. His fingers literally almost. the button. I'm watching it, James. Yeah, no pressure. Just tell us how your date went with, who were we calling today? I went on a date with Chelsea. Chelsea, okay, he remembered the name right away. I almost hit the sound effect, but we're good on that. Do we have a green flag button? There we go. This is going to get annoying if we're doing that. Please. All right. So tell us, how did you meet Chelsea? Okay, so we met on a dating app. Oh, uh-oh. That's not a red flag. That's where people meet now, Jeff.

I agree, but which dating app? We met on Bumble. No, that's a green flag. That's all right. No, hands off the butt. It's a medium. It's a medium. I'm always a little questionable giving girls all the power.

But let's keep going. What did you in Chelsea Bondover when you first met? Yeah, things are like pretty natural right from the start. And one of the things we bonded over was hot sauce. Like, we both love really spicy food. Hot sauce. I heard a Hot Cross and I was like the recorder song. Hot cross buns, yeah.

Hot sauce. And such an easy transition to we need to go get spicy food together. Is that what you did? Did you lead it into like we should try some hot sauce somewhere? Yeah, actually. And we went to this taco place.

Sweet. How did it go? It was great. It was great. There was live music. So it was like, it was a cool setting right off the bat. But it was really loud in there.

And my hearing isn't the best because I've played drums. in my past, like, way too loud. And so my earrings kind of going. So I did ask the waiter if we could, like, move tables so I could hear her better. Yeah, that's good. No. You might come.

Why is that a red flag? You could come across as high maintenance. As a former server, I think I remember people asking this. And sometimes it's actually nice because he's being considerate of her. Now that Jose approves it, I agree. Hit the green flag. Yeah. Jose approved.

Okay, keep going. I want to hear, something worse has to happen on this date. Eventually, you found a table that was quieter. Yeah, it was quieter, and we showed each other pictures of our dogs. We're both dog parents. Aw. That's nice. Okay.

I mean, you guys are viped on all these different levels. I mean, was there anything awkward? Yeah, exactly. Like, I felt like we really connected, and there wasn't anything awkward at all, at least not from what I could tell. Like, she was super cute, and we felt really comfortable talking to each other. I wasn't even, like, pretending and trying to be cool. I was just being myself. Oh, that is so.

Oh, nice. Oh, no. I'm sorry. Jeff's right. Hit the button. No. I'm sorry. That is exactly what people want on a date.

No. I know how it is. Once you get deeper into the relationship, a year, two years in, and the real you comes out, that's when they get wet. That's when everything turns on. That's when you know you're with the right person is when you feel like you can be fully yourself. And that's when your husband spits sunflower seeds all over the house. It's a habit that's annoying. It doesn't define who he is.

It's the real him. Red flag. Okay. Tell us this. Was there any romance happening between you? Any flirtations? Any kissing? There we go.

So unfortunately, there wasn't a kiss, but not because I didn't try. Oh. Did you get turned down? Did she reject you? Not really. Like, she drove me to my car because I kind of parked far away. Yeah. And I'm like a good bit taller than her.

So as I was getting out of her car, like she moved her head toward mine. And then, like, I leaned down and, like, I leaned down. kissed like the top of her head. Oh. Was it awkward or cute? Because a forehead kiss could be cute. It wasn't really her forehead. It was like the top of her head.

It was like hair. Oh my gosh. Yeah, that's a mistake. Got so much hair in my mouth. Yeah. It's like you're kissing your kid before you send them off to school. Yeah, that's not the vibe.

That is an awkward ending. Totally. That's awkward. For sure. And I totally could have buzzed you for not doing valet parking yourself, but I didn't do that. I'm giving you credit there.

Give yourself a green flag, Jeff. What taco spot has Well, hold on, let me give you Yeah, good job, Jeff, for being understanding of other people's clots. I feel really good about myself. I like the flag thing. Anyway, so after the head kiss, how did you two leave it?

I mean, that was it. Like, I just walked back to my car. She drove off. And I haven't heard from her scent. Were you just walking back to your car being like, go off, why did I kiss the top of her? Yeah. That's the worst and you know you blew it. Especially when you could have used tongue and you didn't.

Oh, on her head or what? At least it shows that you're into it. I'm just going to fix your party here with my tongue. There it is. It shows that you wanted it, but you missed. John. Red flag yourself. Yeah. Green flag. Green flag. Green flag for effort. Okay.

And how long has it been since the awkward top of the head kiss? It's been a solid two weeks. Oh. Two weeks. That's a red flag. That's finally one we agree on. Yeah. Any communication at all. No, she hasn't texted me back. That's why I am calling you guys. Hopefully you can help me. Like, did I somehow turn her off?

or offend her or something, I don't know. Well, the head's awkward, but that's not a deal breaker. For sure. Can we not use the sounders when we call her? Well, at that point, she's just going to be telling us what her red flags were. So it's not going to feel good to buzz it. But if she answers the phone on the first try, red flag. She should be, yeah, it's a little bit too over-eager.

It could be a scammer calling her. And I don't trust that. So hopefully she doesn't pick up for a few times, but when she does, Listed for how many rings. Second date update, red flag edition. We'll do it right after this. Hold on. Second date update.

If you're just joining us for the second date update, we played a little game of spot the possible red flags. Why would we not call it red flag green flag? And by we, it was you hitting the button whenever you want. It was a fun time, wasn't it? And several potential flags did come up. One, after they were seated. and James asked the waiter if they could move tables farther away from the live singer.

So that he could actually hear her better. He wanted to listen. Could have come across as he's a high-maintenance guy. Also, maybe she thinks he hates music. What? Nobody wants to eat someone that's anti-music. That is quite a joke. Second possible red flag happened when he went to kiss her,

but she moved so his lips touched the top of her head, aka the proud father kiss. Oh, God. Not a move you want to be pulling, at least not on a first date. And then two full weeks with zero communication from Chelsea, not a good sign. No. So it's all on him, Jeff. Yeah.

The last two I agree with, Jeff. Because even if you don't like a guy at all, you'll at least drunk text him at 2 a.m. one night. Right, Alexis? Yeah, probably. Odds are high. Yeah. We're accidentally like a photo on Insta or something. Exactly.

Slip up will happen. So we are officially, though, we're going to retire the red flag alerts. Oh, wow. That's the last one. It had a good run for at least half a segment. But from now on, let's just try to use our voices to talk and communicate like humans do. Yeah, why are you saying that? It's a group thing.

Let's all agree together. It's just a you thing. Okay. All right, I'm on an island. So I will try to communicate all on my own. And I haven't heard at all from James. James, are you still on the phone? Yeah, I'm here.

Okay. He's listening to your monologue is what he was doing, Jeff. Oh, okay. Green flag for being a good listener That's why you wanted the quieter booth All right, let's just call Chelsea We'll see if she answers Here we go

Hello Hi, are we talking to Chelsea? Yes What is it? Hey Chelsea This is a radio show called Brooke and Jeffrey in the morning Hi Chelsea

We're a fun time Oh, feels forced Okay. Hi. Why are you calling me? This is part of a segment we do called a second date update where we're trying to get some answers for one of our listeners about why he hasn't heard from you since you met up for a date. It was like two weeks ago. Me? Yeah. Yeah. A guy you went out with named James.

Oh. Okay. Remember spicy James? It loves tacos. Yeah. Oh, spicy James. I like that. He emailed us because. he told us about your date, and honestly, he has no idea why you wouldn't be calling him back in the last couple weeks. Wait, why would I even tell you guys? Why would I go into this on the radio? This is so weird. Because he's, like, disappointed. I thought it was, like, such a cool compliment. He told us that he felt like he could fully, totally be his authentic self around you.

Yeah, okay. Sure. Did you feel like that was the case? Yeah, maybe he was his authentic self If that authentic self is like pretty rude Whoa What rude That's so interesting He didn't come across as rude to us at all I felt like he wasn't too timid

Yeah Since we did hear a few things that happened on the date Can we ask was it when he asked to move tables To be far away from the singer that was annoying him That's still why he moved tables, Jed? I don't know I'm leaving it open for her to fill in the play blank. Not leading the witness

at all. No, no. What do you? Chelsea? Was it that? No, that was fine. That didn't bother me. Yeah, because that was sweet. He said he wanted to be able to hear you better so you guys could have some good conversation. Yeah, but it wasn't good conversation because he made me kind of mad. Oh my gosh. Oh, no. He has no idea. Yeah, we didn't hear any like any moment like that come up on your date. So him and I had been getting to know each other for kind of a while on the app. And like, we did. bond over our dogs and we've been telling each other's stories about our pets and on the date

with James I started to tell him a story that I guess I had already told him and forgot and he literally interrupted me and was like sorry to interrupt you but you've already told me this and he wanted me to stop telling my story like that's so rude that's interesting why do you think it's rude though what do you mean why do I think it's rude yes he interrupted me in the middle of my story and basically told me to stop telling the story. Okay. I mean, Brooke, would you like it if you were trying to tell someone a story? And they were like, no, no, no, don't.

I already know that story. I appreciate it when people tell me I'm repeating myself. I tell the same stories all the time. I get that. But it's kind of weird when it's like this is your first face-to-face meeting and they're like, yeah, I've already heard that. Okay, so I could see you being a little annoyed by that. But I can't imagine it being such a big deal.

It's the whole reason you never. want to see him again? Yeah. Big deal or not. It made me mad. I thought it was rude. It gave me the ick. I hate to interrupt, but you did already tell us that you made us mad.

Oh, Jeff. I'll do that. I'm just, we're kind of short on time. It's the only reason why, because I have to let you know that James has been listening to this too on the other line and wants to talk to you. That's a new story. She hasn't heard. Yeah.

New information, right? Wait, he just heard all of that? Yeah. Yeah. Theoretically, if he was listening. James? Hey, Chelsea Hi, oh my God

Are you going to lead with there James Sorry, I had to go this radio route But I just couldn't hear back from you I didn't know what was going on Yeah, James, did you hear the part Where she didn't like that you interrupted her story And said, no, I've already heard that before Yeah, but okay, it was a long story

And I didn't want it to take like another 10 minutes We were trying to have a good conversation. Oh, so the story was too long for you. I was going to say, if it was a long, boring story you already heard, I would cut someone off to, to be honest. No, but you have to think of a more creative way to do it. You thought my story was too long and boring? Not boring. It was just so sad.

Like, when you told me on the app about your dog you grew up with and what happened, like, it was really sad. Okay, but you should let me finish the story. Like, maybe I like to read that. tell my stories sometimes because sometimes you're not listening to the full thing anyway every single time. So you're going to get different Easter eggs every single time I tell it. I want to tell people that. It's true.

I may remember another fact that I forgot last time I told them. And not only that, but if it's a sad story, you don't interrupt somebody who's being emotionally vulnerable. Yeah. Like that I can see, James, where maybe that was the bad timing. But we were trying to have a good fun night. Like, why bring it down? I didn't want that.

Yeah, and you ruined it. Oh. It sounds like she was looking for like a safe space to tell her truth. And you were like, no room for that. And a green flag right now, James, would be you just owning that mistake and apologizing, not trying to make excuses for it. Right. Or downplay her feelings. And Chelsea, can I ask you, is that the reason why at the end of the night you turned your head when he went in for a kiss and just got the top of your skull?

Yeah, actually, after he interrupted me from telling my story, I just got the complete egg, and that was it for me. Kiss my top knot. How does that taste? Yeah. Okay. Are you a person that has ever come back from an ick? No. If you agree to listen to your story in its entirety the next time you met up, just to make up for it?

No, because then I would just be thinking the whole time. Have I told the story or is he bored or like, yeah, it's just not going to work. She keeps making points that I can see what she's saying. Yeah. You know? I feel the same way. There's like nothing I can say here. Maybe say sorry.

Yeah, you will never do it again. I know what I want to say. I want to ask if you two will go out on another date again and we'd be willing to pay for it. But that really comes down to you, Chelsea, if you're willing to give him one more chance. Yeah, no, it's a no for me. I think you should just take it as a learning lesson for his next stage. Okay. Well, Chessie, maybe you should learn, like, how to read a room and not, like, bring the whole room down.

Oh, wow. You're not backing down, James. No, she's being rude to me. She's not even giving me another chance. I think the story is about, like, her childhood dog dying or something. That's what it sounds like. No, I rescued him from a tree, and then he fell and died. Oh, my God.

Oh, wow. Brooke, why would you even bring that up? No, I'm sorry. Brooke, red flag for the segment. I deserve that one. Yes, don't ask any questions ever again. Brooke and Jeffrey in the morning. No one can resist a rule of culture.

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connections into something bigger. Download Bumble and start your love story. Here we go. Hey, I'm Cal Penn, and on my new podcast, Here We Go Again, we'll take today's trends and headlines and ask, why does history keep repeating itself? You may know me as the second hottest actor from the Harold and Kumar movies, but I'm also an author, a White House staffer, and as of like 15 seconds ago, a podcast host. Along the way, I've made some friends who are experts in science,

politics, and pop culture. And each week, one of them will be joining me to answer my burning questions. Like, are we heading towards another financial crash, like in 08? Is non-monogamy back in style? And how come there's never a gate ready for your flight when it lands like two minutes early? We've got guests like Pete Buttigieg, Stacey Abrams, Lili Singh, and Bill Nye. When you start weaponizing outer space, things can potentially go really wrong. Look, the world can seem pretty scary right now.

because it is. But my goal here is for you to listen and feel a little better about the future. Listen and subscribe to here we go again with Cal Penn on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. All right, listen, I'm sorry I had to bring back the red flag alert out of retirement at the end there,

but Brooke crossed the line. We all agreed. Yeah, you had to get her. You had to zap her with it. No one else wanted closure on what happened with the door. No, I don't think we needed any more details. I kind of trust that there was a reason to cut the story off.

Yeah, yeah. It was a little bit hard because I felt like actually both of them had decent points in the conversation. I mean, if it was a debate, like in high school, I think she won by one point. Yeah. You know what I mean? It was close. Yeah, she came out on top. But I also think that they probably should have gone out again.

Because it felt like something you could definitely work through if you talked about it. Yeah, totally. I think this girl has zero patience. She should have brought it up during the date and said, sorry, I think it's rude for you to interrupt me telling my story again. and they could have quashed it right there and moved on. Nobody likes doing that, Jeff. That's confrontation. That's true.

But if you want to hear all of our stories, the second date ones, our awkward Tuesdays, all of our content is up online. You can check it out wherever you get your podcast at Brooke and Jeffrey. Johnny Knoxville here. Check out Crimeless, Hillbilly Heist, my new true crime podcast from Smartless Media, campside media, and big money players.

It's the true story of the almost perfect crime and the Nimrods who almost pulled it off. It was kind of like the performance. storm in a sewer. That was dumb. Do not follow my example. Listen to Crimeless, Hillbilly Heist on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. I live below a cult leader, and I fear I've angered her. Wait a minute, Sophia. How do you know she's a cult leader? Well, Dakota, luckily it's I'm not afraid of a scary story week on the OK Storytime podcast. So we'll find out soon. This person writes, my neighbor has been blasting music every day.

and doing dirt rituals. And now my ceiling is collapsing. I try to report them, but things keep getting weirder. I think they might be part of a cult. Hold up. A real life cult? And what is a dirt ritual? No clue, Dakota. Find out how it ends.

Listen to the OK Storytime podcast on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hey, I'm Cal Penn. And on my new podcast, here we go again. We'll take today's trends and headlines and ask, why does history keep repeating itself? Each week, I'm calling up my friends, like Bill Nye, Lily Singh, and Pete Buttigieg to talk about everything from the space race to movie remakes to psychedelics. Put another way, are you high? Look, the world can seem pretty scary right now. But my goal here is for you to listen and feel a little better about the future.

Listen and subscribe to here we go again with Cal Penn on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Two rich young Americans move to the Costa Rican jungle to start over, but one of them will end up dead and the other tried for murder three times. It starts with a dream, a nature reserve and a spectacular new home. But little by little, they lose it, they actually lose it. They sort of went nuts. Until one night, everything spins out of control. Listen to Hell in Heaven on the IHeart Radio app.

Apple Podcasts, or wherever you get your podcasts. The Big Take podcast from Bloomberg News keeps you on top of the biggest stories of the day. My fellow Americans, this is Liberation Day. Stories that move markets. Chair Powell opened the door to this first interest rate cut. Impact politics, change businesses. This is a really stunning development for the AI world

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