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Jeff
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Brooke
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Jeff
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Chelsea
You did it. You made it through the Halloween weekend. 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 is always so fun. Fun.
Jeff
Yeah.
Chelsea
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.
Jeff
Organized chaos in her ear.
Chelsea
I love it. Well, keep working hard out there, Amelia. That's rad. Thanks for being here. And your brand new second date starts right now.
Jeff
Sorry, I'd like to invest $5 in your startup company. Just want to put that out.
Chelsea
But us, right?
Jeff
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 onto this segment, today's listener, James, says he has no idea if he did anything wrong on his first date.
Chelsea
I'm sure it was not his fault.
Jeff
No, probably not. And then she's like, well, he set my house on fire. And he's like, oh, wait a minute. I forgot.
Chelsea
You forgot to tell him that, Dawn.
James
That's a bad thing.
Jeff
But there is a gray area in there. That's why we're gonna implement this sound. Oh, that's an rfa. A red flag alert.
Chelsea
Oh, I like it.
Jeff
Anytime you hear that noise, we need to stop what we're doing and discuss. Could she have maybe taken that the wrong way?
Chelsea
Okay, who's in charge of the sound? You are, Jeff.
Jeff
That's a red flag. Don't question who's in charge in this room ever.
Chelsea
Brooke saying, the power is not in the right hands.
Jeff
Turn off Brooks Mike for the next 10 seconds. Thank you. Let's welcome. Let's welcome James to the show. James, how you doing, man?
James
Hey, what's up, guys?
Jeff
You don't have to be afraid.
Chelsea
I just tried to hear what his voice sounded like before I decided if it was a red flag to hit the button. I'm scared the button's gonna go off.
Jeff
Don't say anything weird. His fingers literally on the button. Yeah, no pressure. Just tell us how your date went with who calling today.
James
I. I went on a date with Chelsea.
Jeff
Chelsea. Okay. He remembered the name right away. I almost hit the. Hit the sound effects, but we're good on that. Do we have a green flag button?
James
There we go.
Chelsea
This is going to get annoying if we're getting styled. Please.
Jeff
All right, so tell us how. How did you meet Chelsea?
James
Okay, so we met on a dating app.
Chelsea
That's not a red flag. That's where people meet now, Jeff, I.
Jeff
I agree, but which dating app?
James
We met on Bumblebee.
Chelsea
No, that's a green flag. That's all right.
Jeff
No flag. 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 and Chelsea bond over when you first met?
James
Yeah, things were, 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.
Jeff
I heard hot cross, and I was like the recorder song. We all have hot cross buns. Yeah. Hot sauce. Hot sauce is awesome.
Chelsea
And such an easy transition to we need to go get spicy food together.
Jeff
Is that what you did? Did you lead it into, like, we should try some hot sauce somewhere?
James
Yeah, actually. And we went to this taco place.
Chelsea
Sweet. Nice.
Jeff
How did it go?
James
It was great. It was great. There was live music, so it was like.
Chelsea
That's fun.
James
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 played drums in my past, like, way too loud. And so my earring's kind of going. So I did ask the waiter if we could, like, move tables so I could hear her better.
Chelsea
Yeah, that's good.
Jeff
You might come.
Chelsea
Is that a red flag?
Jeff
You could come across as high maintenance. No. Former server. I think I remember people asking this. And sometimes it's actually nice because he's being considerate of her.
Chelsea
Totally.
Jeff
Now that Jose approves it. I agree. Hit the green flag. Yeah, Jose. Approved. Okay, keep going.
Chelsea
I want to hear something. Worse has to happen on this date eventually.
Jeff
You found a table that was quieter.
James
Yeah, it was quieter. And I like. We showed each other pictures of our dogs. We're both dog parents.
Jeff
Aww, that's nice.
Chelsea
Okay, so, I mean, you guys are vibing on all these different levels. I mean, was there anything awkward?
James
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.
Chelsea
Oh, that is so nice.
Jeff
Oh, no, Jeff's right. Hit the button. I'm sorry.
Chelsea
That is exactly what people want on a date.
Jeff
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 everything turns on.
Chelsea
That's when you know you're with the right person, is when you feel like you can be fully yourself.
Jeff
And that's when your husband spits sunflower seeds all over the house.
Chelsea
It's a habit. That's annoying. It doesn't define who he is.
Jeff
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.
James
So, unfortunately, there wasn't a kiss, but not because I didn't try.
Chelsea
Oh, did you get turned down?
Jeff
Did she reject you?
James
Not really. Like, she drove me to my car because I kind of parked far away, 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 I leaned down and kissed, like, the top of her head.
Brooke
Oh.
Jeff
Was it awkward or cute? Because a forehead kiss could be cute.
James
It wasn't really her forehead. It was, like, the top of her head, like hair.
Jeff
Oh, my gosh. Yeah.
Chelsea
That's got so much hair in my mouth. Yeah.
Jeff
It's like you're kissing your kid before you send them off to school. That's not the vibe.
Chelsea
That is. That is an awkward ending.
Brooke
Totally.
Jeff
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.
Chelsea
Give yourself a great taco spot. Has very.
Jeff
Yeah. Good job, Jeff, for being understanding of other people's clubs. I feel really good about myself. Flag thing. Anyway, so after. After the head kiss, how did you two leave it?
James
Oh, I mean, that was it. Like, I just walked back to my car. She drove off.
Jeff
Oh.
James
And I haven't heard from her since.
Chelsea
Were you just walking back to your car being like, God, why did I kiss the top of her head?
Jeff
The worse. And you know, you blew it. Especially when you could have used tongue and you didn't. At least it shows that you're into it. I'm just gonna fix your part here with my tongue. There it is. It shows that you wanted it, but.
Chelsea
You missed red flag yourself.
Jeff
Green flag forever. And how long has it been since the awkward top of the head kiss?
James
It's been a solid two weeks.
Chelsea
Wow, that's a red flag. Finally, when we agree on any communication at all.
James
No, she hasn't texted me back. That's why I'm calling you guys. Hopefully you can help me. Like did I somehow turn her off or offend her or something? I don't know.
Jeff
Well, the head's awkward but that's not a deal breaker for sure.
Chelsea
Not use the sounders when we call her.
Jeff
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, that's a little bit too over eager. It could be a scammer call. I don't trust that. So hopefully she doesn't pick up for a few times, but when she does, listen 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.
Chelsea
Why would we not call it Red flag Green flag? And by we it was you hitting the button whenever you want.
Jeff
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 synchronous.
Chelsea
So that he could actually hear her better. He wanted to listen.
Jeff
Could have come across as he's a high maintenance guy. Also, maybe she thinks he hates music. Nobody wants to date someone that's anti music. Second possible red flag happened when he went to kiss her, but she moved. So his lips touch the top of her head. AKA the proud father kiss. 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. So it's all.
Chelsea
Yeah, the last two. I agree with Jeff because even if.
Jeff
You don't like a guy at all, you'll at least drunk text him at 2am One night. Right, Alexis?
Chelsea
Yeah, probably. Odds are high. Or accidentally like a photo on Insta or something.
Jeff
Exactly. Slip up will happen. So we are officially though, we're going to retire the red flag alert. That's the last one. It had a good run for at least half a segment, but from now on let's try. Just try to use our voices to talk and communicate like humans do. You're talking about.
Chelsea
Yeah. Why are you saying that?
Jeff
It's a group thing. Let's all agree together.
Chelsea
Just a you thing.
Jeff
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. Yeah. James, are you still on the phone?
James
Yeah, I'm here.
Chelsea
Okay.
Jeff
Okay.
Chelsea
He's listening to your monologue is what he was doing. Yeah.
Jeff
Oh, okay. Green flag for being a good listener.
Chelsea
There we go. That's why you wanted the quieter booth.
Jeff
All right, let's just call Chelsea. We'll see if she answers. Here we go.
Chelsea (on phone)
Hello?
Jeff
Hi. Are we talking to Chelsea?
Chelsea (on phone)
Yes. Who's this?
Jeff
Hey, Chelsea. This is a radio show called Brooke and Jeffrey in the Morning.
Chelsea
Hi, Chelsea.
Jeff
We're a fun time.
Chelsea
Oh, feels forced.
Chelsea (on phone)
Okay. Hi. Why are you calling me?
Jeff
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.
Chelsea
It was, like, two weeks ago.
Brooke
Me?
Chelsea
Yeah.
Jeff
Yeah, a guy you went out with named James.
Chelsea (on phone)
Oh, okay.
Chelsea
Remember Spicy James that loves tacos?
Jeff
Oh, Spicy James. I like that.
Chelsea
Yeah, thanks.
Jeff
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.
James
Wait, why?
Chelsea (on phone)
Why would I even tell you guys? Why would I go into this on the radio? This is so weird.
Chelsea
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.
Chelsea (on phone)
Yeah, okay, sure.
Jeff
Did you feel like that was the case?
Chelsea (on phone)
Yeah. Maybe he was his authentic self. If that authentic self is, like, pretty rude.
Jeff
Whoa.
Brooke
What?
Jeff
Rude?
Chelsea
That's so interesting. He didn't come across as rude to us at all.
Jeff
I felt like he was just 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?
Chelsea
That's not why he moved tables down?
Jeff
I don't know. I'm leaving it open for her to fill in the blank.
Chelsea
Not leading the witness at all.
Jeff
No, no. What do you. Chelsea, was it that.
Chelsea (on phone)
No, that was fine. That didn't bother me.
Chelsea
Yeah, because that was sweet. He said he wanted to able to hear you better so you guys could have some good conversation.
Chelsea (on phone)
Yeah, but it wasn't good conversation because he made me kind of mad.
Chelsea
Oh, my God. He has no idea.
Jeff
Yeah, we didn't hear any, like, any moment like that come up on your date.
Chelsea (on phone)
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 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.
Chelsea
That's interesting. Why do you think it's rude, though?
Chelsea (on phone)
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.
Jeff
Oh, okay.
James
Okay.
Jeff
I mean, Brooke, would you like it if you were trying to tell someone a story and they were like, no, no, no, no, don't. I already know that.
Chelsea
I appreciate it when people tell me I'm repeating myself. I tell the same stories all the time.
Jeff
I get.
Chelsea
I get it.
Jeff
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.
Chelsea
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.
Jeff
Yeah.
Chelsea (on phone)
Big deal or not, it made me mad. I thought it was rude.
James
It gave me the ick.
Jeff
I ha. Interrupt. But you did already tell us that you made us mad. I'm just. We're kind of short on time is 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.
Chelsea
That's a new story she hasn't heard. Yeah.
Jeff
New information, right.
Chelsea (on phone)
Wait, he just heard all of that?
Chelsea
Yeah.
Jeff
Yeah. Theoretically, if he was listening. James.
James
Hey, Chelsea.
Chelsea (on phone)
Hi. Oh, my God.
Chelsea
What are you gonna lead with there, James?
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.
Chelsea
And that's not why she's upset.
Jeff
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.
James
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.
Chelsea
Don't say that, James.
Jeff
So the story was too long for y'? All?
Chelsea
I was gonna say, if it was a long, boring story you already heard.
Brooke
I would cut someone off, too, to be honest.
Chelsea
But you have to think of a more creative way to do.
Chelsea (on phone)
Yeah, you thought my story was too long and boring.
James
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, and I didn't want.
Chelsea (on phone)
Okay, but you should let me finish the story. Like, maybe I like to retell 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.
Jeff
That true. I may remember another fact that I forgot last time I told them.
Chelsea
And not only that, but if it's a sad story, you don't interrupt somebody who's being emotionally vulnerable like that. That I can see, James, where. Maybe that was the bad timing, but.
James
We were trying to have a good, fun night. Like, why bring it down? I didn't want that.
Chelsea (on phone)
Yeah, and you ruined that.
Jeff
So it sounds like she was looking for, like, a safe space to tell her truth, and you were like, no room for that.
Chelsea
And a green flag right now, James, would be you just owning that mistake and apologizing, not trying to make excuses for it.
Jeff
Right.
Chelsea
Or downplay her feelings.
Jeff
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?
Chelsea (on phone)
Yeah, actually, after he interrupted me from telling my story, I just got the complete ache, and that was it for me.
Jeff
Kiss my top. Not.
Chelsea
Okay.
Jeff
Can you.
Chelsea
Are you a person that has ever come back from an ick.
Chelsea (on phone)
No.
Jeff
If he agreed to listen to your story in its entirety the next time you met up, just to make up for it, I mean, would that.
Chelsea
No.
Chelsea (on phone)
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 gonna work.
Chelsea
She keeps making points that. I can see what she's saying.
James
Yeah, you know, I know. I feel the same way. There's, like, nothing I can say here.
Chelsea
Maybe say, sorry.
Jeff
Yeah.
Chelsea
You will never do it again.
Jeff
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's really comes down to you Chelsea, if you're willing to give him one more chance.
Chelsea (on phone)
Yeah, no, it's a no for me, but I think he should just take it as a learning lesson for his next date.
Chelsea
Okay, well, Chelsea, maybe.
James
Maybe you should learn, like, how to read a room and not like, bring the whole room down.
Jeff
You're not backing down? No.
James
She's being rude to me. She's not even giving me another chance.
Chelsea
This theory is about, like, her childhood dog dying or something. That's what it sounds like.
Chelsea (on phone)
No, I rescued him from a tree and then he fell and died.
Chelsea
Oh, my God.
James
Wow, Brooke.
Jeff
Why would you even bring that up?
James
Brooke.
Chelsea
Yeah.
Jeff
Red flag for the segment.
Chelsea
I deserve that one.
Jeff
Yes. Don't ask any questions ever again. Brooke and Jeffrey in the morning. You need to check out legends.com today. Legends is a free to play social casino and sportsbook with with all of the games that you know and love. They even have Plinko and live blackjack. And that's L E G E N D z dot com. Whether you're a seasoned player or just starting out, their games are designed to entertain and thrill. The best part is you get free coins every day so you can play for free. And redemption to your bank account is instant. It's legit. And new players get an exclusive welcome bonus. Join thousands of players on legends with a Z.com today. No purchase necessary. Legends International void. We're prohibited by law. 18 plus terms and conditions apply.
Brooke
I don't know about you guys, but I love to buy gifts. I love it so much. I love it so much more than getting gifts. But the one thing that I do love, especially when it comes to my daughter, is getting matching things. I know it's such a cliche, but I love it so much. So I have the perfect brand for you. Pandora Jewelry can make their holiday unforgettable with the gift that says it all from Pandora Jewelry. A gift that tells a story and shows you know, theirs that doesn't just sparkle, but speaks from new festive charms to forever rings and personal engravings. This season, give a gift that's perfectly theirs. Whether you're shopping for a shiny surprise for your significant other, matching bracelets to celebrate your friendship. Or a heartfelt gift for a family member. Say more this holiday season with Pandora. Shop now@pandora.net or visit your closest Pandora store.
Jeff
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 agree we needed that. Yeah, you had to get her. You had to zapper with.
Chelsea
No one else wanted closure on what happened?
Jeff
No, no, I don't think we needed any more details.
Chelsea
Kind of trusted there was a reason he cut the story off.
Jeff
Yeah, it was a little bit hard because I felt like actually both of them had decent points in the conversation.
Chelsea
I mean, if it was a debate like in high school, I think she won by one point.
Jeff
Oh, yeah.
Chelsea
You know what I mean? It was close debates.
Jeff
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.
Chelsea
I think this girl has zero patience.
Jeff
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.
Chelsea
Nobody likes doing that, Jeff.
Jeff
Yeah, that's confrontation.
Chelsea
Yeah, that's true.
Jeff
But if you want to hear all of our stories, the second date ones are awkward Tuesdays. All of our content is up online. You can check it out wherever you get your podcasts at. Brooke and Jeffrey. Hey, it's Ryan Seacrest for Albertsons and Safeway this fall. Take care of the little ones in the family with Baby Club Savings now through November 4th. Spend $25 on select Baby Club products and save $5. Shop for items like Pedias shore bottles, Pedialyte powder packs, Huggies baby wipes, Huggies diapers, Gerber puffs and Gerber pouches. And save $5 when you buy $25 or more on participating products. Offer ends November 4th. Restrictions apply. Offers may vary. Visit Albertsons or Safeway Details.
Chelsea
Every now and then I rinse it out and I need yummy rinse tonight.
Jeff
And I need it more My kid went and the smell never leave.
James
I.
Jeff
Don'T know what to do I'm always in the dark, the sweat and that short smells like a dark I'm down here. Downy Rinse fights stubborn odors in just one wash when impossible odors get stuck in. Hello, America's sweetheart. Johnny Knoxville here. I want to tell you about my new true crime podcast, Crimeless Hillbilly Heist from Smartless Media, Campside Media and big money Players. It's a wild tale about a gang of high functioning nitwits who somehow pulled off America's third largest cash heist. Kind of like Robin Hood, except for the part where he steals from the rich and gives to the poor. I'm not that generous. It's a damn near inspiring true story for anyone out there who's ever shot for the moon, then just totally muffed up the landing. They stole $17 million and had not bought a ticket to help him escape.
Chelsea (on phone)
So we're sitting like, oh God, what do we do?
Brooke
What do we do?
Jeff
That was dumb. People, do not follow my example. Listen to Crimeless Hillbilly Heist on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Chelsea
I live below a cult leader and I fear I've angered her.
Jeff
Wait a minute, Sophia, how do you know she's a cult leader?
Chelsea
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.
Jeff
Rituals, and now my ceiling is collaps to report them.
Chelsea
But things keep getting weirder. I think they might be part of a cult.
Jeff
Hold up a real life cult? And what is a dirt ritual? No clue, Dakota.
Chelsea
Find out how it ends. Listen to the OK Storytime podcast on the iHeartRadio app, Apple Podcasts, or wherever.
Jeff
You get your podcasts. Hey, I'm Kalpen, 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, Lilly 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 Kal Penn on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Podcast: Brooke and Jeffrey: Second Date Update
Episode: "Second Date Update: Red Flag Test"
Date: November 3, 2025
In this episode, Brooke, Jeff, and the team tackle another ‘second date’ mystery, helping listener James uncover why Chelsea has not responded after their promising first date. Employing their signature banter and a playful “red flag alert” sound effect, the crew analyzes every moment of James and Chelsea’s date to find out what went wrong—was it a small misstep, or a true deal-breaker? The episode dives deep into dating etiquette, communication mishaps, and the power of first impressions.
This episode is a classic “Second Date Update” blend of awkward, funny, and revealing. It shines a light on the small communication pitfalls that can make or break a budding romance—especially when expectations about listening and empathy diverge. The playful “red flag” game keeps the tone light, but the conversation also explores deeper questions about boundaries, authenticity, and forgiveness in dating.
Despite James’s nerves and honest intentions, one moment of blunt interruption proved to be an “ick” that Chelsea couldn’t get past—a small misstep with big consequences when mutual vulnerability is on the line.
For more laughs and cringe-worthy moments, catch "Second Date Update" on Brooke and Jeffrey wherever podcasts are found.