Brooke and Jeffrey: Second Date Update - Second Date Update Classic: Mistah Secure

Episode Date: November 23, 2024

Typically on a first date, you’re supposed to do something fun and not invite someone to your work... But the guy in today’s Second Date did the second option and now he’s calling us for help fixing his love life!See omnystudio.com/listener for privacy information.

Ugh, we're so done with New Year, New You. This year, it's more you on Bumble. More of you shamelessly sending playlists, especially that one filled with show tunes. More of you finding Gemini's because you know you always like them. More of you dating with intention because you know what you want. And you know what? We love that for you. Someone else will too. Be more you this year and find them on Bumble.

Jon Stewart is back at The Daily Show, and he's bringing his signature wit and insight straight to your ears with The Daily Show Ears Edition podcast. Dive into Jon's unique take on the biggest topics in politics, entertainment, sports, and more. Joined by the sharp voices of the show's correspondents and contributors. And with extended interviews and exclusive weekly headline roundups, this podcast gives you content you won't find anywhere else.

Ready to laugh and stay informed? Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. People, my people, what's up? This is Questlove. Man, I cannot believe we're already wrapping up another season of Questlove Supreme. Man, we've got some amazing guests lined up to close out the season, but, you know,

I don't want any of you guys to miss all the incredible conversations we've had so far. I mean, we talked to A. Marie, Johnny Marr, But, you know, I don't want any of you guys to miss all the incredible conversations we've had so far. I mean, we talked to A. Marie, Johnny Marr, E., Jonathan Sheckner, Billy Porter, and so many more. Look, if you haven't heard these episodes yet, hey, now's your chance. You've got to check them out. Listen to Questlove Supreme on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. 1.4 billion dollars in NFL quarterback contracts. The untold stories behind the biggest deals in football history.

I'm A.J. Stevens, Vice President of Client Strategy at Athletes First, introducing the Athletes First Family Podcast, the quarterback series. My co-host Brian Murphy, Athletes First, introducing the Athletes First Family Podcast, the quarterback series. My co-host Brian Murphy, Athletes First CEO, and I are sitting down with the agents who have negotiated contracts for Justin Herbert, Deshaun Watson, Dak Prescott, Tua Tugnavailoa, and Jordan Love. Listen to Athletes First Family Podcast on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. What if you asked two different people the same set of questions? Even if the questions are the same, our experiences can lead us to drastically different answers. I'm Minnie Driver, and I set out to explore this idea in my podcast,

and now, Minnie Questions is returning for another season. We've asked an entirely new set of guests our seven questions, including Jane Lynch, Delaney Rowe, and Cord Jefferson. Listen to mini questions on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Seven questions, limitless answers. Second date update. This happens every so often,

but sometimes a listener will do a second date update with us that doesn't end with a yes. No, just every so often. But the thing is, they're so impressed by us, specifically me and my efforts to jumpstart their love lives, that they're willing to call back and give it another go. You know, you don't have to do mouth-to-mouth anymore with CPR. But I like to do that. That's why Justin has reached out to us once again. He was on a few months back, and last time, the lady he went out with was not impressed because she showed up an hour late to dinner but said Justin wasn't man enough to be mad about it and cancel.

What? Oh, I think I remember this. It was really weird, and that call definitely crashed and burned, but we promise to try and do better for Justin this time. So, Justin, welcome back. Hey, thank you guys for having me. Oh, man. How long did you wait for your date to show up this time, Justin?

No, she actually came right on time this time. Another test, and you failed it, I'm sure. You're supposed to get up and leave and make her wait now. I think that shows improvement. And I heard that you've been actually doing a little bit of research since the last time you were on with us. Yeah, I feel like the learning process never really ends. I'm always trying to better myself, you know? It's so deep.

That is so deep, Justin. I heard about this book called Attached. Are you familiar with it? Attached? I don't know. Reading is not on the top of the list of hobbies for this group. But tell us about it. What is Attached about? So this book basically talks about how most people come into three different psychological categories while dating. Wow.

Okay. Secure, where you can communicate openly. I can be like, hey, I know you're busy, but I just kind of get nervous when you don't text back. Could you text me? Just let me know, even if it's just like a little thumbs up or something. Oh, it's like the type of communicator you are? Exactly.

Those three groups, they're secure. Yeah. The other two categories are anxious and avoidant oh god anxious people are like the super needy ones where it's just like no you got to text me and if you don't hear a text back you're texting them like 20 times like where are you where are you jose is this registered for you i don't know if i'm necessarily anxious in that sense but in real life i'm anxious a lot yeah and then what's the other one again the last one is avoidant where like if things start getting real they'll push apart a little

bit like they want distance they don't want to be smothered or anything okay can you be more than one like i feel like i'm the first two combined you have to read the book and find out oh no i'm just gonna wait for the movie to come out sounds really like a fun movie jeff the netflix one if they can make it really short because my attention span isn't great okay so which which one are you justin so i'm secure with traits of anxious and um so you can be more than one okay okay so what how did that change dating um i'm just really open and communicative about what i'm expecting how i feel no more games of like like you know with the girl who was late i could just be like hey you're late that made me feel this way what's going on

you know just talk about it so wait did we go on a date or are we just hearing about how your love life has improved which is great this is just a therapy session for everybody in the room. Or Justin wrote this book and he's trying to sell coffee. Exactly. So how does all this relate to your new and improved dating life? So I put this on my dating profile where I said,

secure attachment styles only, and it didn't really get me any clicks. Oh, yeah. Shocking. Yeah. But then I put that smiley emoji with like the sweat drop coming on the forehead you know and that got me a few then okay so who who matched with your secure people only demand with this

wonderful woman named callie she's an interior designer absolutely very very secure okay and i kind of wanted to have her see what i did um i don't even know if we spoke about this last time i'm a professional rapper like at least part-time what what how did that not come up because like you know unless you're super duper famous people just presume you're crap oh jack okay yeah you invited to, what, watch you rap somewhere? Yeah, to a show that I was doing. And we hung out before we got to know each other. And then it was time for me to go on stage.

And I had a couple songs that night. So I did those. The crowd was really into it. Like, I was a little nervous, you know, because sometimes the crowd might not be into it. Yeah, I don't have a bad sense on your date. Yeah, but when I got off stage, she said it was awesome. Oh, good. And then, like, people were coming up to me just, like, taking photos and things of that sort, which is always fun.

Oh, damn. But I kind of worried, like, maybe my lyrics were a little bit too vulgar, but that's kind of also, like, the nature of the beast of being an artist. Too vulgar? Oh, boy. I mean, you're a rap artist. Yeah. Unless you're Will Smith. What type of rapper are you?

He didn't swear once. She did say it was awesome, but I remember there was a point where I made eye contact with her while I was rapping. And I noticed her eyes were kind of big. I don't know if she thought this, but my read was like, she's like, what the hell did he just say? Oh, boy. Can you give a subject material on that one? Like, can you get to know anything? Some of it gets political.

Some of it is just, you know, like... Okay. That might widen some eyes. What's up, y'all motherfucking Democrats? It's Mr. Secure up in the building. All right, well... Okay, got your openers for you in the next show. I wanted to stay a little longer and hang out more but like while the people were taking photos she was just like i gotta go it was

so great seeing you and then oh she bounced yeah i had a tough time getting another date and i really really did like her you know way more than the girl who made me wait an hour yeah but this time you kind of made her wait yeah same thing, we'll see what Callie has to say because we're going to drop some beats right here just for you. And then we're going to come back and get your second date update right after this. All right. Sounds great. All right. Hold on, man.

He's smart. He's sexy. And he's totally secure i'm talking about our listener justin who's back doing a second date update for the second time on our show because we failed him the first go around but this time justin went out with a woman named callie who he described as also secure and all right like that's that's her attachment or whatever it is it's a good thing yeah okay and she got to see him in his element spitting mad bars at a rap show weird part was while he was taking photos with fans after his performance callie suddenly ducked out said she had to go

yeah and we don't know why i'm sure brooke has some theories for why i don't know maybe she just was sick of being there i mean it's a long time to go to a rap show and then to sit and all his little fans coming up yeah your date like being on stage and not with you you see you're by yourself and then you're by yourself more i can compare if you're like literally like as a comedy show you're doing meet and greet and your date is just watching yeah it's just boring like you just yeah you can totally i don't i didn't get that at all i mean i didn't want to be rude to the people who come up you know i'm not like a kanye west or anything they came to the show i'm gonna take a second to say hello back

no we're not saying that that's bad it's just that like on a first date that may be you know it kind of just sucks from her perspective you know but everyone else gets time with you but her real stars don't take photos with their fans because they're past that yeah that's true maybe it came across as kind of needy that you need your fans in order to seem cool he said he was secure but maybe this whole time you're reading your maybe yeah what's the other ones anxious i have traces anxiousness i said that okay there it is maybe of anxiousness. I said that. Okay. There it is. Maybe the anxiousness turned her off, but we're going to call her and find out.

Let's dial Callie's number and see what she has to say. All right. All right. Here we go. Hello? Hey, is this Callie? This is her. Secure, excuse me my name is jeff i heard that you were secure uh sorry my name is jeff from the radio show brooke and jeffrey in the morning there it is i which radio show i don't even know

don't worry about it we have a podcast too maybe you listen to that i don't think i've heard of you guys okay what's this about well we do a segment on this show called second date update and we're trying to help one of our listeners get a hold of you because you went out with him the other night and now you're avoiding him his name's justin oh well you guys went to a rap show? Yeah, I remember him. How much do you guys know? Well, we know that he is an up-and-coming rap star, and he took you to his show.

But he said you left while they were doing a meet-and-greet. Yeah, I did. So I didn't really enjoy him very much. Oh. Oh, like the show you didn't enjoy? No, the show was fine. He's actually a really talented rapper. I didn't mind the show at all.

I thought he was pretty good. You liked him on stage, but you didn't like him on stage. Is that what you're saying? His on-stage persona is better. Yeah, he lost me, I mean, before the rap. We were talking before the show he just kept going on about the book the attachment theory book yeah you mentioned that was it too much for you he just wouldn't let it go like and on a first date the first time i'm ever talking to

him he's like psychoanalyzing me and like yeah we're trying to figure out what personalities match and i'm like i just find out if i click with you if you're just having a conversation about what we like to do like i mean it's cool to click with someone in their values but you don't normally figure that out on date one and like just based on this one theory like it was boring to just talk about that and only that it's like people who won't date like other horoscope signs and you didn't feel like i mean you weren't interested you knew from the beginning that you weren't going to give him another shot well i knew after about 30 minutes of him talking about this over and over that i was bored 30 minutes you went on for 30 minutes of that attachment theory? We talked to him for like five minutes about it and it felt like a lot.

I can't imagine 30 minutes of that conversation. I mean, at least he's passionate about it. Passion is a good quality to have about things. But he wouldn't let it go. And it was like a tedious breakdown of the book. Like all the categories, who they match with. And, you know know deciding that okay i'm secure and he's secure i was like okay but only one of us is boring yeah

that really hurts it's gotta hurt to hear i don't know maybe justin's secure enough to take it in stride because cal i need to tell you he's on the other line listening right now and wants to talk to you. It's a secure line. Yes, it is. You had him on the whole time? Yeah. He heard all of that? He did. That's alright. Justin? He needed to hear that. You there? Hey, Cali.

You hear how secure he sounds? I'm so tired of that word. You could be secure. Justin, I didn't want to be mean to you. I just, you need to know that this strategy doesn't work. Like women aren't into that. It's not a strategy. I just really liked the book I read and I thought you were enjoying the conversation, like the vibe that I was getting.

You know, I'm sorry I misread the situation. I didn't know maybe it was because I was pre-show jitters or something and I missed the signs. But I don't think you were reading that situation right at all. And it's just not a good strategy. Like it's day one. We're supposed to just talk about, you know, the trivial things, likes and dislikes, what pizza toppings you eat, what Netflix shows you're currently binge watching. Well, he's talking about his favorite book. You know, it's not Fifty Shades shades of gray but at least it's like adjacent i'm sorry i'm not basic i don't want to go on multiple dates and talk about like pizza toppings like do you know how many girls i

go out with like i'm trying to find somebody who's special hey some people can talk about pizza toppings for 30 minutes thank you very much Justin, that just came off a little hot, man. Yeah, that was a little. Came off confident. I don't think so. The first dates get so repetitive. I thought we connected on something deeper, you know? But it sounds like you weren't listening to her.

It sounds like you were just like monologuing about a book that you read. You know, I thought she was into it, and I apologize. I didn't mean to be boring. I got a B word for you, and it's not boring. Whoa. Wait. Whoa. What?

She said you were a good rapper. Why would you mean me? I'm a dope rapper. I'm one of the best to ever do it. Oh. Okay. Okay. That's happening.

Well, remember, you're taking pictures with fans, and that's Jeffrey Proove. Yeah, you don't see Kanye taking pictures with anybody. Callie, let's just pretend that you didn't hear him call you the other B word. Wow. Can you see how it was maybe a little bit your fault because you were encouraging him. He said that she seemed,

she seemed interested. Yeah, that can definitely not be blamed on me just because I didn't step in and say, hey, stop talking about this now.

You're boring me. Like that would have been extremely rude. That would have been a very helpful clue to him that he needs to change the subject. And if he was really secure, he would have been fine would have been a very helpful clue to him that he needs to change the subject and if he was really secure he would have been fine with it i just think he's not the best at reading people because it was very clear that i was bored and you know when you say to somebody like oh cool like four times in a row luckily

it means you're not really there luckily i'm very good at reading people and reading situations and i'm sensing a vibe right here i am i'm feeling the love connection happening and that's why i'd like to offer to send callie out on another date with justin we'll pay for it i'm gonna stop you right there i thought this girl was secure i'm getting so much avoidant and anxious vibes from her i don't think i'm ready for a second date you know i'm still sensing some vibes going on i not only there's something we agree on okay yeah i not only misread that conversation i misread her entire profile and who she was as a human being so yeah whoa hard pass okay so i'm getting a sense this is more of just a hookup one

night thing oh okay she's not gonna stay the night she's just gonna be in and out before the sun even comes up he said hard pass unless it's the name of his album i don't think okay it's a good album name i'm just trying really hard because i don't want to go 0 for 2 with Justin here. You guys, this is not your fault. I mean, I love you guys. I love the show. I love that you, like, are taking the time to help me. You're 0 for 1.

Betting 500, it's pretty good. Hey, 0 for 1 is still betting 0. I'm calling it 50-50. We have definitely never gotten on base. It's a victory in my book. Congratulations, Justin. I'm calling it 50-50. Okay. We have definitely never gotten on base with him. It's a victory in my book. Congratulations, Justin. Thank you. I just got hit by a pitch.

Brooke and Jeffrey in the morning. We're so done with New Year, New You. This year, it's more you on Bumble. More of you shamelessly sending playlists, especially that one filled with show tunes. More of you finding Gemini's because you know you always like them. More of you dating with intention because you know what you want. And you know what?

We love that for you. Someone else will, too. Be more you this year and find them on Bumble. Jon Stewart is back at The Daily Show, and he's bringing his signature wit and insight straight to your ears with The Daily Show Ears Edition podcast. Dive into Jon's unique take on the biggest topics in politics, entertainment, sports, and more. Joined by the sharp voices of the show's correspondents and contributors. And with extended interviews and exclusive weekly headline roundups, this podcast gives you content you won't find anywhere else. Ready to laugh and stay informed?

Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. People, my people, what's up? This is Questlove. Man, I cannot believe we're already wrapping up another season of Questlove Supreme. Man, we've got some amazing guests lined up to close out the season. But, you know, I don't want any of you guys to miss all the incredible conversations we've had so far. I mean, we talked to A. Marie, Johnny Marr, Eve, Jonathan Schechter, Billy Porter, and so many more.

Look, if you haven't heard these episodes yet hey now's your chance you gotta check them out listen to Questlove Supreme on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts what if you asked two different people the same set of questions? Even if the questions are the same,

our experiences can lead us to drastically different answers. I'm Minnie Driver, and I set out to explore this idea in my podcast, and now, Minnie Questions is returning for another season. We've asked an entirely new set of guests our seven questions, including Jane Lynch, Delaney Rowe, and Cord Jefferson. Listen to mini questions on the iHeartRadio app,

Apple Podcasts, or wherever you get your podcasts. Seven questions, limitless answers. $1.4 billion in NFL quarterback contracts. The untold stories behind the biggest deals in football history. I'm AJ Stephens, Vice President of Client Strategy at Athletes First,

introducing the Athletes First Family Podcast, the quarterback series. My co-host Brian Murphy, Athletes First CEO, and I are sitting down with the agents who have negotiated contracts for Justin Herbert, Deshaun Watson, Dak Prescott, Tua Tugnavailoa, and Jordan Love. Listen to Athletes First Family Podcast on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.