Brooke and Jeffrey: Second Date Update - Second Date Update: Appetizer Energy, Entrée Problems

Episode Date: April 25, 2025

One of our listeners THOUGHT he had a second chance all lined up with his date, but a single one-word text message brought that reality crashing down. Hear what it was coming up in a new Second Date Update!See omnystudio.com/listener for privacy information.

I'm Michael Kassin, founder and CEO of 3C Ventures and your guide on Good Company, the podcast where I sit down with the boldest innovators shaping what's next. In this episode, I'm joined by Anjali Sood, CEO of 2B. We dive into the competitive world of streaming. What others dismiss as niche, we embrace as core. There's so many stories out there and if you can find a way to curate and help the right person discover the right content, the term that we always hear from our audience is that they feel seen.

Listen to Good Company on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hi, I'm Sam Mullins, and I've got a new podcast coming out called Go Boy, the gritty true story of how one man fought his way out of some of the darkest places imaginable. Roger Caron was 16 when first convicted. That spent 24 of those years in jail. But when Roger Caron picked up a pen and paper, he went from an ex-con to a literary darling. From Campside Media and iHeart podcasts, listen to Go Boy on the iHeart radio app,

Apple podcasts, or wherever you get your podcasts. I'm ready to fight. Oh, this is fighting words. Okay, I'll put the hammer back. Hi, I'm George M. Johnson, a bestselling author with the second most banned book in America. Now more than ever, we need to use our voices to fight back. Part of the power of black queer creativity

is the fact that we got us, you know? We are the greatest culture makers in world history. Listen to Fighting Words on the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. My name is Brendan Patrick Hughes, host of Divine Intervention. This is a story about radical nuns in combat boots and wild haired priests trading blows with J. Edgar Hoover

in a hell bent effort to sabotage a war. J. Edgar Hoover was furious. He was out of his mind and he wanted to bring the Catholic left to its knees. Listen to Divine Intervention on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. You Feeling This Too is a horror anthology podcast. It brings different creators to tell 10 vile

Grotesque horrific stories on what scares them the most You're feeling this too Listen on the I heart radio app Apple, or wherever you get your podcasts. All right, it's your second date update podcast with Brooke and Jeffrey in the morning in the home with a second date. And today we have a listener who thought he had the world's most perfect date.

He really did. Until he got a one word text, what, a half an hour after the date was over? Pretty quick after. Yeah, pretty quick. And that's the question, what is your go-to rejection text? Yeah, I just send a vomit emoji

You make me sick, I'll see you tomorrow. What are you Alexis? How do you end a conversation with somebody? Oh, I mean I talk too much. It's definitely not one word It's like a paragraph. I'm like I'm really sorry, but we got his friends. I really enjoyed it, and you're so nice I wish you the best you know long Yeah, exactly Leave it in the comments what yours is and sit back and enjoy the second date today Second date update! You ever have a date with someone where you plan to do one thing together, but then the date night gets closer and suddenly you decide,

Ah, you know what? Forget dinner. Let's do paintball instead. Oh! Wow! That's a right turn. I kinda like it. And then you get a little closer and plans change again. And then your plans change another time. Uh oh. They keep changing. Some people could see that and think,

oh, this person's spontaneous and creative. Oh. ADD like I did. Or just indecisive. Others might see it as chaotic and indecisive. Yeah. Today our listener James isn't sure where he falls cause he says his plans kept changing.

So didn't go out on two dates, didn't go out out on one he calls it one date and a half James welcome to the show hey thank you guys so much man there's a couple indecisive people including myself on this show yeah are you indecisive do you keep changing plans or does this the world keep changing your plans? No, I mean, you know life is life and you know, we like this life Yeah, okay life is coming at you and you had to switch things up right? Yeah I mean cuz after our first date man, texted me and said she had a great time. Oh.

She wants to do it again, right? Okay, wait, wait, who is she? We don't know who she is. Okay, her name is Lisa and absolutely gorgeous. She could be Zoe Zandana's older sister. Ooh. Whoa. That's a compliment.

Yeah, it is. Yeah, it is. Wow. I don't know who that is, but the name is, ooh. The blue girl from Avatar. Oh, I love wow. I don't know who that is but the name is the blue girl from avatar She looks like in that Anything like that then I mean, what's not smurfed, but she's beautiful That's exciting where did you meet her did you say I'm sorry

But we we met on a dating app. Okay, and so yeah, we have same interest and stuff like that I have like my own company. I have to travel a lot and I know with her with her job. She has to travel So okay, that's always nice to find somebody who understands that Right, right, but I mean like for three week, you know, we'll just can we meet here? She's like, oh no my schedule I got a lot of town. Okay, so all right. First week out of town. Then the following week I had to go out of town. So one day I said, well, Hey, well, what about here? Let's meet at this place. She said, well, you know, my girls were going to brunch a day. I said, well, hey, after your brunch, let's just hang out and just have some drinks or something. Oh, poor drinks.

Cause brunch doesn't come without drinks. Yeah, brunch is drinks. The fact that anybody could walk away from a brunch is just impressive in itself. Right, right. And I mean, if we didn't go there, I mean, if it was a nice little place that was next door that we could have had our privacy.

Okay. Well, that's nice too, because like you're trying to accommodate her busy schedule. Yeah. I'm sure she appreciated that. Okay, so how did she respond to that idea? Well, see, that's what I'm gonna say, man. Her response was like, never mind.

I was like, what? Wait, and this is after you'd already gone on one good date. Right, we did on one good date. I was trying to get a half date by going after brunch, but again, I know three weeks had passed, I know things happen and you get back into your routine. So I'm like, yo, at least let me see you or something. You know, let's just drive by each other and wave

like ships in the sea or something. But I'm like, what happened? That is weird. Or maybe she does know, like me and my friends get drinks. I don't want to meet up with you when I'm like three or four Yeah, planning stuff back to back can feel so overwhelming. Yeah, totally. Did she plan anything else with you? No After that, she said never mind and I mean even she couldn't say what could we meet before the brunch? Oh god That's so early

Let's get a grip here Yeah, so before we keep going, let's just rewind back for a second here, James. Can we know a little bit about date number one? Oh, that's a good point. Like, where did you guys go? What was so great about it? Just give us a few details so that we know what it was like. So we went to this Italian restaurant real nice during happy hour and had a great time. Salad, you know, we try to watch those

carbs and stuff, but. You're not a salad, but I'm a great time. Yeah. Salad, had some olives. Right, right. As much, as much dressing as you want. Like, you go back. Yeah. Exactly. I never understand why people who are worried about carbs go to an Italian restaurant. I know, that's all it is.

That's all right. I mean, how's all it is. That's alright. I mean, how was the conversation, the connection between you two? Yeah, I mean, it was good. We had a great conversation. We found out we liked certain things, you know, our spirit animal. I don't want to go into too much detail, but... Okay. Hey, I forgot to say, we did have a kiss.

Oh, you did? Okay. There was a kiss, right? You know, at the end of the day, nothing elaborate, but just nice But just nice kisses like cool and then I get this text. She enjoyed it She had a great time and she said let's do this again So there was like no doubt in your mind that this was going somewhere What exactly? Yeah, I think like the scheduling thing I understood But I don't I don't understand like why this was like never mind

So there hasn't been there's never like, never mind. That's weird. And so there hasn't been, there's never been a second meetup that's materialized out of all this. Correct. I would like for it, but nah. Wait, why'd we say there was one and a half then? There was only one.

Well, he was trying for the half, I guess. The brunch. Yeah, she- It didn't happen. Yeah, it didn't happen. Well, it did happen with her and her girlfriends. He just wasn't there. Oh, that doesn't count for me. Yeah, it doesn't. In, it did happen with her and her girlfriends. He just wasn't there.

That doesn't count for me. Yeah, it doesn't. In a guy's world, that counts. In a desperate man's world. Well, that's where we're at with James. That is terrible. I went on four dates last week. They all said no.

But in my mind, we were partying. So James, we're going to reach out to Lisa for you. We'll see if she picks up, and then we'll try and get you your second date update right after this. Hold on. I think. Second date update. If you're just joining us for the second date update, our listener James has spent the last

three weeks arranging and rearranging plans, desperately trying to meet up with a woman named Lisa, who he already went out with once and... Yeah. ...Brooks yawning about the It was a great first date it was it was yes according to her I'll be out on that stuff. Nobody would know I'm just looking around the room According to James and to Lisa because she responded afterwards that it was great.

They had a good kiss, a top notch Caesar salad, everything you could ever want in a romantic first meetup. No croutons though. Gotta watch those carbs. And now, after all that effort, the last thing that Lisa texted him was, never mind. It's one of the top three worst things a woman can send to a guy. But James, we're going to try and help you get this thing back on track. James Bond All right, sounds great. Yeah? Oh, yeah. Oh, you're done for. Nobody texts with it like that. It's like end of conversation. That definitely was it. Never mind.

Yeah. That was bad. Well, now I don't even know if she'll pick up, but Seriously. Let's see if she answers. I'm gonna dial her number right now. Hopefully we can get some answers out of her. But here we go. Hello. Hey, is this Lisa?

Max is calling. Yeah, we're a radio show called Brooke and Jeffrey in the morning. Hi Lisa, the whole show's here. Hey, good morning. Hi, um, my ex, why are you calling me? Yeah, we're doing this segment. It's called Second Date Update where we try to help out listeners who've gone out with somebody and they're having trouble arranging that second meetup. We try and help facilitate it or figure out if there's a reason why the other person doesn't want to see them again. Yeah. And you can't say never mind.

You have to participate. Okay. And you can't say never mind. You have to participate. Okay. And you're calling me why? Because a little while ago, almost a month ago, you went out with one of our listeners named James. Was it that long ago? He said three weeks ago. Okay. With a guy named James?

Mmm. Yeah, I'm not in contact with him. Yeah, he understands that. Yeah, we got that vibe. It sounds like it things shifted though did it shift for you because at first he thought you were liking him Yeah, I guess I mean the thing that's confusing to him is that after that first date He said you guys even texted each other about having a great time And you said you really wanted to meet up again, or were you just pulling like Alexis would and just trying to be nice? Yeah. Yeah. You know, I mean, honestly, it's funny, but it's true.

I wouldn't have said it if I didn't mean it, but that was then. OK, so something has changed. Yeah. What happened? Well, OK, so like I text him and I did tell him that I had a wonderful time and we were trying to meet up to see each other. OK. And so at that point, you're excited about him, right? Yeah, I mean, absolutely. But it went from let me buy you dinner and then it went to let's get drinks.

Then let me buy you drinks after brunch with my friends. And I'm the type of woman where if a guy says he wants to buy me dinner, then I'm gonna hold him to that. And however, with James, our potential meetups became progressively worse. So you felt like as the conversation went on, he was willing to put less effort into meeting up with you.

Listen, when a man says that he wants to buy you dinner, then I expect him to buy me dinner and not say, okay, let me buy you dinner. Then the next thing is like, okay, you know what? You know what? Let me get you drinks. You know what? You know what?

Let's just meet up after you hang out with your friends and we'll just spend a little 10 minutes. Okay. So it didn't make you feel special, but did you have time to get dinner? I thought you didn't have time. Well, there were times that I didn't have time and there were times where he didn't have time But you make time. Okay, we're in it out and you make time. It's just not a drive-by

Oh, let me just see you real quick and keep going like I don't even know you like that It's like I think he took it as he was putting in extra effort to try to make Yeah, like shift around you and I know that you know making time is very important. He's made time to be on the phone with you right now listening on the other line waiting to talk to you. Talk about effort. You didn't tell me that you were going to be on the phone. Yeah we did just now. I think this is a misunderstanding honestly. James talk to her.

I think this is a misunderstanding honestly James talk to her Well, yeah, I mean Lisa. I'm not treating you as a drive-by I was trying to make time so I can at least see you and so we can have Conversation but that was the whole purpose of doing it so you can get to know me James You text me let me buy you dinner and having drinks after being with my girls is not buying me dinner Well, I didn't realize I had to be a bread basket in order to hang out with you. Oh I don't even know what that means either. I don't know you mean you go to a dinner They usually give you bread before you have your dinner. Okay, you had to feed a meal to her That's exactly what she's saying because if I'm giving effort to meet you and you said you want to get dinner with this

It's two people at the same time, you know Dinner after the brunch you could have said said we went to go to dinner after brunch. That'd be really a late brunch. I can eat that much. I mean, I get her. Like, not directly after, but later on that same day. Clearly, I had time to go to brunch, then maybe later on that evening, I would have had time for dinner.

But you didn't think about that. Oh. You could have said it, maybe. No, neither did you think about that. And I didn't know your love language was food like that. How about that? I didn't know your love language was food. My love language is time and consideration and you don't think about it. But there's no time and consideration. You guys are fighting over that. Everybody needs to just relax just a little bit because this just sounds like a big communication misunderstanding We're forgetting that they had a great first date. They both admitted it That's true that the conversation was great and the chemistry was on and the only problem that has come up is Communicating how and when to meet up the second time so James

I mean that would be like do not want to meet her for dinner like isn't dinner point, I'd rather just send her door dash and she can have a full course of meal. Hey girls love that. I think she just wants the energy, not someone to pay for her dinner. She just wants the thoughtfulness is what it sounds like. Exactly. Lisa, this was thoughtful. When we first talked to James, he described you as Zoe Saldana's younger hotter sister no I actually said the older hottest I'm trying to protect you here James oh maybe

just go with what I said he called me the older but hotter I mean how about this how about this? How about this? Think of this, Lisa. He went out of his way to get a radio station to call you because he wanted to see you that much. That is effort. It sounds like he had you call me to embarrass me. No.

It doesn't sound like he was trying to flatter me. No, it's the opposite. He wants to go out and actually spend time at a dinner with you, a dinner that we would pay for if you'll agree to meet up with him again Delete the last three weeks from your mind and just remember after that first date how good you felt about each other Yeah, I don't know now because I feel like he's gonna like he might stand me up. What? Why would he stand you? Okay, no, no, no, no. She's creating stuff

now. Now she's going from a happy hour to a hostile hour, which is going to probably lead to a hostile dinner. Oh, God. Okay. That was good branding though. Hostile hour. Oh, man. Okay. So wait, does that mean that you're not interested in a date? Not anymore. Wait, she said yes and he said no? No, I think they both said no. What did I hear? Yeah, I'm not interested in going out with that windbag. Oh, okay. That wasn't no then, never mind. Okay. That's okay, the feeling is mutual. Oh, wow. Okay, well, this one didn't work out. Those vibes, they shifted, those vibes shifted. Yeah, and James's words, life is in James's words life is life

Right now am I right James yeah, the thrill is gone They really are Jeffrey in the morning, you know by the end of that call I don't know if there was anything that we could have said to save that situation Yeah If there was anything that we could have said to save that situation They kind of took over yeah Clashing I think dating is hard for both of them right now, and they just took it out on each other Mean like it's just like I hate it all they're both too busy and sleep-deprived, baby Right but on a positive note James did give us three of our top quotes for the entire year.

Happy hour turned into hostile hour. Life keeps on lifin'. And you want a breadbasket with that wine? That was a whole school. I kind of workshopped it. I changed it a little bit. Sounds like a threat now. You want a breadbasket with that bit. I always want a breadbasket. So my response is always going to be yes. The whole thing was promises made, promises not kept. Good

news is we don't make any promises when you go listen to us on podcast at Brooke and Jeffrey. Just life is life. And on that's how we. Go check it out online, wherever you get your podcasts, at Brooke and Jeffrey. Brooke and Jeffrey in the morning. I'm ready to fight. Oh, this is fighting words. Okay. I'll put the hammer back. Hi, I'm George M. Johnson, a bestselling author with the second most banned book in

America. Now more than ever, we need to use our voices to fight back. Part of the power of black queer creativity is the fact that we got us, you know? We are the greatest culture makers in world history. Listen to Fighting Words on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hi, I'm Sam Mullins, and I've got a new podcast coming out called Go Boy, the gritty

true story of how one man fought his way out of some of the darkest places imaginable. Roger Caron was 16 when first convicted. He spent 24 of those years in jail. But when Roger Caron picked up a pen and paper, he went from an ex-con to a literary darling. From Campside Media and iHeart podcasts, listen to Go Boy on the iHeart radio app, Apple podcasts, or wherever you get your podcasts. My name is Brendan Patrick Hughes,

host of Divine Intervention. This is a story about radical nuns in combat boots and wild haired priests trading blows with J. Edgar Hoover in a hell bent effort to sabotage a war. J. Edgar Hoover in a hell-bent effort to sabotage a war. J. Edgar Hoover was furious. He was out of his mind, and he wanted to bring the Catholic left to its knees. Listen to Divine Intervention on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I'm Michael Kassin, founder and CEO of 3C Ventures and your guide on Good Company, the podcast where I sit down with the boldest innovators shaping what's next.

In this episode, I'm joined by Anjali Sood, CEO of Tubi. We dive into the competitive world of streaming. What others dismiss as niche, we embrace as core. There are so many stories out there. And if you can find a way to curate and help the right person discover the right content, the term that we always hear from our audience is that they feel seen. Listen to Good Company on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

You Feeling This Too is a horror anthology podcast. It brings different creators to tell 10 vile, grotesque, horrific stories on what scares them the most. I'm crying! You're so funny! You're feeling this too. Listen on the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts.