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I'm here on the job site with Dale, who's a framing contractor. Hey, good morning. Dale traded up to Geico Commercial Auto Insurance for all his business vehicles. We're here where he needs us most. Yep, they sure are. We make it easy for him to save on all his insurance needs, all in one place with coverage that fits his business and bottom line. Oh, I shouldn't have looked down. It's all right. We're so far up here. Look at me. Take a deep breath. I'm good. So good. Get a commercial auto insurance quote today@geico.com and see how much you could save. Get more with Geico. The Super Secret Bestie Club Podcast Season 4 is here and we're locked in. That means more juicy cheesement, terrible love advice, evil spells to cast on your ex. No, no, we're not doing that this season. Oh, well, this season we're leveling up. Each episode will feature a special bestie, and you're not gonna wanna miss it. My name is Curly. And I'm Maya. Get in here. Listen to the Super Secret Bestie Club on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Let's start with a quick puzzle. The answer is Ken Jennings appearance on the puzzler with A.J. jacobs. The question is, what is the most entertaining listening experience in podcast land? Jeopardy truthers believe in? I guess they would be conspiracy theorists. That's right. They gave you the answers and you still blew it. The Puzzler. Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your PO. So what happened at Chappaquiddick? Well, it really depends on who you talk to. There are many versions of what happened in 1969 when a young Ted Kennedy drove a car into a pond and left a woman behind to drown. Chappaquiddick is a story of a tragic death and how the Kennedy machine took control. Every week we go behind the headlines and beyond the drama of America's royal family. Listen to United States of Kennedy on the iHeartRadio app, Apple Podcasts, or wherever you get your podcast. Foreign Business Month and Money and wealth podcast with John Hope Bryant is tapping in. I'm breaking down how to build wealth, create opportunities, and move from surviving to thriving. It's time to talk about ownership, equity, and everything in between. Black and brown communities have historically been last in line. Let me just say this AI is moving faster than civil rights legislation ever did. Listen to Money and wealth from the Black Effect podcast network on iHeartRadio app, Apple Podcasts or wherever you get your podcasts. Happy Monday. It is your second date podcast. Thanks so much for being here. It's Brooke and Jeffrey in the morning, and I would love in the comments today for people to share the awkward ways their day ended. You know, not all are just a simple kiss or a little hug. No, some of them get weird, and that definitely happens in today's second date update. Yep. So let us know, because, you know, we love reading your comments. What do you see, Alexis? Yes, Sivanesh said. Hey, guys. Listening all the way from Malaysia. Oh, cool. I discovered the show through a second date update clip on TikTok, and I've been hooked ever since. I started with the second date playlist, then I moved on to awkward Tuesdays and masked speakers, and now I'm all in on the full show. Wait till you hear the phone tab. Yeah, yeah, right? I mean, hey, you do get a full hour if you somehow want more of this. Remember, we have a second podcast feed that is just Brooke and Jeffrey. Yes, it's the same goofy pictures of us in the. Yeah, in the. In the pod. But you'll find it and you can get even more. All right, we're gonna start your second date right now. Second date update. I'm not sure if you guys remember this, but about six months ago, we did an awkward Tuesday phone call with a listener named Kevin. Okay. Who wanted to ask out his co worker, and he was super nervous about it, needed our advice. The call wasn't perfect. Yeah, he had some stumbles along the way, but she doesn't sound like our show Jeff every call that we do. Yeah, Absolutely flawless. Remember what happened in the end? She did say yes and agree to a date with him. But wasn't it kind of like. I guess. I don't know. It was a yes. Okay. Now, apparently they went out a few times, things fizzled, didn't quite last. So Kevin has jumped back into the beautiful oasis we call the modern dating pool. Oh, man. And again, that was months ago. So, Kevin, how's it been? Have you had a lot of dates in that time? Like 10. 10. 10 days? Dude, you're doing dates in the last two years. You're doing some work. Congratulations. You're a catch. Yeah, but I actually haven't had a second date. Oh. Oh. But is that from your choosing? Like, maybe you didn't want to go out again with any of them? No, I would have been happy to go out with really any of them again. Oh, okay. Okay. That's hard. Yeah. Yeah, that hurts. Set them up for that? Brooke, you're here. We're going to help you. Yeah, they haven't been the greatest. I actually had a really bad one. Yeah, she was a nice girl, I thought. But when I walked her out to her car, I opened the door and then she just sucker punched me and then drove off. What? Wait, what did you say? She punched you? I'm so sorry to laugh. I did not expect that sentence. That is terrible. Did she punch you in the face? It's actually in the back of my head. I was opening her door and then all of a sudden I just felt this like. Did you ask permission to open the door for her? Because she may really have not liked that. You weren't fast enough for her. Maybe so. I don't know if she thought I was going to kiss her or. Your head was. How are you gonna kiss her when you. Yeah, maybe she thought that you were trying to steal her car so she had to stop you. It has to be a self defense move, right? He's not like, hey, give me the keys. I don't know. Was it that bad? I don't know. Some people give off natural Grand Theft Auto vibes, so maybe you fell into that category. Just ask. Are you okay? Now I am. Yeah. Okay. Confused. Still concussed. So is sucker punch girl the one you want us to call for a second date update? No, bro, I kind of want to talk to her. We'll call her a Brook fighter. Well, who do you want to call? I've had this really bad luck until I met Chelsea. Chelsea. Chelsea. Okay. It's a new girl. Hey. Okay. No physical violence, I hope. Yeah. Tell us about your. I'm assuming you went on a date with Chelse. Yeah, she didn't punch me. That's all I wanted to know. Actually, we're improving. I thought it was a good sign. And we connected the best out of all of the first dates I went on. Okay, what made it the best? I just felt like I could talk to her because, like, when we went on our coffee date, it was a good conversation, even though it didn't last very long. Okay. It was actually only like 20 minutes. Why was it so short? You know, I'm not really sure. My friend stopped by and. Your friend? Yeah, I don't really know why. Okay, so you had a friend come by randomly and you talk to the friend a little bit and you feel like maybe she got offended that the attention was taken away from her. I may. I don't know. I. That would be weird to me. She Got a friend in. If you're only there for 20 minutes and you have a five minute conversation with a friend, that's one fourth of the date. Especially they're trying to play it off. Hey, Brooke. Good to see you here. Yeah. Aren't you successful and beautiful? I feel like I normally wouldn't ask this, but I feel like I need to know. Chelsea, she's not the barista, right? You're not considering that a date? That's creative. Like, she doesn't work there? No, she doesn't work there. Okay, That's a good question. So how did it end? Yeah. After the 20 minutes, how did you two leave it? She said she had to do something, so we got up and left. And I guess that was kind of weird too, because I was kind of like behind her for a couple of blocks while she. Wait, What? That's like the most awkward thing ever. And then she started to jog. And then you started to jog. You're like, hey, I'm gonna run after you in case someone weird chases you. I end up. I lost her. Oh, I lost. She lost you, I think. Yeah. Yeah, that's the real way. Did she know you were back there? I don't think so. I don't know. Okay, but you weren't following her. That was just a coincidence that we had the same route home. Dude, I hate that. Even when that happens with my friends. Yeah. And we say goodbye at the restaurant and then we're like, yeah, okay, I should have done this later. You get it. All right. So how long has it been since this 20 minute date? Like, right at. Two weeks. Two weeks. Okay. Oh, that's not good. And have you reached out much with her? I. I was texting her quite a bit, yeah. Oh, we may have overset it. Yeah, we might. We may find out if you've crossed any lines or how many texts you've actually sent when we call her here. I think it's more how far he did cross the line. Yeah. Or maybe they're right in that sweet spot. We don't know. Brooke, remember when you said you had hope? Yeah, I do have hope. As long as you didn't send her a picture of the back of her head as she was walking away from you on the sidewalk. He was just trying to make sure she doesn't get sucker punched back there like he did. I was gonna say when I was on last time, Brooke, you told me to be, you know, more assertive, so I'm really trying to be here. Oh, boy. Now he's so assertive. He follows ladies in their car. There's a balance that we need to discuss. The good thing is, though, you're maybe figure it out. You weren't trying to be weird. You were just trying to walk to your car. And maybe that's not why she's not calling you back at all. We're making stuff. Ok, well, let's call her and use that assertion to aggressively get you a second date. We call Chelsea right after this. Hold on. Second date update. Don't you hate it when you're on a first date and the girl says she has to go and you accidentally follow her all the way home? I think it was only three blocks, to be fair. I mean, enough blocks to be alarming. But he lost her. That's what happened to our listener Kevin. Sort of. He wasn't following his date Chelsea on purpose. They just left the coffee shop at the same time. And he coincidentally was walking behind her on the street for a long, long while. I mean, at any point did you think I should take a different route or just stop for a second? Yeah, stop. Hopefully he didn't think. Speed up. Yeah, let me catch up with her. Did that thought come to your mind at all, Kevin? Any of those? Yeah, well, I didn't think it was that weird. And so I've been thinking about it, like, while we were on hold, and I think you should tell her that I didn't intentionally walk behind her because I really did it. Okay, so you want. You want us to let her know that? Okay. Yeah. Okay. Okay. We're not exactly sure what happened there. We just know that the date was only 20 minutes long, which is kind of short to get to know someone. That's honestly the bigger concern for me. Like, why did she only stay for 20 minutes? The following is a totally different story. If you were in a hurry, why would you even schedule a date during that time? Maybe she's just trying to squeeze it in. It's like one of those pre dates where it's just like a quick coffee. Like, will this be worth a full night? You didn't catfish her with, like, a photo of Liam Hemsworth, did you? Because you do sound like a Liam to me right now. Kind of hunky. I'm actually blushing right now. But no, Kevin Hemsworth does not have a name. Could have fooled me. But let's call Chelsea here. We'll see if we can get an explanation from her if she picks up. All right, here we go. Hello? Hey, is this Chelsea? This is who's calling this is a radio show calling called Brooke and Jeffrey in the Morning. Hey, Chelsea. What? What? What? Is this fun? For some of us, it's fun. It's a segment we do call the Second Date Update. And we're looking to. Sorry. Okay. She's just listening. Okay. She's actively listening by interrupting me. But it's okay. We're trying to help out one of our listeners that you went out on a date with recently. He says he had a really good time with you, but it ended kind of short. His name is Kevin. Okay. I'm hoping that was a smile and not a laugh. Yeah, sensitive reaction. We're calling because Kevin told us a little bit about your guys date. Coffee Day. Coffee Day. And it. From what we heard, it sounded pretty fun. Tame, Short. That was two weeks ago. Yeah. Yeah. But he really said he liked you. He thought you were awesome. He wanted to see you again. He said he's been pursuing it, actually, and texting you, trying to organize something, but he doesn't understand why nothing's happening. Yeah, he has sent me quite a few texts, but I guess I'm confused as to why he doesn't understand why things start moving forward. Did you write him back? He. I mean, I guess we never asked if you ever texted him back. Or is it like, that obvious? From my perspective, it was pretty obvious. Okay. The only. The only idea that he had about the date, about why it would have ended so quickly, is he did mention one of his friends stopped by and said hi. That's what he said. He. He said a friend stopped by. Yeah. Yeah. Really quick, or you think that they weren't actually friends? Was it an enemy? Was it his ex? No. I mean, as far as I know, I don't think it was an ex, but I don't know. 30 seconds a minute into us meeting at the coffee shop, this guy comes over and sits like, right next to us, isn't looking at me at all. So I asked Kevin, I was like, hi, can we introduce him? He's like, well, no, no, no, don't. He's not engaged in the conversation. He's just my emotional support friend. Oh, emotional support friend. That's kind of funny. So originally I thought he might have been kidding. And so I laugh and he's like, it's not funny. This is Charles. I've had a couple of poor dates, and Charles is really there to just kind of help me with my confidence and communicate more effectively. Wasn't that kind of endearing to you? Like, he wants to make sure that goes Well, I mean, I think if maybe I had been given a heads up, I would have been more open to the idea. That's fair. Yellow vest that threw you off. Emotional support friend vest. Dude, that's amazing that he can find a friend that will take the time to go on a date with him. I mean, that'd be. But I'll say. I think that that says a lot about Kevin, that he must be a good friend. I need to know, is Charles sitting on his phone? Is he just listening, taking notes? What's Charles doing? We got the impression that he just popped in right. Real quick and left. No, not at all. He was there the whole time. He wasn't really engaging in the conversation. He was just there. Did he hype Kevin up ever? You know, like. He's not a hype man, Brooke. Well, I just didn't know. How do you support. I mean, he laughed at some of the things that Kevin said, but beyond that, there. There wasn't much interaction. Everybody needs a good backup laugh friend. Charles needs to move a few tables over. Yeah, we didn't know that was how it played out. We got a little bit of a different version of that story. I wonder if Charles is on the phone, too. Yeah, because, oh, my gosh, we have an emotional support friend quietly listening on the other line right now just to make sure that I do a good job with this segment. And that person is Kevin. Yeah, Kevin's here. What? He's on the phone? Yeah, he's really. Actually, he wants to talk in this conversation, so I'm going to give him permission to jump in and say something. Okay. I don't know if he's there. Kevin, you there? Yeah, I'm here. How you doing, buddy? Hey. I'm good. I'm just. I'm listening. Yeah, I. I don't understand what the big deal is, really. Kevin, when did you get an emotional support bro? You didn't tell us about that. Well, yeah, I mean, a friend is a friend. He doesn't need, like, a title or anything. Sounds like you gave him a title. You. You called him your emotional support friend. Yeah. And Kevin, you brought him along on the. And didn't tell us the whole time. I mean, yes, he was there, but he was there for me. Sure, sure. But, Chelsea, do you. Do you see where he's coming from? I guess. I mean, but you kind of have to put my. Like yourself in my shoes, Kevin. It's. It's a little bizarre to just have a third person there without kind of giving the heads up. Why and not engaging, really in the conversation. Yeah. Are you mad because he didn't laugh at your jokes and he just laughed at. I'd be mad. That's a good question, guys. Chelsea? No, not really. I don't think I was particularly funny because I. I was kind of creeped out by the whole thing. She's like, I told so many jokes and just. Kevin, do you think that maybe you could have told her prior to the date that he was coming along? Yeah, he's gonna be around. I didn't need to tell her because he wasn't gonna do anything. Like, he's just like wallpaper. He's gonna be there, you know, for me. So what I think, Kevin, Chelsea is saying that it's hard for her to connect romantically with you. I don't even mean romantically. I just mean as a person to person. It's hard. Yeah. Kevin. It's a little bit dist. Kevin. Maybe he's waiting for Charles to respond. Wait, is Charles here? Charles, speak up right now. Okay, so it's a little bit distracting, I guess. But, like, the thing is, I can tell him to do whatever I want. Does that make sense? Because I'm the one that's paying him. You're paying? Oh, you pay. He's paying him. He's paying him kindness. It was hard. I mean, okay, yeah, he was technically not facing you for the time, but, I mean, I could. Guess I could get him to, like, face the wall if you really wanted. Kevin. Well, I do think that would be better. That's. That's at least a good first step. Can we agree on that? Awkward. Kevin. I mean, we're going to tell him we left now. Just there. The rest of the day. Put a blindfold in a ball gag. He can't see, he can't speak, can barely lie. Both of you. Emotional support is totally normal and needed, but let's get you a dog. Or, you know. Yeah, but dogs can't laugh at jokes. Exactly. And it was a good day. It wasn't. Did you hear that? It wasn't a good date. I am so sorry, you all. I don't understand why this was even a conversation. It was awkward and weird, and I've got to go. I hope you all have a great day. Okay? Thank you. Sounds like you need an emotional support friend to deal with that. Don't. Don't. That was a little. She keeps having to go, and I think that's rude. Yeah, Kevin, she's not interested. And I don't know that you're gonna find many that are interested when Charles has to be there with you. But a dog? A lot of women would be interested. Yeah, emotional support for animals are kind of weird. I prefer people. Okay, maybe get. Maybe just follow her home again and see if she changes her mind. Jeff stops Brooke and Jeffrey in the morning. Welcome to Pretty Private with ebony, the podcast where silence is broken and stories are set free. I'm Ebony and every Tuesday I'll be sharing all new anonymous stories that would challenge your perceptions and give you new insight on the people around you. On Pretty Private, we'll explore the untold experiences of women of color who faced it all. Childhood trauma, addiction, abuse, incarceration, grief, mental health struggles and more. And found the strength to make it to the other side. My dad was shot and killed in his house. Yes, he was a drug dealer. Yes, he was a confidential informant, but he wasn't shot on a street corner. He wasn't shot in the middle of a drug deal. He was shot in his house, unarmed. Pretty Private isn't just a podcast. It's your personal guide for turning storylines into into lifelines. Every Tuesday, make sure you listen to Pretty Private from the Black Effect Podcast network. Tune in on the iHeartRadio app, Apple Podcasts, or wherever you listen to your favorite shows. What would you do if one bad decision forced you to choose between a maximum security prison or the most brutal boot camp designed to be hell on earth? Unfortunately for Mark Lombardo, this was the choice he faced. He said, you are a number, a New York state number, and we own you. Shock incarceration, also known as boot camps, are short term, highly regimented correctional programs that mimic military basic training. These programs aim to provide a shock of prison life, emphasizing strict discipline, physical training, hard labor and rehabilitation programs. Mark had 1:1 chance to complete this program and had no idea of the hell awaiting him the next six months. The first night was overwhelming and you don't know who's next to you and we didn't know what to expect in the morning. Nobody tells you anything. Listen to Shock incarceration on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Man, I don't say this about many people, but this show is an open door for Kevin whenever he wants to come back. He is officially a friend of the show, even if he wasn't being one truthful with us about his emotional support friend. I like him and I would let him follow me home anytime. Is he the only one that pushes back on dogs? That people are better than dogs? They're not, Kevin. People are your problem. Yeah, everybody agrees. All the people on the text board are saying dogs are better than people. Yes. Yeah. Get the right emotional support animal. Actually, wait, did his emotional support friend follow Chelsea home, too? Hey, I didn't think of that. So there was two dudes following it. If there's two guys following you now, I kind of understand the creepiness. Especially when he's talking to his friend and going, what is it, boy? You didn't understand the creepiness when the guy was sitting next to him staring at her. The date itself was pretty awesome. Yeah, I mean, he's just being supportive. Very closely supportive. Oh, well, there's better ways. Yeah, well, there's better ways. You should have done a FaceTime. Totally. Yeah. I mean, he honestly could have had her him on speakerphone and just set the phone on the table. Maybe you. There's lots of life lessons to be taken from these segments and you can go find them online wherever. You get your podcast at Brooke and Jeffrey and then email the show. We can call that person who isn't calling you back. Brooke and Jeffrey in the morning. Let's start with a quick puzzle. The answer is Ken Jennings appearance on the puzzler with A.J. jacobs. The question is, what is the most entertaining listening experience in podcast land? Jeopardy truthers believe in? I guess they would be conspiracy theorists. That's right. They give you the answers and you still blew it. The puzzler listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Everyone thinks they'd never join a cult, but it happens all the time to people just like you and people just like us. I'm Lola Blanche. And I'm Megan Elizabeth. We're the hosts of Trust Me, a podcast about cults, manipulation and the psychology of belief. Each week we talk to fellow survivors, former believers and experts to understand why people get pulled in and how they get out. Trust me. New episodes every Wednesday on. Exactly right. Listen, wherever you get your podcasts, what would you do if one bad decision forced you to choose between a maximum security prison or the most brutal boot camp designed to be hell on earth? Unfortunately for Mark Lombardo, this was the choice he faced. He said, you are a number, a New York state number, and we own you. Listen to shock incarceration on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. So what happened at Chappaquiddick? Well, it really depends on who you talk to. There are many versions of what happened in 1969 when a young Ted Kennedy drove a car into a pond and left a woman behind to drown. Chappaquiddick is a story of a tragic death and how the Kennedy machine took control. Every week we go behind the headlines and beyond the drama of America's royal family. Listen to United States of Kennedy on the iHeartRadio app, Apple Podcasts, or wherever you get your podcast. It's Black Business Month and Money and wealth podcast with John Hope Bryant is tapping in. I'm breaking down how to build wealth, create opportun opportunities, and move from surviving to thriving. It's time to talk about ownership, equity, and everything in between. Black and brown communities have historically been last in line. Let me just say this AI is moving faster than civil rights legislation ever did. Listen to Money and Wealth from the Black Effect podcast network on iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Episode Title: Two’s Company, Three’s An Intervention
Release Date: August 18, 2025
Podcast Host: iHeartPodcasts
In this classic “Second Date Update,” Brooke, Jeffrey, and their team help listener Kevin solve the mystery of why he’s being ghosted after a coffee date with a woman named Chelsea. What starts as a typical awkward first date story quickly spirals into an unexpected intervention about friendship, boundaries, and the true meaning of “emotional support.” The episode is packed with the show’s trademark humor, gentle roasting, and genuine curiosity as the team unravels an especially bizarre situation: Kevin has been bringing a paid “emotional support friend” along on his dates—without notifying his dates.
Kevin on being ghosted:
“I actually haven’t had a second date … No, I would have been happy to go out with really any of them again.” (10:05)
Brooke on support animals:
“Emotional support is totally normal and needed, but let’s get you a dog.” (29:15)
Chelsea’s reaction to Charles:
“It’s a little bizarre to just have a third person there without a heads up.” (28:30)
Jeffrey’s Summation:
“He is officially a friend of the show—even if he wasn’t being one truthful with us about his emotional support friend.” (Outro commentary)
Lighthearted, self-deprecating, and gently irreverent. The panel mocks Kevin’s situations with compassion (and genuine disbelief), while Chelsea’s candor keeps the segment grounded. Kevin’s earnestness is endearing if naive, and the hosts ultimately root for him—just not his chosen method.
This outlandish Second Date Update is a prime example of why the segment boasts a “low success rate…high entertainment for the rest of us.”