Brooke and Jeffrey: Second Date Update - Second Date Update: Randall Is Back For More

Episode Date: July 18, 2025

After many failed romantic encounters...and a couple of outright scams...one of our most lovable listeners is back! He says this time is different because he finally executed the perfect date night, at least for a few minutes. We'll find out what went wrong this time in your brand new 2nd Date Update!See omnystudio.com/listener for privacy information.

The Girlfriends is back with a new season, and this time I'm telling you the story of Kelly Harnett. Kelly spent over a decade in prison for a murder she says she didn't commit. As she fought for her freedom, she taught herself the law. He goes, oh God, Harnett, jailhouse lawyer. And became a beacon of hope for the women locked up alongside her. You're supposed to have faith in God, but I had nothing but faith in her. I think I was put here to save souls by getting people out of prison. The Girlfriends, Jailhouse Lawyer.

Listen on the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Join iHeart Radio and Sarah Spayne in celebrating the one-year anniversary of iHeart Women's Sports. With powerful interviews and insider analysis, our shows have connected fans with the heart of women's sports. In just one year, the network has launched 15 shows and built a community united by passion. Podcasts that amplify the voices of women in sports.

Thank you for supporting iHeart Women's Sports and our founding sponsors, Elf Beauty, Capital One, and Novartis. Just open the free iHeart app and search iHeart Women's Sports to listen now. I'm Bob Crawford, host of American History Hotline, a different type of podcast. You, the listener, ask the questions. Did George Washington really cut down a cherry tree?

Were JFK and Marilyn Monroe having an affair? And I find the answers. I'm so glad you asked me this question. This is such a ridiculous story. You can listen to American History Hotline on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. I knew I wanted to obey and submit, but I didn't fully grasp for the rest of my life what that meant. For My Heart podcasts and Rococo Punch, this is The Turning, River Road. In the woods of

Minnesota, a cult leader married himself to 10 girls and forced them into a secret life of abuse. But in 2014, the youngest escaped. Listen to The Turning, River Road on theHeartRadio app, Apple podcasts, or wherever you get your podcasts. My Uncle Chris was a real character, a garbage truck driver from South Carolina who is now buried in Panama City alongside the founding families of Panama. He also happens to be responsible for the craziest night of my life. Wild stories about adventure, romance, crime, history, and war intertwine as I share the tall tales and hard truths that have helped me understand Uncle Chris.

Listen now to Uncle Chris on Will Ferrell's Big Money Players Network on the iHeartRadio app, Apple Podcasts, or wherever you listen to podcasts. Welcome to your brand new second date update on a Friday even. Yay! The best day! Makes it a little better. Hey, it's Brooke and Jeffrey in the morning and we have one of the most lovable, one of our favorite listeners back for a second date. Lovable and most gullible.

Yeah, yeah. He has fallen for some romantic scams in the past, but he says this time is different and we're going to find out why here in a second. He's entertaining, that's for sure. But earlier this week, we asked you to comment the most embarrassing thing your parent has ever posted. And we can't let those answers slide by. No, I saw them and I had to read them. Alright, two I saw that I liked is one person, Preslyn, said,

My mom posted a video of me singing every word of satisfied from Hamilton. Oh God. Oh! And then, will you ever be satisfied? Oh, man. I need to know how old you were, too. I have questions. I feel like the older, the more embarrassing it is.

Yeah, exactly. Hopefully you were little. And another one from Freethinker said, the most embarrassing thing my family posted, my mom wrote what was meant to be a personal message as a post, and it was all about her bowel movement. Oh! Complaining about my dad and asking me questions about symptoms from when I was sick with the stomach virus

Personal stuff I didn't see it until two days later So it was fun to see the comments and beg my mom to delete it. Oh my gosh Right my son I hit post Oh my gosh I'm just gonna write my son, I hit post Everyone's like, you're eating and she's like, I don't know how She's like, I started a group message That is so funny Oh, those are so good

Hey, thanks for being here and being part of this weird brick and jeffery family We're starting a brand new second date update right now Second date update I'm gonna do a quick recap about one of my most favorite listeners. We've had on the show in the past year And I'm gonna do it cuz he's back today His name is Randall and last time we spoke to Randall he had met not one but two international women on the internet. One was from Vietnam, the other from the Philippines,

and he had even flown out to meet the first one in Vietnam. Yeah, they turned up not at the airport. Yeah, she never showed up to their date. We didn't call that woman, we ended up calling a different lady, someone that he'd met locally, because his friend had suggested, Why not try dating in your own area code? Great friend. Why try not getting scammed? Yeah, and that woman ended up just wanting to be his friend.

And help him avoid scammers. But the thing that we learned about Randall is that he believes in the power of true love. That's true. Yep. And he's just had a bad run of luck lately and needs our help. So I'm curious to hear about his latest romantic endeavor. Randall, my guy, welcome back to the show. How you been?

Man, thank you guys so much for having me back on. I really appreciate you. Can you tell me in the time between the last time we talked and now you have wired no one money No We're learning we're growing that's great, but what brings you back today Well, I had a few friends listen to the show the last time and they agreed with you guys that I should try dating more locally first. And surprisingly I started doing that, but it hasn't gone that great to be honest guys.

Are you on the apps? Is that how you're finding women locally to date? Well, I met a girl named Sammy and we met in person. Oh, better. You are doing a good thing where you're looking at the past mistakes and learning and adjusting and adapting. That's all very good.

Yeah. Now you guys know me. I'm a romantic. Right. So I surprised her with a very special date. I'm scared. I took her on a picnic to an outdoor movie. Cute.

That's great. Well, you can't really talk, can you, during the movie? It doesn't matter. It's cute. And it's outdoors. People are only halfway through. Okay halfway through. How did it go? Well, I think the first 30 to 45 seconds was good. What? Seconds? Well, that's a good start. Yeah. Just my luck. Right after we sit down, we get situated, she goes, Oh my gosh, I think my friend's here. Then she looks at me and

says, Do you mind if I text them where we are? So of course you were like, yeah, tell your friends to come say hi. Right. Yeah. It's a good sign that she's already wanting to introduce you to her friends. That's what I thought. It sounded like, man, I'm, I'm really in there this time. So a couple of minutes later, a very good looking guy shows up and the only face on the little blanket that we have is on the other side of me, so now I'm in the middle of them.

The movie starts and then as we're about to watch it, she whispers in my ear, this is my ex. What? Wait. Oh my God. Wait, her ex texted him. Her ex boyfriend? Yeah, so I had to watch the movie with her ex.

Oh my God. What, you stayed, bro? I have so many questions. Well, they're on his blanket. What is he gonna do? I'd be like, it's my blanket, I'm leaving. Why is the ex there alone anyway? Let's hold on, maybe it gets better from here.

Oh goodness. Does it? It does not. Oh. Okay, okay. What happened? What? They're laughing at parts of the movie together

that I'm not laughing at because they have some history of inside together that I'm not laughing at because they have some history of inside jokes that I don't even understand. Here's the bad part. At one point she reached around my back and rubbed his shoulder. Oh my God. Maybe there was like a spider or something. She flicked it off.

This is bad, bro. Why are you wanting to call this woman? She sounds terrible. Somehow the woman in the Philippines sounds better. It doesn't sound like this girl's giving you the attention that you deserve and that you want for a day. Or the respect. Why would you want to reach out to her? I really liked her. I thought she was nice. I thought we had a good chemistry.

I mean after the movie I was like, so that's your ex, huh? But she said we'll always just be friends. So I mean that did probably give you hope that she was still interested in your ex, huh? But she said, we'll always just be friends. So I mean, that did probably give you hope that she was still interested in you, though, right? Her saying that. Well, that's what it sounded like to me. She was trying to make sure I understood. They're just friends. Okay. Well, that is good.

At least she's like explaining, like, I know this looks weird, but I want to reassure you. Yeah. That could be nice. So nothing since? No, and I really would love another chance with Sammy. I like her I think she's the one should be asking for another chance with you or her ex maybe yeah It would be probably nice to get an opportunity to a date without an ex-boyfriend sitting directly next to you that would probably help

I prefer to sit in the non-ex section. Yeah You've been on so many dates recently and none of them have just been one-on-one with the woman in front of you. We gotta hook that up for you. Randall! I mean at least get you some answers because clearly you're looking for help here. Yeah, I am. I really want them to person that likes me, I like them, so is there something I need to do to fix that or improve it. I want to hear it You don't need to fix anything about yourself. You're perfect the way you are Randall. Maybe he does We all could use growth Jeff

Perfect we're gonna try to help Sammy see how amazing you really are when we call her and try and get you your second date Update that's coming up right after Brooke reaches around Jose to scratch my shoulder Okay, never mind we'll just do it after this and get you your second date update that's coming up right after Brooke reaches around Jose to scratch my shoulder. Oh wow. No? Okay, nevermind. We'll just do it after this. Second date update. If you're just joining us, we've got Randall on the phone, a friend of the show who's been unlucky and love lately. He's back because his latest date was with a woman named Sammy which also turned out to be pretty unlucky Because Sammy's ex was at the outdoor movie theater where they both were at and then invited

Yeah invited to join them right that was the really weird part Oh my god Randall like the cream in their Oreo sandwich because he ended up sitting between them for the entire film Which he stayed for yeah It! I have no idea how! It's not exactly your ideal first meetup. No! And Sammy's not responding now. Is she back together with that ex-boyfriend? We don't know.

We might find out here in a second. Randall just wants to understand if he's doing something wrong on these dates. I just kind of want to find find out what am I doing wrong? I just think I have a big heart and a lot to offer. Not only that, but you're putting in the work. Like you are trying to do different things, change the way you're dating, even learn from this experience.

Yes, absolutely. God, I'm frustrated for you. Yeah. I think- This is like the good guys finish last kind of motto. It's like, you know, there's a guy out there who really does want love and really is trying and yes, it's like helpless well not today Finish first or at least get some explanation for why he can't win yeah You guys are my best friend

friend Try not to think that's a sad thing but hey You know what best buddy we're in this together I'm gonna dial her number right now here we go Hello hey is this Sammy Hello? Hey, is this Sammy? Yes. Hey, Sammy. We're calling from a radio show. We're called Brooke and Jeffrey in the morning.

Hi, Sammy. The whole show's here. I was hoping nobody would talk and Jeff would look crazy. Like, we're from a morning show. Thank you for speaking. I really do radio shows. Sorry. You don't do radio shows?

I don't like to talk on radio shows. We've never gotten that. Oh, yeah. I'm sorry. I'm sorry. I'm sorry. I'm sorry. I'm sorry.

I'm sorry. I'm sorry. I'm sorry. I really do radio shows. Sorry. You don't do radio shows. I don't like to talk on radio shows. We've never gotten that. Oh, yeah. That is that is a stance. I look, I totally understand that. And listen, we won't air this unless we have your permission to do it. Yeah. But this is a segment. It's called a second date update. I've heard about that before. Yeah, they're pretty popular. Yeah, thanks. Maybe he's out on TikTok or something. Yeah. Yeah.

It's cool. Interesting. Definitely interesting. It is and you should take it as a compliment because it means somebody out there is trying to get a hold of you. I want to know. I'll play along. Okay. Well, I'll just tell you it's a guy that you went out with recently named Randall My god I'm gonna take that as a fun excited laugh

Like it was the weirdest day I've had Could you tell us how you felt it was weird cuz we've heard a little bit from Randall's side We'd like to get like your perspective on the night. Yeah, we know outdoor movie picnics super fun Yeah, it was actually like a really sweet idea. I was like wow this guy really put a lot into the effort but my the effort, but my ex was there and he texted me, I'm over near the lemonade stand. Wait, how did he know you were there? He saw me, I guess from across the way.

Okay. Oh, okay, so he's the one who initiated the conversation with you. Dude, how rude, you were obviously on a date. Like you're showing up with a guy. You know, I don't really think my ex knew I was on a date. And Randall is such a sweetheart. He's like, why don't you just invite him over?

But when we spoke to Randall, he told us that he was under the impression it was just a friend of yours. Yeah, you didn't specify. Oh, well, he was a friend, but he was my ex friend. Okay, so you didn't tell him. I wanted to tell him, but it all happened so fast. And the movie just started and he sat down right next to us.

Oh my God, so awkward. All right. So, oh, that makes me feel better though, because it sounds like you weren't trying for this interaction to happen. Absolutely not. I thought he would leave but he didn't. Too many nice people that can't say no. So clearly that wasn't a malicious move on your part Sammy but I think what Randall's confused about is if you liked him so much and you're trying to be so sweet to him why aren't you calling him back for

another date? Well it was kind of weird because he told me that it was a movie but he wouldn't tell me the name of it. And he said it was a historical piece but guess what movie it was? What? Fast and Furious. That's not historical. Wait, was that a joke? Are you saying that you're not calling him back because he misrepresented what film was

being shown? No, I just, I thought it was like weird. Like my ex and I were just laughing. Wait, you had told your ex like, oh my God, this guy thinks it's a historical piece and we're joking about him? No, he told us both at the same time and he was backing it up with all these facts. Randall told you both that it was historical. Oh, wow.

My ex is looking at me like, who is this guy? Oh, okay. He's not your type. It's just, yeah. Okay, well, Sammy, thank you for telling us your side of the story. Wait, hold on, hold on. I need to, let me speak my piece. Oh, yeah.

We'll get there. Whoa. We were getting there. Okay. Yeah. Who is that? Yeah, that's Randall. Hold on. I need to let me speak my piece Yeah It's me It's random listen, it's actually based on a true story. You guys do know that right? Is it yes, the movies are actually based on street crimes that were happening in LA in the 90s Do you guys think Vin Diesel was the very first person to rob a semi truck going that fast on the freeway? No! Sorry but I did not know that. Yes! If you read the forums that I'm a part of, the movie ones on Facebook, we all know it's true.

We talk about it all the time. I don't know that we should believe forums on Facebook. Hey they have Tokyo Drift right? We should worry about Tokyo in that. I don't know. And all the time forums on Facebook That's true yes It happened in Tokyo as well. That's why they made a movie about it Or rampant everywhere. I think I think what you need to do Randall is actually talk to Sammy here That's exactly not about yeah, like don't don't have to convince us, you have to talk to Sammy. You know that I'm a good guy. I didn't get jealous when the guy came over your ex. I thought it weird, but I totally understand that you're a nice person too. And I'm just going to be honest and straightforward with Sammy. When we're sitting there watching that movie, you may not have believed me, but your ex sure did. Now, if you could be

with a man like that, that believes the truth now. I think you should be with me as well The pitches if you can date your ex you can date me Two fellow truth finders No, I'm sorry to break it to you Randall, but he did not buy it either. We talked to each other over text He did not buy it either. We talked to each other over text You know what he probably just trying to make you feel better cuz you didn't believe it It's like when you talk to those people that believe the earth is flat and you're like, you know what you're right it is He's a good guy He has some funny quirks.

We'll say that this could be a cute story you guys tell later, or something that you make fun of them for in a relationship, you know? I'm going to tell you what, man, nobody else that I know is making fun of Sacks and the Furious. OK. Yeah, well, maybe the benefit is you'll actually learn some interesting things by giving him another chance. Also, we're his best friends, guys. Here's a know-how. I, we're his best friends, guys. Here's a new lobby. I could send you guys documents, so many. Honestly, we need to stop talking about the true crimes that have happened on the streets of LA and focus on true love.

Because that's what we're here to do, Sammy. We're here to attempt to connect you and Randall one more time, movies aside. And you deserve to give him another chance. I mean, your out the entire time like this guy like he deserves one more shot Yeah, a one-on-one shot and we would pay for it. I would absolutely Love to go out with Randall As a friend Friend in quotes like she did about her ex You have a big build up. Maybe she means friend in quotes like she did about her ex.

No. Yeah. Oh, yeah. You know, she was a friend. Maybe good to be a friend to hers. All right. No. There's just not any potential.

It's more of a friend friend thing. Friend friend. Oh, OK. Oh, OK. Doubling down on the friend. Yeah. Well, Randall, that's OK. Because you know what?

You have to be friends before you can be romantic. So I still have hope. OK. Well, you were romantic in hers. Well, actually, you can be romantic. So I still have hope. Okay. You were romantic at first. Well, actually you weren't. One of those one in a million moments. Vin Diesel and Michelle Rodriguez were friends in the movie before they got married. Based on a true story.

That's not real events. That's not gonna happen, but Randall, I would love to hang out with you as a buddy. Buddy. Oh, buddy. Oh, god. We're downgrading even more. Yeah. As an acquaintance next time. Just don't call him a pal.

Oh, Randall. Well, Randall, man, I'm sorry. So we've done now two second dates with you, and you've gotten two friends out of it. I'm not feeling down about this, guys. Like you said, I just earned another friend. That's a good attitude. You are so sweet.

And you have us. You're four best friends. Yeah good attitude. You are so sweet. And you have us, your four best friends. Yes, my BFFs. Kelly Harnett spent over a decade in prison for a murder she says she didn't commit. I'm 100% innocent. While behind bars, she learned the law from scratch. He goes, oh God, her and that jailhouse lawyer.

And as she fought for herself, she also became a lifeline for the women locked up alongside her. It's supposed to have been faith in God, but I had nothing but faith in her. So many of these women had lived the same stories. I said, were you a victim of domestic violence? And she was like, yeah.

But maybe Kelly could change the ending. I said, how many people have gotten other incarcerated individuals out of here? I'm gonna be the first one to do that. This is the story of Kelly Harnett, a woman who spent 12 years fighting not just for her own freedom, but her girlfriends too. I think I have a mission from God to save souls by getting people out of prison.

The Girlfriends, Jailhouse Lawyer. Listen 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. There's a famous headline, I think, in the New York Daily News. It's, Teddy escapes, blonde drowns. And in a strange way, right, that sort of tells you. The story really became about Ted's political future, Ted's political hopes. Will Ted become president?

Chappaquiddick is a story of a tragic death and how the Kennedy machine took control. And he's not the only Kennedy to survive a scandal. The Kennedys have lived through disgrace, affairs, violence, you name it. So is there a curse? 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 podcast, or wherever you get your podcasts. Man, we should be so lucky to be like Randall, who's just collecting friends left and right in his life. Not on purpose, but he's doing it You know this guy is so good at self-improvement that one day and maybe when he's a hundred he's gonna be the perfect man Hurt my soul when she called him buddy How cool would it be if Randall does finally find love with us here on the show and we're there to witness it Wow or better yet

We're calling someone who's like I went on a date with this guy Randall. He won't call me back Although it is like Brooke always says almost everyone deserves love She keeps a list that. I don't say that, everyone does. She keeps a list of people who don't. So if you're not on that list, feel free to email us for help with your dating life. And remember, you can listen to all of our second dates on our podcast

at Broken Jeffrey, wherever you listen to them, and on our YouTube page. Check it out. The Girlfriends is back with a new season, and this time I'm telling you the story of Kelly Harnett. Kelly spent over a decade in prison for a murder she says she didn't commit. As she fought for her freedom, she taught herself the law.

— He goes, oh God, Harnett, jailhouse lawyer. — And became a beacon of hope for the women locked up alongside her. — You're supposed to have faith in God, but I had nothing but faith in her. — I think I was put here to save souls by getting people out of prison. The Girlfriends, Jailhouse Lawyer. Listen on the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Join iHeart Radio and Sarah Spayne in celebrating the one-year anniversary of iHeart Women's Sports.

With powerful interviews and insider analysis, our shows have connected fans with the heart of women's sports. In just one year, the network has launched 15 shows and built a community united by passion. Podcasts that amplify the voices of women in sports. Thank you for supporting iHeart Women's Sports and our founding sponsors, Elf Beauty, Capital One, and Novartis. Just open the free iHeart app and search iHeart Women's Sports to listen now. I'm Bob Crawford, host of American History Hotline, a different type of podcast. You the listener, ask the questions.

Did George Washington really cut down a cherry tree? Were JFK and Marilyn Monroe having an affair? And I find the answers. I'm so glad you asked me this question. This is such a ridiculous story. You can listen to American History Hotline on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. I'm Ian Pfaff, the creator and host of the Uncle Chris podcast.

My Uncle Chris was a real character, a garbage truck driver from South Carolina who is now buried in Panama City alongside the founding families of Panama. He also happens to be responsible for the craziest night of my life. Wild stories about adventure, romance, crime, history, and war intertwine as I share the tall tales and hard truths that have helped me understand Uncle Chris. Listen now to Uncle Chris on Will Ferrell's Big Money Players Network on the iHeart Radio app, Apple Podcasts, or wherever you listen to podcasts. I knew I wanted to obey and submit, but I didn't fully grasp for the rest of my life what that meant.

For my heart podcasts and Rococo Punch, this is the turning river road. In the rest of my life what that meant.