Brooke and Jeffrey: Second Date Update - Second Date Update Classic: First Date Redate

Episode Date: November 26, 2025

The guy in today’s Second Date Update has been on the show before, but today he gets the special opportunity for a First Date REDATE!See omnystudio.com/listener for privacy information.

Hi, Kyle. Could you draw up a quick document with the basic business plan? Just one page as a Google Doc and send me the link. Thanks. Hey, just finished drawing up that quick one page business plan for you. Here's the link. But there was no link. There was no business plan. I hadn't programmed Kyle to be able to do that yet. I'm Evan Ratliff here with a story of entrepreneurship in the AI age. Listen as I attempt to build a real startup run by fake people. Check out the second season of my podcast, Shell Game, on the IHeart Radio app or wherever you get your podcasts. On this week's episode of next chapter, I, T.D. Jake, sit down with Denzel Washington, a two-time Academy Award-winning actor and cultural icon for a conversation about change, identity,

and the moment everything shifted. I mean, I don't take any credit for it. It's nothing I did as special, you know, did knock down a few pegs and recognized. it, but I just didn't put me first. I just put God first, and he's carried me. Whether you're rebuilding, reimagining, or just trying to hold it together, this one will speak to you. Listen to the next chapter podcast on the I Heart Radio app, Apple Podcast, or wherever you

get your podcast, new episodes drop weekly. Don't miss one of them. of them. The show was ahead of its time to represent a black family in ways the television hadn't shown before. Exactly. It's Telma Hopkins, also known as Aunt Rachel. And I'm Kelly Williams or Laura Winslow. On our podcast, welcome to the family with Telma and Kelly. We're re-watching every episode of Family Matters. We'll share behind-the-scenes stories about making the show. Yeah, we'll even bring in some special guests to spill some tea. Listen to Welcome to the Family with Telma and Kelly on the IHeart Radio app, Apple Podcast, or wherever you get your podcast.

A man with Down syndrome tries the impossible, the grand slam in turkey hunting. Four, 53 hits, we're legal shooting light. And he gives us this one last gesture. And he pitches off. And when he pitches off, he flies right into the gun barrel. I said to the cameraman, do you have it? He said, shoot him. I said, Justin, shoot.

You can download this episode and others from Lines and Tines with Spencer Graves on the IHartRadio app, Apple Podcast. or wherever you get your podcasts. In sitcoms, when someone has a problem, they just blurt it out and move on. Well, I lost my job and my parakeet is missing. How is your day? But the real world is different. Managing life's challenges can be overwhelming.

So what do we do? We get support. The Huntsman Mental Health Institute and the ad council have mental health resources available for you at loveyourmindtay.org. That's loveyourmindtay.org. See how much further you've got. can go when you take care of your mental health you know most businesses love when customers come back

when our customers come back it means that we failed them yeah that's just yeah that's what it means but we got a guy back for a second date today in your classic uh you may have heard him before so that's coming up in just a second but let's start with your comments yeah rosy said weird question but have y'all ever done a meet and greet i feel like that would be awesome Love the show. We haven't done a live event in a while. We used to take listeners to Vegas. Oh, my God, you guys.

It was so fun. We're going to try to bring that back. I know. That was great. Yeah, we can't do it now that Alexis is here. Of course they stopped when I got hired. No, you're a liability. They didn't have a big enough budget.

Yeah. For alcohol. Yeah, exactly. Exactly. All right. Well, we will get something on the books for you so that we can all meet up and hug each other. We love to meet people. Be one happy family.

But if you see us in a grocery store, say hi. This is Jeff. Like maybe just wave. He's awkward. Just don't expect anything but awkward small thoughts. There you go. Yeah. Say hi. Yeah.

All right. Your second date starts now. Second date update. Out of all the second dates we've done, I mean, we're talking hundreds or thousands even. I think tens of thousands. Yeah. Possibly.

I mean, seriously. I know every once in a while, I say this is a first. Oh, yeah. But this one really is. Oh, you don't mean it. the other times? Like, what does that mean? No, I mean it those other times, but this time I really mean it.

Oh, you know, I don't believe you. Because we have a return caller. His name is Zach. And you might remember he was on the show a while back, told us about his mobile bartending business that he does for parties and events. Oh, like weddings and stuff and he made pretty good money doing it. Exactly. Last time that he was on, he wanted us to call a woman named Bethany that he had met at one

of those parties. Well, now he's back. And he wants us to call that same woman, Bethany. Again? Again. What? But she knows us now, dear. Wait, how did the last time go that we called her? I don't think it went well, Zach. Are you okay? Did you hit your head? Because we already did this and she turned you down, right?

Oh, is that what happened? Well, I just ran into her again. And we actually went on another first date. Oh. Wait. That would be a second date, Zach. If you go out with the same girl two times, that's considered two separate dates. I do like two first dates, though.

And I'm kind of upset. She said no to you on our radio show, and then you ran into her in person, and then she said yes? Yeah. Yeah, well, it was like a few months in between when we did that. I didn't realize there's, like, a statute of limitations, you know, where after a certain point, it, like, cancels it resets. Well, it's probably just she had a lot of bad experiences in that couple of months, so she's like, I guess I'll try that guy. Okay, but for those of our listeners who don't know what happened the last time or who, might not remember bethany could you jog our memory just a little bit yeah man i met her while

i was bartending a joint bachelor slash bachelor at backyard party and she was just one of the guest okay right and why did she not like you is that a bad girl i will she said no right yeah he can recap yeah what happened the first time well she said that i uh basically it talked about myself too much and my business too much. Right. That's right. So it didn't work out the last time you were on the show, but now you're saying you ran into her again recently. Yeah.

What happened in the second meetup? Well, it's kind of funny because I was bartending another bachelorette party. Oh, really? She was at that one, too. Oh, my God. This is like Alexis. How many times is this woman going to be in a wedding? Yeah. I guess a lot of her friends are getting married right now,

so she's bouncing from wedding to wedding. It tends to happen that way. Okay, so what happened when you and Bethany saw each other at this new bachelorette party? Hey, I know you. Was it that friendly? I'd be shocked. First, there was that deer in the headlights where we both just kind of locked eyes and froze for a second. How did the interaction go?

Well, I didn't open up very well. I started with, you know, hey, it's funny that a lot of your friends are getting snatched up and you're still single. Oh, that's a real. You said that to her? I don't know. I think she may like it. Yeah. I tried to stop it as it was coming out, but it didn't work. Oh, my gosh.

What did she say back? Well, she said something like, well, there you have it. That's why I didn't want another date with you. Oh, yeah, just reconfirming. Well, the sparks are just flying between you two right now. The romance is right. Girls love being a little bit of mean. So you did get a date.

How did you pivot? Well, it wasn't really a date officially. It was like we were having to be. We were hanging out at the Bachelorette party while I was on break, and then we were hanging out in this garden area, and we actually kind of made out a little bit. Wait, what? Did you not have to work?

It's his own business, Alexis. He makes his own rules. I'm like, did the bar close halfway through the park? Just open 20 beers and leave him on the counter. You got a makeout. I did. I got a make out. Okay, of course she did, because she'd been drinking,

and you pointed out how lonely she is. So she thought the need to prove you wrong, probably. Was it like super drunk makeout, or did you guys actually connect? Yeah, go into the details for Brooke. How much time? What button did you unbuncted first? I mean, I wouldn't interpret a drunk makeout as someone's interested in me, I guess. That's true.

She could just be like, yeah, it was just a fun. Especially any wedding scenario. And after they've turned me down. Yeah. I beg to differ. I think she was definitely interested. Okay. What gave you those?

vibes. Probably the makeout. Yeah, I mean, it does seem like there were sparks flying because she didn't pull back. She seemed to be into it. And I was certainly into it. Okay. All right. Okay. But now you're here. Yeah.

So you're saying that she's not responding to you after your second Bachelorette party makeout. That's correct. We're back down to square one. This bag is square one. Oh, man. Dude, I am just dying to talk to her because she is going to be like, what? You are

calling me again. She's going to know. Yeah, she's going to know. She doesn't. Yeah, and that's what's funny. That's what makes this an actual first. We have two of the exact same people

that are being called on the second date update and hoping that the second time goes better than the first. What do we do? Just go, okay, remember last time? Have you reconsidered? Yeah. Oh, okay, bye. Could you answer differently?

Yeah. I mean, what's a strategy here? We should get her to talk about this last date and what her impression was, right? Yeah, I mean, we'll just see if she even answers because she has our number two from the last time that we called. Yeah, I doubt anyone saves it.

Good point. We're going to find out we're going for the very first time a second date update redo. Will she answer? Is this going to work out? It's a mulligan. It's coming up. We'll make that call right after this. Second date update. The great Yogi Berra once said I'm getting deja vu all over again.

And I think that's what I'm feeling right now. Who was Yogi Bear? Would you like a sports guy or something? He was the Hey Boo Boo? How you doing? No, that's Yogi Bear. Oh, that's a cartoon. That's what you said. I think Yogi Berri is like, yeah, a baseball player, right?

You guys are so embarrassing to work with. Why are you doing this person anyway? You don't know anything. Look, the thing is I'm having that deja vu feeling because we're having the exact same two second daters back on again. So you'd think the title of this would be third date update, but not according to our listener, Zach. I thought we could call it Groundhogs Day. Oh, Yogi Barra.

Maybe. Go straight for the guy. No one's going to understand that. If you remember, Zach, he's a mobile bartender who met a woman named Bethany at a joint bachelor-bachelorette party he was working. Bethany said no to us the first time that we called her. Yeah, I mean, very clearly. But fast-forward months later, they meet again at a different bachelorette.

party, end up making out, and now she's not texting him back. Okay, there's no date in any of this story. Let's remember that. Making out is pretty close. No, God, no. I mean, Jeff, do you know how many dudes I made out with that I didn't even know their names? It's interesting, the things that you choose to brag about.

I know. I'm not bragging, I'm just saying. Like, that's not real life what you're saying. I wonder how Bethany is going to feel when we call her, and if she answers, she hears our voices again. Like, Zach, doesn't this feel? weird to you at all? You seem so calm. A little

bit. I mean, come on. Things happen for a reason and the fact that we ran into each other again just kind of sparked it for me like, you know, maybe there is something here. Maybe fate stepping in. No, that's nice. I think that's a good way to interpret it. And if not, you're a chill guy. And Brooke

mix out with chill guys all the time without knowing their names. I'll make up with uptight guy. Whatever guy. I mean, I'm married now, so I can't. Yeah, well, before. He's also a chill guy, though. We'll see. Let's just Call her. We'll see if she picks up. Here we go. Hello. Hi. Is this Bethany?

It's so awkward for us. Hi, Bethany. It's your favorite morning show. Remember us? No, no, no, no. No. No, no, it's good. I don't. No. It's like a horror movie.

Hey. Maybe we should just start to ask for a review of how the first time was going to win. I mean, it's not you. It's not you. It's me. Welcome back to the show, Bethany. No, no. Bethany, Bethany, Bethany, we've been here.

We've done this. I'm good. No, Bethany, you have no idea what we're even calling about. No, I do. You know I do. You know I do. Don't make me do this again. No.

Bethany, look, I hear you. I really. want to respect your wishes, but we have a job to do on this show. Just like a certain strapping hunk of a man who was doing his job serving you drinks recently at a bachelorette party. Oh, yeah, we're back.

You know, Zach? I've been trying to forget, yes. Bethany. We heard the second time was way smoother than the first. No, no, guys, it was a mistake. It was a huge. Wait, I'm talking about, wait. The makeout session was a mistake?

Yeah, obviously. Are you sure? Because it is interesting that the two of you keep randomly running into each other when you're at your most vulnerable, Bethany. Yeah. All of my friends keep getting married and apparently only no one bartender. Are you shocked? Like, what were you thinking the first moment you saw, Zach? I need to talk to the maid of honor at the next party I'm going to.

And this doesn't happen again. Who are you booking for the bar? Wasn't there, like, just a little bit of you that was excited to see him? I mean, I guess a little bit because I did end up making out with him. Okay. Yeah. See? The glimmer of hope.

But it was like the tiniest, I mean, the tiniest, the tiniest. Okay. Well, we want to talk to that teeny, tiny little part of you. Yeah. And reintroduce that tiny part of you to Zach, who you know is already listening and desperately wants to talk to you. Oh, my God. I forgot. That was how it works.

Yeah. Zach, you there? Yeah, here we are. Back again. What are you doing? I told you that that was a one-time mistake. You said that? He said it was a good mistake, though.

I do not remember saying that part. I just remember saying it was a mistake. I mean, honestly, I made up with a lot of guys that night. So I wouldn't say. that it was like that I was probably the last guy you made out with so you know I must be the ringer does that count the ringer

is that the part of the lineup you want to be in I'm thinking you were kind of me you trusted me to call you an Uber where you didn't trust anyone else to call one for you because you were the one serving all of us drink everyone else was drinking I mean Bethany what we were just

talking about before we called you is stuff like fate and destiny things happen for a reason oh no that's a little thick Jeff I think you know before that I was just being drunk at weddings yeah I mean I would I would think that you keep running into each other there's a tiny bit of you that's obviously attracted to him why not go on one real date just to give it a shot what's a worse that could happen I mean you've already drunkenly made out with him I mean I mean actually did that twice but there is a big difference between drunkenly making out with a and then dating the bartender.

Dating is it one date. We're just asking for one date. That's it. One chance. One moment. Come on. You know he's a good kiss. Oh, yeah.

Good point. We didn't ask her that. I mean, Zach, you're the one who has been calling us all these times wanting to connect with her. I'll give you 20 seconds here to say your piece. Convince Bethany to meet up with you one more time. Okay. You know what? If dating a successful mobile bartender isn't really a dream come true for you, I do have bigger

I also want to integrate mobile karaoke with it as well. That's actually smart playing, Zach. It's much better than the sober karaoke mobile DJ. You can come get your confidence from me and then go ahead and sing your song right after. Dude, all you need is a bed situation and you kind of have a mobile home at this point. Yeah. Pump party, have a drink, and lay down. Is that a selling point for you,

I'm not really sure. One thing you probably don't know about me is that, you know, I was basically raised in a trailer. And for my ninth birthday, I got a microphone in a boom box and I used it. I kind of have a natural sound of my voice as well. I wouldn't be surprised if it wooed you just hearing it. Oh, really?

Wait, you're singing voice is really good. Are we going to hear a serenade? Yeah. Get to woo one, bro. Oh, wow. Hey. Go for you. You've lost that love and feeling.

Oh. Whoa, that loving feeling. All right. Okay. He sounds so fun. Go on one date. Come on. Yeah.

And we'll pay for it. Remember, Bethany. If you say yes, the date's on us. It won't be a wedding. Come on. Do it for the plot. I can't. I'm not saying that, like, I never want to see you again.

but I am going to ask if you are bartending at a bachelorette party for a girl named Sienna next month because if you are, I'm going to have to change my RSVP. Oh. Come on, do it for Sienna. He's a romantic at heart. What a guy. I am. And I'm a book solid, so there's a good chance you'll see me there.

That book solid. Zach, you're her kryptonite. Every time that she's around you, she goes weak. I mean, I don't know if it's him or the mojito, but... He may serve a strong drink. It's the perfect combo. It's all leading you towards Zach. So it might be a no from you now, Bethany,

but it could be possible next month at Siena's Bachelorette party. Third makeouts, Sedge. I say third time on this show. Call back. It's going to be like 51st dates all over again. Finally, the six times she goes, I'll go out with him again. We will call you 100 times until you agreed. I think she's laughing.

Not crying, right? Well, you know, I think fate will lend a hand and do its thing, and I've got a good feeling we'll see each other next month. Oh, my gosh. Get your Uber app open, Bethany. He's going to dial it for you. Oh, my God. Brook and Jeffrey in the morning.

Hi, Kyle. Could you draw up a quick document with the basic business plan? Just one page as a Google Doc. And send me the link. Thanks. Hey, just finished drawing up that quick one-page business plan for you. Here's the link. But there was no link.

There was no business plan. It's not his fault. I hadn't programmed Kyle to be able to do that yet. My name is Evan Ratliff. I decided to create Kyle, my AI co-founder, after hearing a lot of stuff like this from OpenAI CEO Sam Aldman. There's this betting pool for the first year that there's a one-person billion-dollar company, which would have been like unimaginable without AI and now will happen.

I got to thinking, could I be that one person? I'd made AI agents before for my award-winning podcast. Shell Game. This season on Shell Game, I'm trying to build a real company with a real product run by fake people. Oh, hey, Evan. Good to have you join us. I found some really interesting data on adoption rates for AI agents and small to medium businesses. Listen to Shell Game on the IHeart Radio app or wherever you get your podcasts. A decade ago, I was on the trail of one of the country's most elusive serial killers, but it wasn't until 2023 when he was finally caught. The were there hidden in plain sight.

So why did it take so long to catch him? I'm Josh Zeman, and this is Monster, hunting the Long Island serial killer, the investigation into the most notorious killer in New York since the son of Sam, available now. Listen for free on the IHeart Radio app, Apple Podcasts, wherever you get your podcasts. So, yeah, when it comes to Bethany and Zach, we are O for two.

I really thought we were going to get her right there. I thought that she was. like, okay, I'll give him a chance. She's coming around. She's admitted, yeah, he's pretty good kiss her. Yeah, when I'm drunk, I guess. But we're going to get her third time. That's the thing.

O for two is not three strikes you're out. Zach is still in this game for a couple more swings. He just has to like run into her again. Guys, I think we're done. No, we're not giving up. I'm going to tell you. No, Brooke. I was so proud of you during this segment.

I know. I tried. I gave it my bed. I really thought in part one, you were not very on board. Was Zach trying again after the rejection? I think you called him. sad and desperate, but by... I did not say that.

Something like that. But by the end, you were really on board with Zach, pulling for him. I think he's a sweet guy. I do. I just think... Just stop there. Okay. You know, I don't need to say anymore.

Brooke, you are my MVP of today's phone call. Even if it did, and in total utter failure, you can take the MVP on this one. Okay, I guess you're welcome. Good work, Brooke. And remember, Brooke can be the MVP for you if you email the show. We'll call that person who's not calling you back, no matter how many times you've run out to them and they've said no. I'd like to say after twice, we're just going to call it. No. No negative attitudes here. And you won't find any negative attitudes on our podcast either.

You'll find them wherever you get yours at Brooke and Jeffrey. Hi, Kyle. Could you draw up a quick document with the basic business plan? Just one page as a Google Doc and send me the link. Thanks. Hey, just finished drawing up that quick one page business plan for you. Here's the link. But there was no link. There was no business plan. I hadn't programmed Kyle to be able to do that yet. I'm Evan Ratliff here with a story of entrepreneurship in the AI age. Listen as I attempt to build a real startup run by fake people. Check out the second season of my podcast, Shell Game, on the IHeart Radio app or wherever you get your podcasts. On this week's episode of Next Chapter, I, TDJ, sit down with Denzel Washington, a two-time Academy Award-winning actor and cultural icon.

I don't take any credit for it. I just didn't put me first. I've just put God first, and he's carrying me. Listen to the next chapter podcast on the I Heart Radio app, Apple Podcasts, or wherever you get your podcast. New episodes drop weekly. The show was ahead of its time to represent a black family in ways the television hadn't shown before. Exactly. It's Talma Hopkins, also known as Aunt Rachel.

And I'm Kelly Williams or Laura Winslow. On our podcast, welcome to the family with Telma and Kelly. We're re-watching every episode of Family Matters. We'll share behind-the-scenes stories about making the show. Yeah, we'll even bring in some special guests to spill some tea. Listen to Welcome to the Family with Telma and Kelly on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. A man with Down syndrome tries the impossible, the grand slam in turkey hunting. Four 53 hits, we're legal shooting light.

And he gives us this one last test. And he pitches. off. And when he pitches off, he flies right into the gun barrel. I said to the cameraman, do you have it? He said, shoot him. I said, Justin, shoot. You can download this episode and others from Lines and Tines with Spencer Graves on the IHart Radio app, Apple Podcasts, or wherever you get your podcast. When I smoke weed, I get lost in the music. I like to isolate each instrument. The rhythmic bass, the harmonies on the piano, sticky melody. Hey, hey, hey, hey, careful, babe.

There's someone crossing the street. Sorry, I didn't see him there. If you feel different, you drive different. Don't drive high. It's dangerous and illegal everywhere. A message from NHTSA and the Ad Council.