Brooke and Jeffrey: Second Date Update - Second Date Update: Too Pretty To Tip

Episode Date: June 10, 2026

Andrew overheard two woman saying something so SHOCKING & RUDE that he had to step in. He thinks he was heroic, but was it actually creepy? See omnystudio.com/listener for privacy information.

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Here we go. Let's do it again. Another brand new episode today for your second date. Oh, my God. Something just fell. I think it's fine. I think the studio is falling apart. But we're still here.

We're still making it happen for you. It's Brick and Jeffrey, and thank you so much for finding the second date podcast. I think Ashton is stealing the copper underneath me. I got to move out of my parents somehow. We don't blame you, and I didn't see anything, Ashton. But what did you see in the comments, Alexis? Muktar said, hi from Afghanistan. I've been listening to y'all for years now, phone taps, and this.

And anywhere I go, my college commute is 30 minutes by bike from my house. And I always have y'all on literally my favorite pod. Oh, that's awesome. I hope you keep the volume a little low so you hear the oncoming vehicles. Yeah, true. You know, be careful out there, all right? Yeah. There you go.

Your brand new podcast starts right now. Brooke and Jeffrey in the morning. Second date update. We frequently hear on this show that the number one turnoff for men and women is if your date is rude or dismissive to the wait staff. Yes. Yeah, that's bad. Yeah. And how often it happens is wild to me.

Yeah, totally. And Brooke knows that because she owns a chance. pain of restaurants. So she can be rude to the waitstaff because she owns them, but not as a patron. That's not okay. That's where she draws the line and she doesn't pay overtime. No, I don't mean, I don't even pay minimum wage. Or benefits.

We're getting away from the point here. My point is one of our listeners witnessed a rude encounter happened at a restaurant and it actually led to a date. What? Andrew, I read your email. Tell us more about the situation that you encountered. Hopefully it wasn't at one of Brooks' unregistered roadside diners. Really?

I was hoping that his date's name wasn't Karen. Yeah. What was the story? Hey, guys. Thanks for having me on here first. Oh, aren't you polite? Too polite. I don't like it.

Answer the question we say. I guess you weren't the issue at this restaurant. Yeah. Where did this happen? It was in a restaurant kind of like a Buffalo Wildwing type sports bar type thing. So a classy place. Oh. Shame on.

No, I'm not shaming. I'm not shaman. Always the most polite people go to those types of places. Okay. So I was sitting over at the bar and I hear these two ladies near me, they were asking the waitress. They were like, hey, do you think you're pretty? What?

What? Maybe they were going to compliment her. That's a weird setup. I don't know. What happened next? Well, the waitress says, well, I mean, I think I have good days and bad days. You know, like any normal person would, right? Yeah.

But they kept pressing her and they were saying, Come on, you think you're pretty, don't you? What? Geez. I mean, please tell me that they followed up with a compliment. Like, we think you're gorgeous. Like the tone isn't as mean as it sounds. Yeah, yeah.

Well, they actually didn't do that. Oh, no. That's coming from a place of their own self-confidence issues, but okay. Why? What happened? She just responded, like, I mean, today I feel good about myself, you know? Like, she was obviously taken aback. Uh-huh.

But then she makes the drinks and she brings them. back on time and everything. She's like really good to them. And then the women are like, do you think people tip you because you're pretty? What is their hang-up? Wow. What is weird? I have never heard anyone say anything like that.

Now I'm thinking it's got to be an attempt at a compliment. Like you're so pretty, you're so pretty. Come on. You know how pretty you are. So bizarre. It is still bizarre. Or it's an episode of undercover boss and they're secretly taping this.

And they're like, come on, be rude to the customer. Do you feel you doing your job well? Check this box. This is so crazy that this is happening It's weird for sure Yeah So then she responds I think most people tip me based

On my service, not my look Yeah I'm also good at my job Then she brings the check To the ladies right And I hear them say We're not gonna tip you Because you're pretty

And I'm sure you get tipped a lot Because people base that on your life The whole thing was a setup So they could get out of tipping Brooke has never been so impressed By you know That is awesome I know.

It is pretty low. It was infuriating just to watch it. Oh. But I used to be a server. I could see somebody writing this. But to say it to their face and then walk out. Yeah. Please tell me you didn't follow them into the parking lot and ask one of them out. And that's why you're calling. I think I'm pretty, by the way.

So anyway, I had a double date. So no, what happens? Because you said it leads to a date. Yeah, yeah, it wasn't with them. I assure you. Okay. So I tipped her big. And I told her, I was like, listen, I'm not tipping you because you're pretty, even though, of course, you are. I'm tipping you because you're a great server and you shouldn't listen to those tags. Oh.

Oh. That's right. Call her tags. That is good. Okay. And then you asked her out? Well, yeah, kind of. After that, I ended up getting her number.

And then we met up after her shift. Dang. That's crazy because a lot of times, service, like, a fake number or just be like, yeah, call me. But it's just to get you out of their hair. Actually, you had a date? I don't know. She was in a low place. She was ready to do anything positive.

Those two other women actually kind of set you up for this. Perfect. But how did it go? I mean, it was good. We went to a dive bar, but we were out pretty late. And then she ended up staying at my place. Wow. All right.

What was it like in the morning? Oh, you're skipping. Okay. Yeah, let's go to the morning. I don't know. I don't feel like I always need all the details of what happened at the night. We understand what happens. Yeah, she was pretty.

She was very pretty scene She sure was So the next morning When she was leaving I thought things were good between us Everything was awesome actually And the mood seemed good and everything And I was helping her gather her stuff

And I even called her an Uber for her But That was it And she's now not responding to my text at all Other than like one word Do you think that she was just thinking of it As like a one night type of thing? Yeah I mean

I get, you know, it turned out to be like a one-night standing, but I really don't want it to be. I really liked her a lot. And I guess I feel like if I go back to her bar, though, I'm going to be in soccer territory. I don't want to do that. I would agree. I think you come across as kind of a creepy customer at that point. Unless you wear a mustache as a disguise. Yeah, I don't know.

I just haven't heard from her through texting. And I don't know what to do now. So what do you guys think? Well, it's definitely less stalker-ish to reach out to a radio station and have us call her on your behalf. That's different than showing up at her work actually. So I'm actually for it. Yeah. This is one step above the stalker move and we're going to do it when we come back

and get you your second date update right after this. Brooke and Jeffrey in the morning. Second date update. Couldn't start part two without playing this song. I feel pretty. That's what this is. My mom loves this song. Because our listener, Andrew, witnessed

a waitress getting basically harassed by two other female patrons at the bar who kept asking her, hey, do you think you that you're pretty? Yeah, is that why you get tipped? Do you get tipped because you're pretty? Yeah, that's more of the tone. Yeah. Just pressing her. Like, come on, you think you are. You think you are a regular Arlene Fox,

don't you? My mom is a smoke show. Yeah. I mean, I'm just saying. And when they left the bar, they told her, we're not tipping you, because you get plenty of other tips from customers who find you pretty. Dude, it was all a setup because they're cheap. Yeah. Well, one of those customers was Andrew who took the opportunity to swoop in. Not one of those two. Yeah. I mean, that was. kind of misleading there, Jap. People were listening to the front.

He wasn't. He literally said, I'm not tipping you because you're pretty. I'm tipping you because you give great service. That's right. And you deserve an extra tip because those ladies suck. Yeah. He called them hags, actually. And it sounds like he got excellent service from her later that night back at his place when she stayed over. We don't need to do that. Andrew felt like it was more of a one-night thing.

But afterwards, she's not being super receptive to his text. So maybe she didn't feel the same. and that's okay if she didn't. Maybe she thought that you wouldn't want more. What have you texted her? I'm just saying like, what's up? I mean, I didn't specifically say, like, hey, let's go get something again. Because she's not really responding.

It feels like you can't start a conversation even. Like you're saying, hey, what's up? How's your day kind of vibe? Yeah, exactly, exactly. Are you reminding her that you're not texting her because her pretty? Yeah, maybe I should have. Let's not do that when we get her on the phone. I am on the women's side here.

Yeah. Really? Yes. It's interesting. So let's call her. What's her name? Her name is Monica. Monica. That is a pretty girl name. Don't say that, Brooke. Don't label her that way. She's more than that. Let's just give her a call.

And we'll see what she's really all about. Here we go. Hello. Hey, Monica. This is a radio show called Brooke and Jeffrey in the morning. How you doing? Oh, I'm good. What is this about? I'm actually so glad you're awake. Because if you were a waitress, then oftentimes you late nights. Ah. You know?

Good job waking up today. We're proud of you. Probably doesn't listen to morning radio very often. I don't know you. Honestly, we don't really know you that much either. We've just heard about you through a listener of ours named Andrew. Oh, Andrew. I don't love how you say that, but maybe there's a reason that you say it that way because

what we're doing here is called a second date update. we're trying to help Andrew figure out if there's a reason that the two of you haven't met up a second time. Yeah, he definitely felt like the connection was strong enough it should be more than just a one-time hangout. Well, I don't know how much you know about the whole night. He did tell us what happened at the bar

before the two of you went out. Yeah, with those two jerks. Yeah. The hags. Yeah, the hags. Grilling you about being pretty. And then using that as an excuse not to tip you, I'm mad still.

Geez. Yeah, that was pretty rough. Yeah, I bet. Wasn't it nice that Andrew, like, I don't know, kind of saved the moment in a way? Well, in the beginning, he did make me feel better by coming over and talking to me, and he felt like someone I could trust, so I gave him my number. Yeah. He told us that.

He said that he told you that he didn't think that you were pretty, that he was tipping you because you were a good server. Again, why are we emphasizing that part? Because he's a good person and doesn't see you for just like a beautiful. beautiful face. It's hard to disagree with me, isn't it? I mean, it's like the words are right and the tone is just weird. He's a good guy. Maybe we could just move on to them hanging out.

Remember, he told us you guys got drinks at a dive bar, and that was fun enough to go back to his place? Also, he did tell you that I stayed over at his place. Yeah. Yeah, he just said you stay the night. We tried not to pry too deep into it because overall he just felt like there was a strong connection, strong enough that you'd hang out a second time, and that hasn't happened, and he's not sure why?

There was a little bit of, like, an issue before I left his house in the morning. Oh, no. See, I asked him about the next morning, and he said there was nothing awkward. Well, he wouldn't have known about it because I didn't make a big deal about it, and I didn't tell him anything. Oh. So what happened in the morning was, as we were getting ready, our clothes were everywhere. and I asked him to toss me my pants

because they were closer to him and he tosses me my jeans and a pair of underwear but the only problem was I wasn't wearing underwear that night. Wait. Oh, another, women's underwear on the bed, not his underwear.

Yeah, that's just laying around to do. That's not joggers. Single guy. Yeah. So, like, I wanted to ask him, like, who's worthy, but I didn't want to make a big deal about it. I didn't know what to do. What if they're his sisters?

I mean, that's a totally logical explanation for it. I can see how that would be a big mood killer, right? Even though you're not in a relationship or anything, like just to have random women's underwear lying all over some guys. Well, so what's going through your mind when you see that? Well, I was like, does he do this with other waitresses? He just follows those mean girls around and then tries to make people feel better after they stip their weight staff.

It didn't feel good because before that, I didn't want a one-night stand. But after that, I just, I couldn't talk to him again. Yeah. But he didn't want to want to one-night-stained either. He had to have seen the women's underwear and, like, internally died inside. Yeah, there's no way he didn't notice. He thought it was hers. But it was on the floor before that then, right?

But in his head, you're right. He would know if another woman's underwear happened to still be there. I don't know what's going through his mind. We should just ask him right now because you don't. know this, Monica, but Andrew's been waiting on the other line listening. Oh, my God. Hoping to talk to you. He's like a surprise pair of undies on the other phone.

Hey, Monica. Hi, Andrew. Hey. I'm sorry about this. I'm really sorry those weren't yours. Would you believe me if I told you they were mine? Is that the road we're going to take? Is that better?

Okay, okay. So, yeah, I'm not going to lie. I have no idea who those were, but I'm really sorry that happened. I really like you a lot, and I'm sorry that made you feel like trash. I see. I'm so sorry. He's trying to yell over the top of the lace panties that were on his bed. Yeah, I mean, I did mean what I said before that I initially didn't want this to be a one-night stand,

but I don't know if I can move past that. Okay. And she was saying earlier, Andrew, she's worried maybe you do this all the time with waitresses all over the city because you just admitted yourself. You don't even know who's underwear those belong to. That was not a good confession, Andrew. Yeah. It means they're on the floor for days and you don't even know who. You're making yourself sound like a crazy player.

Okay. I don't do this with lots of waitresses. I mean, yeah, every now and then I'll meet somebody here and there, but it's not like all the time, you know. And I hear this is the thing I want to drive home is Monica. But that night at the dive bar, after we connected, it felt so good. I felt really good with you. And honestly, I was somewhat sober at that point. So I'm hoping that somehow you can forgive me for the whole underwear thing that I had no idea that was the reason.

And I definitely don't plan on seeing that person again. So now suddenly you do know who they belong to and you just don't plan on seeing them. Or he still doesn't know and there's no way for him to see him again because he has no idea who it was. Probably that. Guys, you were supposed to be on my side. I know. But I feel like we're just trying to give you a, I don't know. Yeah, there's some landmines that you haven't cleaned up along the way.

And we haven't heard how Monica's doing right now. Monica, what's running through your mind? I don't know. I'm thinking a lot of things. You're kind of backpedaling a little bit, and I don't want to dismiss how I feel. Okay. Monica, you shouldn't have to dismiss how you feel. I just want you to hear me out.

Like, I really, really like you. And yes, I've had sex with somebody before, and they left underwear on my name. I think that's okay. First time. I mean, it was a mistake that he made. He sounds sincere that he really likes you, Monica, and he wants to see you again. And if you're open to it, we'd pay for that meetup. See, we are on your side, Andrew.

Just one more if you're willing to give Andrew a chance. You know what? I haven't had anyone put in the effort to even try to fix things with me. So I'll give you another chance. Wow. Oh, my God. I did not see that coming. just like those underwear.

Yeah. Well, congratulations, Andrew. I don't know how you did it, but you dug yourself out of your own hole. Okay. You got yourself a date. I attribute it to you guys. Thank you.

And thanks, Monica, for giving me another chance. Okay. Andrew, not that I'm encouraging that we go back to your place, but just please clean up your room next time. Yeah. Oh, my God. She's already becoming your mom, bro.

Dude, gross. She's all turned off again, Jen, if you say that. If she buys you a hamper, run. Yeah. Brooke and Jeffrey in the morning. Summer is on at Base 31. The Drill Hall RBC stage is packed with big shows, live music, and electric summer nights,

featuring acts like Father John Misty, the beaches and wild rivers. From Can't Miss concerts to food, drinks, art, history, and places to gather across the B-31 district. There's never been a better time to visit Base 31 in Prince Edward County. Plan your visit at Base 301. joy is essential and it's also elusive you can't order it you can't borrow it or simply hope it into life but now there's a new and exciting way to start your journey toward a more joyful existence joy 101 it's a new

podcast hosted by me how to cotby together guys we'll have meaningful conversations with the world's most fascinating people entertainment legends sports icons wellness experts and everyday people will share how they find, allow, and experience joy. And I'll offer some of my own tips and takes on seeking a more balanced and harmonious life. If you're craving inspiration, support, and useful tools to maximize your joy, tune into these candid, uplifting, and moving on-air chats. Joy after a breakup. Joy is an empty nester. Joy after a loss. Joy as a caretaker. This new podcast will speak to you. Listen to Joy 101 on the IHeart Radio app. Apple Podcast or wherever you get your podcasts.

It's interesting that Brooks said that she didn't see the yes coming. Did you? I don't think any of us did, honestly. It just really goes to show persistence does pay off sometimes. Yeah, or she just realized, well, I guess it's just another pair of underwear. It's been worse in my dating life. Yeah. I mean, I would say to him bring her a gift on the next date and it should be a brand new pair

of unused underwear that she could leave at his place next time. I thought it was going to be the matching bra set. Oh, why not? Yeah, the whole shebang. If you guys were paying attention at the beginning, I don't think she does that, the underwear thing. Yeah. That's not her jam.

Okay, well, respect to her then. But whatever your underwear situation is, we can always try and step in and help you with your dating life. Email the show. We'll call that person who's not calling you back. And go check out all of our second date podcasts. They're available to listen anytime underwear on or off. That's right.

Just find us at Brooke and Jeffrey. Joy is essential, and it's also. elusive. But now, there's a new and exciting way to start your journey toward a more joyful existence. Joy 101. It's a new podcast hosted by me, Houdicotby. If you're craving inspiration, support, and useful tools to maximize your joy, tune into these candid, uplifting, and moving on air chats. Listen to Joy 101 on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts. I'm Michelle McPhee, and I've been unraveling the strangest criminal alliance I've ever reported on, a Mormon polygamist and an Armenian businessman.

Multi-million dollar house, Ferraris and Lamborghinis, private jets, a billion dollar fraud. But how long can this alliance last? Tell me what you know. Is somebody coming after me? Listen to Kingdom of Fraud on the Aihar Radio app, Apple Podcasts, or wherever you get your podcasts. I am the Therapy Gecko. I am an unlike licensed lizard therapist who takes phone calls from real anonymous humans about their problems, such as this. Sometimes I'll have my girlfriend pre-chew it spicy food and kind of baby bird it into my mouth. Is that weird? This week on Therapy Gecko, we're hearing all real, authentic human stories about anything,

from relationships to family drama to serendipitous encounters with unexpected people and things. If real people peak your interest, this is the podcast for you. Listen to Therapy Gecko on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Last night, a blown call changed a game. This morning, the internet lost its mind, and nobody's telling you exactly what happened. That's where Sports Slice comes in. I'm Timbo, and every episode, we're cutting through the noise, breaking down the biggest moments in sports and giving you the real story behind the headlines.

And we're going straight to the source, the athletes themselves. Their locker room stories, their reactions in the moment, and the stuff nobody gets to hear. Listen to Sports Slice on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. And for more, follow Timbo Slical Life 12 in the TikTok podcast network on TikTok. This is Michael Rappaport, and my podcast, the I Am Rapaport Stereo podcast, is unlike anyone you've ever heard. If you're looking for strong opinions about sports, entertainment, politics, pop culture, whatever else catches my attention, then subscribe now. This kid, Jafar Jackson, should absolutely positively get nominated for his portrayal as Michael Jackson.

Listen to IAM Rap Report on the IHeart Radio app, Apple Podcast, or wherever you get your podcast.