Second Date Update: Too Pretty To Tip

Summary

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Podcast Summary: Brooke and Jeffrey: Second Date Update – "Too Pretty To Tip"

Date: June 10, 2026
Episode Theme:
This episode dives into a real-life dating dilemma brought on by an awkward and revealing restaurant encounter. A listener, Andrew, recounts how witnessing rude behavior towards a waitress led to a first date, only for it to veer off-track after an unexpected and embarrassing discovery the morning after. The hosts help dig into what really happened and attempt to broker a "second date."

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Main Discussion Points & Insights

The Restaurant Incident – Rude Customers and a Meet-Cute

[03:27] – [07:49]

• Jeffrey sets the stage: the number one dating turn-off is being rude to service staff.
• Andrew describes a scenario at a Buffalo Wild Wings-like sports bar: he observes two female customers repeatedly question their waitress ("Do you think you're pretty?") and imply she only receives tips for her looks – then use this as an excuse not to tip her.
  • Quote, Andrew [05:17]: “They kept pressing her... ‘No, come on. You think you're pretty, don't you?’”
  • The hosts react with disbelief and humor, probing whether this was just insecurity or a creative way to skip tipping.
• Andrew feels compelled to counteract the negativity:
  • He tips the waitress generously, telling her it's for her good service, not her appearance.
  • Quote, Andrew [07:13]: "I told her, ‘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 hags.’”
• This supportive gesture leads him to get her number, and they meet up later after her shift.

The Date – Good Vibes, Great Night...But Then, Radio Silence

[07:49] – [09:00]

• Andrew and the waitress, Monica, enjoy a dive bar and she stays over at his place. All seems well, but Monica soon withdraws and becomes unresponsive to his texts.
• The hosts theorize: was it just a one-night stand for her?
  • Quote, Andrew [08:41]: "It turned out to be a one-night stand thing, but I really liked her a lot. I don't want it to be just that."
• Andrew is torn about how to follow up without appearing clingy or “stalker-ish”.

The Second Date Investigation – The Call with Monica

[11:31] – [17:41]

• The hosts get Monica on the phone to find out what happened, approaching the topic with humor and empathy.
  • Quote, Monica [13:02]: "In the beginning, he did make me feel better by coming over and talking to me. He felt like someone I could trust."
• Monica reveals the true source of her discomfort:
  • The morning after, as she gathers her things at Andrew’s, she asks for her pants—Andrew tosses her a pair of unknown women’s underwear. She hadn’t worn underwear that night.
    • Quote, Monica [14:22]: "He tosses me my jeans and a pair of underwear. ...But the only problem was, I wasn't wearing underwear that night."
  • This accidental reveal killed the mood. Monica suspected he might regularly bring women home from the bar.
    • Quote, Monica [15:08]: “Does he do this with other waitresses? ...After that, I couldn't talk to him again."
• The hosts and Andrew grapple with the awkwardness and his cluelessness about the stray underwear.
  • Quote, Andrew [16:08]: “Okay, okay. So, yeah, I’m not gonna lie, I have no idea who those were. But I’m really sorry; I really like you a lot.”

Resolution – Clearing the Air, and a Surprising Second Chance

[17:41] – [18:29]

• Andrew, admitting sincerely to past relationships and the mistake, pleads for a chance to explain.
  • Brooke and Jeffrey encourage Monica to focus on Andrew’s honesty and the effort he’s making.
• Monica is moved that someone went to such lengths to fix a misunderstanding.
  • Quote, Monica [18:19]: “You know what? I haven’t had anyone put in the effort to even try to fix things. So I’ll give you another chance.”
• The episode ends with advice about cleanliness and a fresh start for both.

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Notable Quotes & Memorable Moments

• On Tipping and Service:
  • Brooke [03:37]: “The number one turn off for men and women is if your date is rude or dismissive to the waitstaff.”
• Andrew on the Waitress’ Response:
  • [07:13]: "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..."
• Monica’s Discomfort Explained:
  • [14:22]: "He tosses me my jeans and a pair of underwear. ...But the only problem was, I wasn't wearing underwear that night."
• On the Risk of Being a Cliché or a Player:
  • Monica [15:02]: “Does he do this with other waitresses?”
  • Jeffrey [16:46]: “You just admitted yourself you don't even know whose underwear those belong to.”
• Redemption and Reconciliation:
  • Andrew [17:53]: “Monica, that night...it felt so good. I felt really good with you... I'm hoping somehow you can forgive me for the whole underwear thing...”
  • Monica [18:19]: “I’ll give you another chance.”

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Key Timestamps

• [03:27] – The tipping incident at the restaurant and Andrew’s fateful encounter.
• [07:13] – Andrew explains his supportive action and how he asked Monica out.
• [08:41] – Andrew questions if it was just a one-night thing.
• [11:31] – Hosts call Monica for her side of the story.
• [14:22] – Monica reveals her awkward “underwear” discovery.
• [17:41] – Andrew tries to clear the air and apologizes.
• [18:19] – Monica agrees to a second date, citing Andrew’s effort.

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Tone & Takeaways

• This episode, true to the show’s signature style, blends light-hearted banter, self-deprecating humor, and genuine empathy for those muddling through the minefield of modern dating.
• The story underscores how small missteps and misunderstandings can derail budding connections, but also how openness, apologies, and real effort can salvage even the most embarrassing situations.
• Delivering some laughs but also relatable lessons about assumptions, respect, and taking a chance, the episode is a classic “Second Date Update”—low success rate, high entertainment.

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Transcript

[Hoda Kotb]

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. Joy101 it's a new podcast hosted by me. How to cop me. 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 iHeartRadio app, Apple Podcasts or wherever you get your podcasts.

[Brooke]

Hey everyone, this is Teddi Mellencamp and Tamara Judge from Two T's and a Pod. There's been one scandal that's consumed our lives these last couple of months. We're recapping the three part summer house reunion and as always, we're being brutally honest.

[Monica]

We're dissecting timelines, receipts, blind items and previous episodes.

[Brooke]

Amanda and Wes, watch out. We're not going to be easy on you. Listen to two T's in a pod on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.

[Monica]

You think you're in control until you realize you're not.

[Andrew]

As they're having this gun battle thousands of feet up in the air, many of the bullets start to puncture the aircraft. I thought we were gonna die then.

[Brooke]

The Knife is a podcast about the

[Monica]

moment ordinary lives take an unexpected turn.

[Brooke]

Real people, real stories, and the split second that changes everything. New episodes drop every Thursday on the

[Monica]

Exactly Right Network and the iHeart Podcast Network.

[Brooke]

Listen to the Knife on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Everyone sees me as a football player. But before anything else, I'm human. Every single day, I'm still learning how to live with problems, mistakes, relationships, emotions. Ever since I was born, this isn't a normal podcast. Everything here is spontaneous, real and genuine. Just honest conversations about what it means to be alive. I'm Javier Chicharito Hernandez and listen to Learning to be human on iHeartRadio, Apple Podcasts or. Or wherever you get your podcast.

[Jeffrey]

I actually drive better when I'm high.

[Andrew]

It heightens my senses, calms me down. If anything, I'm more careful. Honestly, it just helps me focus.

[Jeffrey]

That's probably what the driver who killed a four year old told himself and now he's in prison. You see, no matter what you tell yourself, if you feel different, you drive different. So if you're high, just don't drive. Brought to you by NHTSA and the Ad Council.

[Brooke]

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 Brooke and Jeffrey. And thank you so much for finding the Second Date podcast.

[Unidentified Male Guest]

Ashton is stealing the copper underneath.

[Jeffrey]

I gotta move out of my parents.

[Brooke]

Somehow we don't blame you. And I didn't see anything, Ashton. But what did you see in the comments? Alexis Mukhtar said hi. From Afghanistan. I've been listening to y' all for years now. Phone tabs 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.

[Jeffrey]

We frequently here on this show that the number one turn off for men and women is if your date is rude or dismissive to the waitstaff. Yes.

[Brooke]

Yeah, it's bad.

[Monica]

Yeah.

[Brooke]

And how often it happens is wild. Yeah, totally.

[Jeffrey]

And Brooke knows that because she owns a chain of restaurants. So she can be rude to the wait staff because she owns them, but not as a patron. That's not okay.

[Brooke]

That's right.

[Jeffrey]

That's where she draws the line. And she doesn't pay over time.

[Brooke]

No, but I don't mean. I don't even pay minimum wage or benefits.

[Jeffrey]

But look, we're getting away from the point here. My point is one of our listeners witnessed a rude encounter happen at a restaurant and it actually led to a date.

[Brooke]

What?

[Jeffrey]

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.

[Brooke]

But really I was. I was hoping that his date's name wasn't Karen.

[Jeffrey]

Yeah, what was the story?

[Andrew]

Hey, guys, thanks for having me on here first.

[Brooke]

Oh, aren't you polite?

[Jeffrey]

Too polite. I don't like it.

[Unidentified Male Guest]

Answer the question.

[Brooke]

Yay. I guess you weren't the issue at this restaurant.

[Jeffrey]

Yeah. Where did this happen?

[Andrew]

It was in a restaurant. Kind of like a Buffalo Wild Wings type sports bar type thing.

[Brooke]

So a classy place. No, I'm not shaving. I'm not shaving.

[Jeffrey]

Always the most polite people go to those types of places.

[Andrew]

Okay, so I was sitting over at the bar and I hear these two ladies near me. They were asking the waitress. They're like, hey, do you think you're pretty?

[Hoda Kotb]

What?

[Unidentified Male Guest]

Mean girl stuff.

[Brooke]

Maybe they were going to compliment her.

[Unidentified Male Guest]

Like, weird setup.

[Brooke]

What happened next?

[Andrew]

Well, the waitress says, well, I mean, I think I have good days and bad days. You know, like any normal person would, Right? But they kept pressing her and they were saying, no, come on. You think you're pretty, don't you?

[Brooke]

What? Jeez. 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.

[Andrew]

Well, they actually didn't do that.

[Unidentified Male Guest]

Oh, no.

[Brooke]

That's coming from a place of their own self confidence issues. But okay.

[Jeffrey]

Why? What happened?

[Andrew]

She just responded, like, I mean, today I feel good about myself, you know, like, obviously taken aback. 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?

[Brooke]

What is their hangout? What is. I have never heard anyone say anything.

[Unidentified Male Guest]

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 how pretty you are.

[Brooke]

So bizarre.

[Unidentified Male Guest]

It could be still bizarre.

[Jeffrey]

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.

[Unidentified Male Guest]

Do you feel you do your job well?

[Jeffrey]

Check this box.

[Brooke]

This is so crazy that this is happening.

[Jeffrey]

It's weird for sure.

[Andrew]

Yeah. So then she responds, I think most people tip me based on my service, not my look.

[Brooke]

Yeah, yeah, done. I'm also good at my job.

[Andrew]

Then she brings the check to the ladies, right? And I hear them say, we're not going to tip you because you're pretty. And I'm sure you get tipped a lot because people base that on your God.

[Brooke]

The whole thing was a setup so they could get out of tipping.

[Jeffrey]

Brooke has never been so impressed by

[Brooke]

a move in her entire life. That is awful.

[Andrew]

I know.

[Jeffrey]

It is pretty low.

[Andrew]

It was infuriating just to watch it.

[Brooke]

Just say it.

[Unidentified Male Guest]

Like, I used to be a server. I could see somebody writing this, but to say it to their face and then walk out.

[Andrew]

Yeah.

[Brooke]

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.

[Jeffrey]

I think I'm pretty, by the way.

[Unidentified Male Guest]

I had a double date, so.

[Jeffrey]

No. What happens? Because you said it leads to a date.

[Andrew]

Yeah, it wasn't with them. I Assure you.

[Jeffrey]

Okay.

[Andrew]

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.

[Brooke]

Oh.

[Jeffrey]

Oh, that's right.

[Brooke]

Call it good.

[Jeffrey]

Okay.

[Brooke]

And then you asked her out?

[Andrew]

Well, yeah, kind of. I. After that, I ended up getting her number, and then we met up after her shift.

[Brooke]

Dang.

[Unidentified Male Guest]

That's crazy because a lot of times servers will give out like, a fake number or just be like, yeah, call me. But it's just a good chance out of their hair, like, actually had a date.

[Brooke]

I don't know. I think she was in a low place. She was ready to do anything positive.

[Jeffrey]

Those two other women actually kind of set you up for this. Perfect. But how did it go?

[Andrew]

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.

[Brooke]

Oh, wow.

[Andrew]

All right.

[Jeffrey]

All right.

[Brooke]

What was it like in the morning?

[Jeffrey]

Oh, you're skipping. Okay. Yeah, let's go to the morning.

[Brooke]

I don't know. I don't feel like I always need all the details of what happened at the night. Like, we understand what happens.

[Jeffrey]

Yeah, she was pretty. It was a very pretty scene.

[Andrew]

She sure was.

[Jeffrey]

Okay.

[Andrew]

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 an Uber for her.

[Brooke]

Yeah.

[Andrew]

But that was it. And she's now not responding to my texts at all other than, like one word.

[Brooke]

Do you think that she was just thinking of it as like a one night type of thing?

[Andrew]

Yeah, I mean, I get, you know, it turned out to be like a one night stand thing, 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 stalker territory. I don't want to do that.

[Brooke]

I would agree. I think you come across as kind of a creepy customer at that point.

[Jeffrey]

Unless you wear a mustache as a disguise.

[Andrew]

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?

[Jeffrey]

Well, it's definitely less stalkerish to reach out to a radio station and have us call her on your behalf.

[Brooke]

That's different than showing up at her work, actually.

[Jeffrey]

So I'm Actually, one step above the stalker move. And we're gonna do it when we come back and get you your second date update right after this.

[Brooke]

Brooke and Jeffrey in the morning. Second date update.

[Jeffrey]

Couldn't start part two without playing this song, I feel pretty.

[Brooke]

My mom loves this song.

[Jeffrey]

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?

[Brooke]

Yeah. Is that why you get tipped? Do you get tipped because you're pretty? That's more the tone.

[Jeffrey]

Yeah, just pressing her like, come on, you think you are. You think you're a regular Arlene Fox, don't you?

[Brooke]

My mom is a smoke show. Yeah, I mean, I'm just saying.

[Jeffrey]

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.

[Brooke]

Dude, it was all a setup because they're cheap.

[Jeffrey]

Yeah, well, one of those customers was Andrew, who took the opportunity to swoop in.

[Brooke]

Not one of those two. Yeah, I mean, that was kind of misleading there, Jeff. People weren't listening to the front. He wasn't.

[Jeffrey]

He literally said, I. I'm not tipping you cuz you're pretty. I'm tipping you cuz you give great service.

[Brooke]

That's right. And you deserve an extra tip because those ladies suck. Yeah, he called them hags, actually.

[Jeffrey]

And it sounds like he got excellent service from her later that night back at his place when she stayed over.

[Brooke]

We don't need to do that.

[Jeffrey]

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'?

[Brooke]

Maybe she thought that you wouldn't want more. What have you texted her?

[Andrew]

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.

[Unidentified Male Guest]

You know, 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.

[Andrew]

Yeah, exactly, exactly.

[Jeffrey]

Are you reminding her that you're not texting her because you're pretty?

[Andrew]

Yeah, maybe I should have.

[Brooke]

Let's not do that when we get her on the phone.

[Jeffrey]

I am on the women's side here. Yes.

[Brooke]

It's interesting.

[Jeffrey]

So let's call her. What's her name?

[Andrew]

Her name's Monica.

[Brooke]

Monica.

[Monica]

Okay.

[Brooke]

That is a pretty girl name.

[Jeffrey]

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.

[Monica]

Hello.

[Jeffrey]

Hey, Monica. This is a radio show called Brooke and Jeffrey in the Morning. How you doing?

[Monica]

Oh, I'm good. What is this about?

[Brooke]

I'm actually so glad you're awake because if you are a waitress, then oftentimes you have late nights. Ah, you know, good thinking, Brooke.

[Jeffrey]

Yeah, Good job waking up today. We're proud of you.

[Brooke]

Probably doesn't listen to morning radio very often.

[Monica]

I don't know.

[Brooke]

You see, that's true.

[Jeffrey]

Honestly, we don't really know you that much either. We've just heard about you through a listener of ours named Andrew.

[Monica]

Oh, Andrew.

[Jeffrey]

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.

[Brooke]

Yeah, he definitely felt like the connection was strong enough. It should be more than just a one time hangout.

[Monica]

Well, I don't know how much you know about the whole night.

[Jeffrey]

He did tell us what happened at the bar before the two of you went out.

[Brooke]

Yeah, with those two jerks.

[Andrew]

Yeah.

[Jeffrey]

Yeah, the hags grilling you about being

[Brooke]

pretty and then using that as an excuse not to tip you. I'm mad. Still.

[Unidentified Male Guest]

Geez.

[Monica]

Yeah, that was. That was pretty rough.

[Brooke]

Yeah, I bet. Wasn't it nice that Andrew like, I don't know, kind of saved the moment in a way.

[Monica]

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.

[Brooke]

Sweet.

[Jeffrey]

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.

[Brooke]

Again, why are we emphasizing that part?

[Jeffrey]

Because he's a good person and doesn't see you for just like a beautiful face.

[Brooke]

It's hard to disagree with you when you said it. I mean, 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 you got. He told us you guys got drinks at a dive bar and that was fun enough to go back to his place.

[Monica]

Also, he did tell you that I stayed over at his place.

[Brooke]

Yeah, yeah, you stayed the night.

[Jeffrey]

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.

[Monica]

There was a little bit of like an issue before I left his house in the morning.

[Brooke]

Oh, no, See, I asked him about the next morning and he said there was nothing awkward.

[Monica]

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.

[Jeffrey]

Oh, wow.

[Monica]

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.

[Unidentified Male Guest]

Wait, oh, another women's underwear on the bed? Not his underwear.

[Brooke]

Yeah, I was just laying around.

[Jeffrey]

Yeah.

[Brooke]

Single guy.

[Andrew]

Yeah.

[Monica]

So like I wanted to ask him, like, who's worthy? But I didn't want to make a big deal about it. I. I didn't know what to do.

[Unidentified Male Guest]

So what if they're his sisters?

[Jeffrey]

I mean that's totally logical explanation for it.

[Brooke]

I can see how that would be a big mood killer. Right? Like even though you're not in a relationship or anything, like just have random women's underwear lying all over some guys. Kind of a turn off.

[Jeffrey]

Well, so what's going through your mind when you, when you see that? Like.

[Monica]

Well, I was like, does he do this with other waitresses?

[Brooke]

Like he just follows those mean girls around and then trying to make people feel better after they stiff their waist down.

[Monica]

It didn't feel good because yeah, before that I didn't want a one night stand, but after that I just, I couldn't talk to him again. Yeah.

[Brooke]

Had to have seen the women's underwear and like internally died. Yeah, there's no way he didn't notice.

[Jeffrey]

He thought it was hers, but it

[Brooke]

was on the floor before that then.

[Unidentified Male Guest]

Right, but I mean, but in his head you're right.

[Brooke]

He would know if another woman's underwear happened to still be there.

[Jeffrey]

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.

[Monica]

Oh my God.

[Jeffrey]

Hoping to talk to you.

[Brooke]

He's like a surprise pair of undies on the other phone.

[Andrew]

Hey, Monica.

[Monica]

Hi, Andrew.

[Andrew]

Oh, hey. I'm sorry about this. I'm really sorry those weren't yours. I would you believe me if I told you they were mine.

[Brooke]

Is that. Is that the road we're going to take?

[Jeffrey]

Is that better?

[Andrew]

Okay. Okay. So, yeah, I'm not going to lie. I have no idea who those were. But I'm really sorry that I really like you a lot. And I. I'm sorry that made you feel like trash. Like, I. I'm so sorry.

[Brooke]

He's trying to yell over the top of the lace panties that were on his bed.

[Monica]

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. I don't know if I can move past that.

[Jeffrey]

Okay.

[Brooke]

And.

[Jeffrey]

And you. 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 whose underwear those belong to.

[Brooke]

That was not a good confession, Andrew. Yeah, it means for days and you don't even know.

[Jeffrey]

You're making yourself sound like a crazy player.

[Andrew]

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 here, this is the thing I want to drive home is. Monica, 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.

[Jeffrey]

So now suddenly you do know who they belong to and you just don't plan on seeing them.

[Brooke]

Or he still doesn't know and there's no way for him to see him again because he has no idea who he was. Probably that.

[Andrew]

Guys, you were supposed to be on my side.

[Brooke]

I know, but I feel like we're just trying to give you a. I don't know.

[Jeffrey]

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. Monic.

[Monica]

Yeah?

[Jeffrey]

What's running through your mind?

[Monica]

I don't know. I'm. 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.

[Andrew]

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.

[Brooke]

I think that's okay. That's okay.

[Jeffrey]

First time.

[Brooke]

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.

[Jeffrey]

And if you're open to it, we'd pay for that meetup.

[Brooke]

See, we are on your side, Andrew.

[Jeffrey]

Just one more. If you're willing to give Andrew a chance.

[Monica]

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.

[Jeffrey]

Oh my God.

[Brooke]

I did not see that coming. Just like those underwear.

[Monica]

Yeah.

[Jeffrey]

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

[Andrew]

I attribute it to you guys. Thank you. And thanks, Monica, for giving me another chance.

[Monica]

Okay, Andrew, not that I'm encouraging that we go back to your place, but just please clean up your room next time.

[Brooke]

Yeah.

[Jeffrey]

Oh my God. She's already becoming your mom, bro.

[Brooke]

Dude, gross. She's all turned off again.

[Unidentified Male Guest]

Jeff, say that if she buys you a hamper.

[Jeffrey]

Run

[Monica]

Brooke and Jeffrey in the morning.

[Brooke]

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[Jeffrey]

It's interesting that Brooks said that she didn't see the yes coming cuz I don't think you. I don't think any of us did, honestly. Yeah, just really goes to show, persistence does pay off sometimes.

[Monica]

Yeah.

[Brooke]

Or she just realized, well, I guess it's just another pair of underwear. It's been worse in my dating life.

[Jeffrey]

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.

[Unidentified Male Guest]

I thought it was going to be the matching bra set that.

[Jeffrey]

Oh, why not? Yeah, the whole. The whole shebang.

[Brooke]

If you guys were paying attention at the beginning. I don't think she does that. The underwear thing, that's not her jam.

[Jeffrey]

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?

[Brooke]

That's right.

[Jeffrey]

Just find us at Brooke and Jeffrey.