Brooke and Jeffrey: Second Date Update - Awkward Tuesday: Plus One

Episode Date: August 12, 2025

One of our listeners was FORCED to talk about money with his crush, and the reason WHY it’s the topic of conversation might be the craziest part. It's your Awkward Tuesday Phone Call podcast!See omnystudio.com/listener for privacy information.

It's Black Business Month, and Money and Wealth podcast with John Hope Bryant is tapping in. I'm breaking down how to build wealth, create opportunities, and move from surviving to thriving. It's time to talk about ownership, equity, and everything in between. Black and brown communities have historically been lasting life. Let me just say this. AI is moving faster than civil rights legislation ever did. Listen to Money and Wealth from the Black Effect Podcast Network on IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Every case that is a cold case that has DNA right now in a backlog will be identified in our lifetime.

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And left a woman behind to drown. Chappaquitic is a story of a tragic death and how the Kennedy machine took control. Every week, we go behind the headlines and beyond the drama of America's royal family. Listen to United States of Kennedys on the IHeart Radio app, Apple Podcast, or wherever you get your podcast.

What would you do if one bad decision forced you to choose between a maximum security prison or the most brutal boot camp designed to be hell on earth? Unfortunately for Mark Lombardo, this was the choice he faced. He said, you are a number, a New York state number, and we own you. Listen to shock incarceration on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Everyone thinks they'd never join a cult. But it happens all the time to people just like you. And people just like us.

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It's Brick and Jeffrey in the morning. This is the second date podcast. Of course, I'm referring to yesterday's second date where the guy said because she had a nose piercing as I'm staring at Alexis's nose piercing. It's true. Which I had mine pierced for 18 years. Oh, really?

Yeah, the only reason I took it out is because when I was breastfeeding my baby when she was little, she kept ripping it out of my nose. Oh, you would look so good. Oh, my God. It hurts so bad. Oh, yeah, I couldn't imagine. Yeah.

Anyway, my dad was all about it when I got it done. And they're already probably biting you as well. That's like double pain. Yeah, it was double pain. So what are some of the comments we're seeing from yesterday's? Yeah, kind of the same Megan Jones said I got my nose pierced with my dad. Oh, yeah. And Rochelle says everyone knows the universal sign for daddy issues is a lower back tattoo.

Yeah. Is that it? I wonder which one takes over. It's just the universal sign that you went to high school in the late 90s. Yeah, everybody had those. Honestly. And the tan, remember the Playboy tan stickers? All the girls had those.

Or a palm tree or a heart, yeah. Yeah, I used to go to a tanning bed, which don't do, by the way. It's terrible for you in the back of a video store. It was so sketchy. That is. It was so sketchy. Anyway, we're going to awkward Tuesday right now, and so let's get awkward to make it happen. It's brand new and it starts now.

The most uncomfortable topic to bring up in any conversation isn't politics or religion or that hairy growth on your lower back. Hands down, it's money. Oh, yeah, hot topic. And while it's kind of unavoidable, if you're talking with your boss or your roommate, the last person you want to bring it up with is your crush. Ooh. Yeah, no.

But that's exactly what one of our listeners is being forced to do. And the craziest part is why he has. has to discuss it with her. Oh, my God. It's so weird, you're going to hear it in your brand new Awkward Tuesday phone call right after this. It's awkward. It's Tuesday. It's Awkward Tuesday phone call.

It shouldn't happen, but sometimes it does where money comes between friends and ruins their relationship forever. Yeah. It's so easily that can happen. Yeah. Like when I bought Brooke a $70 wine. glass decanter for her wedding. That should pretty much equal out Brooke paying for all of my lunches over the last decade, but somehow she doesn't see it that way.

Is that why you don't pay her ever? I actually got married 13 years ago, so it's been over a decade that I've been paying for lunches. That's your three years too. You see the hostilities that I'm still getting over a decade later? She's totally counting. Now, Brooke and I have been able to work through it, but one of our listeners hasn't had as much success with his friend.

And that's why he needs our help today. Nick, welcome to the Friend Dome. How you do? Hey, guys. Thanks for having me. Do you also host a radio show with your friend, Nick? Turn to your show? No, not yet.

Not yet. Okay, there's potential. Well, tell us about the situation going on that's created issues with you and your friend. Yeah, so I got this coworker. She works in my company, but different floor. So I don't really see her that much. Oh, so this is just a work friend. that we're talking about?

Yeah, yeah. So I've had like a small crush on her for a while. Okay. Oh, that's cute. What's her name? Yeah. Dana. Okay.

Does Dana know you have a crush on her? She does because I actually asked her out at a work event about a year ago. Okay. How long ago? About a year ago. A year ago. Wait. Oh, so it didn't turn into anything.

No, she actually had a boyfriend at the time. So she said, no, thank you. but I would if I wasn't in a relationship. So she was nice about it. Oh, that's cool. That's good. She's direct, right? Yeah.

So fast forward a year later. I'm kind of out of the blue. I get a message from her and she wants me to meet her outside. We have food trucks outside of our building. So she asked me to come meet her outside by the food trucks. So I'm excited. I'm like, I've always liked this girl. You know, I'm still single.

So maybe something's changed. Oh, yeah. Maybe she broke up with her boyfriend. Yeah. You know? Yeah. Yeah. So turns out.

She needed a plus one for a wedding that she was going to that Saturday. Oh. Wow. And a wedding date's a legit invite. That is your opening, right? She's single then? At the time, I wasn't sure, and I really didn't want to ask that question. You're like, if I don't ask, and I don't have to know.

Right. Yes, I wasn't sure, and I just kind of wanted to find out and see, and I legitimately could not say yes, quick enough. Awesome. Okay. I'm still hoping she's single. And so I can say, oh. Yeah. So have you gone to the wedding yet or no?

Yeah, so I canceled my plans. I was excited to go. I had plans already, but they can wait. Totally. Right. So I went to the wedding, and I did find out that they broke up. Yes. The bride and groom?

Oh, that's horrible. You're talking about Dana and her boyfriend. Yeah, dated her boyfriend. Dude, that's awesome. It's all lining up for you. I feel like you had to, like, restrain yourself when she said, yeah, we broke up. You're like, oh. Oh, no.

A little fist pump under the table. I pretended to feel sad about it. Good job. What you're supposed to do. Yeah. And we had a great time. And it was her friend from college's wedding. We were dancing, we were drinking, had a flirty vibe between us.

Cute. This is random. But, like, how were you associating with her other friends? Yeah. I guess that will give you a good read into how the, like, the vibe is between you and her if you're able to get along with her friends. Yeah, mutually. Yeah, yeah.

We were all drinking at the bar, having a good side. I'm good great sign okay where does the money stuff come in I'm wondering like this is feeling like a second date update not a awkward Tuesday call oh I'm getting there don't worry oh you're like me okay okay at the end of the night we had a hug I could have went for the kiss but I didn't you know out disrespect we were drinking and I asked her to hang out next weekend and she said she would really like that cool okay then two days later it happened what did uh oh I got a Venmo request what asking for $150 to cover my wedding guest fee. Oh, a wedding guest fee? From who? It wasn't from her. It was from her. It was from Dana.

Yep. Wow. I've never even heard of that. Did she Venmo the wrong person? I texted her and I said, are you sure this is for me? I thought maybe it couldn't be for me. Yeah. And she said it's for both of us.

Wait, wait. 75 bucks a person. So, wait. I guess it makes sense if the bride didn't like this, she didn't bring a boyfriend. He said wedding gift. It sounds like that she's making him pay for the wedding gift that she gave her friend from college. Is that what you said gift? No, yeah, wedding costs.

Guest cost. Guest, wedding guests. What is that then? I'm not sure, to be honest. Okay. So what is it that you want to do with your awkward Tuesday phone call then? I mean, I kind of just want to know what the costs are for. Why am I paying them?

You invite me to the wedding. It's confusing. Like, I want to know what's going on. It's like her friend. I mean, yeah. It would make sense if he was getting an invoice from the bride and groom directly and that was their issue. But the fact that it's coming from Dana, that makes it really, really weird. Well, it's, and that there's no explanation.

She's treating that like that's an obvious. Yeah. Like, she said for food or for a gift. Or maybe there was, like, a cash bar and you didn't realize. Oh, yeah. You know, like maybe the drinks cost that night. Maybe. Oh.

But he wants to keep the chance of a romantic connection. alive. So we're going to come back and figure out some ways to flirtily sexily ask her. Hey, hey, what's that you sent me all about? And if anyone's going to have a flirty conflict, it's you, Jeff. Yeah. We'll come back with some advice for you for your awkward Tuesday

phone call right after this. It's awkward. It's Tuesday. It's awkward Tuesday phone call. If you're just joining us for the awkward Tuesday phone call, not only is a friendship on the line, but a possible. love connection between our

listener Nick and his co-worker Dana. There's been some unspoken feelings happening there, so when she asked him to be her plus one to a wedding recently, that was his golden opportunity. Oh, he was so excited. The weird part is

afterwards, Dana sent him a $150 invoice to cover their wedding guest fees. We still don't know what that means. Nobody knows what that means. At least of all, Nick, and it just felt wronged him because he was the plus one. He didn't even know who the bride and groom were.

That's why he wanted our help today to bring it up to Dana and figure it out while still keeping his chances with her alive. Honestly, though, Nick, if you really want this woman to like you, maybe the best answer is just eat that $150 and don't make this phone call. That's what I was going to say. No, you guys, this sets the tone for the entire relationship, honestly. She'll know he takes care of his lady. Yeah, she'll like that about you, Nick.

Okay, Brooke, you have better advice for him? What's your idea? I think you should get out of pin and write down my question right now. Seriously. Bro, nobody writes things with pen and paper. Just write on your phone in the notes app. Okay. You need to ask her, Nick, why pay her half?

Oh, yeah. What? Seriously, why pay her half? Because she said that it's for me as well, right? So she invited you. It's her friend. Sure, she should be paying for you. But in the least, why do you have to pay her wedding fee?

make any sense. Are you saying that on a date, Brooke, you wouldn't make your husband Michael pay for stuff? This isn't a date. This is a wedding. And this is her friends. Like, bride and grooms do weird things all the time. But it's kind of a wedding date.

It's like a hybrid. When you and Michael are at a wedding, all bets are off. You guys aren't together. You are separate entities and whatever happens just happens. I see what you're saying, Brooke. I'll keep that in mind. Jose, what's your advice? I don't understand.

Oh, I get it. Jose. You are going to do something really unconventional here, okay? You're going to thank her immediately. Really? Why? Yeah, why? Why would I thank her? Well, this sets a positive tone immediately. You're like, hey, thank you so much for that. I didn't even think to ask if I owed you any money. And then maybe guess what you think it's for rather than accusing her of what it's for. You're like disarming her with a compliment before you come in with a real question. Oh my gosh. I must have got a gas. It must have been a wedding gift. I mean, it could get you the answers you want of what it's for, but it definitely doesn't get you out of pain for it. You know what I mean? You're paying.

But one step at a time. Keep her happy. Keep the vibes positive. What do you think? You feel like that's helping you out before you make your call here? Yeah, I guess. I'm still very confused on why I got a bill. I guess I would all figure out in the moment.

But we've given you the tools to be able to hopefully handle this conversation without making it too awkward between you and Dana. I'm so curious how you're going to feel after you hear her answers. And I wonder what the answer is. 75 each is a pretty good deal for a wedding. Just saying, Alexis. You're lucky that she didn't invoice you to pay for her dress also. Count your blessings, but we're going to dial her number right now. Hopefully she picks up and you can make your awkward call.

But here you go. Hey, Dana, it's Nick. How you doing? Hi, Nick. I'm great. It's great to hear from you. You too. How's everything going? It's going pretty well. Just working like usual, as you know. Yep, yep. Just another day on the grind. So what's up? Are we still getting together for lunch today? Yeah, yeah. I mean, I had a great time the other night. And I want to thank you first for the

invite in the party. I had a great time and I just I kind of apologize for not asking what I owed for the event because I know I got that invoice so I didn't know uh wanted to find out more like what's going on. Oh yeah. Well you know the bride she sent me an invoice and actually charged me $75 for each of us. Um, oh wow. You probably wanted to know that. Yeah. Just kind of came out of nowhere. Usually when you go to a wedding you don't, you know, someone's taking you, you don't really think about paying so but i also just i should have asked if i you know owed anything because i love hanging out with you and you know i never want to draw in between that you know i mean maybe i read the situation wrong i mean i kind of thought that we were on a date and typically whenever i go on

dates guys will usually pay um are you saying you wouldn't want to pay if we were on a date if it was a date i think it would be different i just kind of you kind of invited me and i didn't know if it was, you were considering it a date or if it was, I don't know, just kind of came out of left field. A little context probably would have helped, you know? That's interesting. It kind of feels like you're criticizing how I handled it. I'm not trying to criticize. Just kind of thinking out loud and just trying to get some more information, you know? Well, ever since I broke up with my boyfriend, I've been on quite a few other dates and guys are just notoriously cheap. And that's why I'm just so glad that I'm getting to

spend time with you. You know, you have so much integrity and you really know, how to treat a woman. Well, I appreciate that. So if you wanted to spend more than 150, you know, I did have to Uber home that night, and there were just a couple other expenses. Oh, man. Nick, you're not saying a lot. Is there a problem?

Like, what's going on? So it's a little outlandish. It's a little crazy. it's outlandish it's outlandish to want to take care of me to make sure that I get home safe like you wouldn't just want to spend a little extra money maybe you're not the person that I thought you weren't Nick oh my gosh that is terrible what is this there dude Nick right brooke no not a dick hey what's going on who is that oh hi hello that was so manipulative Dana oh my god we're all very impressed with you, Dana, because

impresses the room. Yeah, you're on a radio show right now called Brooke and Jeffrey in the morning. Hi. A radio show? Yeah. Nick's there too. Nick, why would you do this? This is between you and me. Why would you call a radio show? What is happening? I just kind

of was taken off guard. I was kind of confused on the whole situation, and I needed help. I called them to help me because I really like you, and I wanted to continue our relationship, and I didn't want to make it awkward, so you don't like me enough to pay my Uber to get home safe, so I guess that's clear enough. Oh, wow.

We're even going to go to the wedding and Uber home regardless of he is there. Dana, how does that have any indication on whether or not he likes you? You guys work at the same place. You probably make around the same amount of money. Yeah, that's true. Pay for yourself. First of all, I don't know who the hell you are. And certain women have standards.

It sounds like you have none. No, certain women have independence and you need some. Excuse me? No, do you know what year it is, grandma? Women are supposed to be taking care of. Taking care of. Okay, we're back into the 1910. Okay, Brooke, enough of the pull yourself up by your own bootstraps talk.

It's not that. Pay for, you invited him to the wedding. Let us pull your bootstraps. We want to lift you to greatness. Don't touch me. Yeah, that's better. Okay. Hey, so, yeah, these people were trying to give me a hand, but, you know, I'm sorry, Dana.

I want to take responsibility for it, you know. Yeah. That's nice. That's really nice. I could have been better. Oh, you? Why are you taking blame for this? I mean, Brooke, you're ganging up on her.

You're ganging up on the team. What? And me, I came here as a guest. I don't have to put up with this. Nick, I'm trying to stand up for you. No, he wants to stand up for Dana because he was her date. And so at the beginning of this is what you want. That is how women should be treated.

Thank you, Nick. Okay. We're coming into an agreement here. So at the start of this, I suggested you eat the $150, but it sounds like you need to do a little bit more. How much money are you willing to toss towards her in Venmo to prove how good of a date you are? Whatever she needs to feel comfortable here. Wow. What a good guy.

You're just buying her affection at this point. That is not worth it. It won't last in the end, Nick. But, Brooke, you're not dating anymore. I don't think you have any. You checked out 13 years ago from this world with my $70 wine decanter. As payment for that You know, after this, I'm Venmoing you

a charge for attending my wedding That's just how it's going to be Nick, you're going to cover that cause from me, right, bro? It's about love. I don't have you, but I do have Dana. Dana, you and I are good. Oh, wow. What a gentleman.

Dana, you landed a good one there. Yeah, chivalry isn't dead. What romance. Nick, don't listen to him. I'll see you at lunch. You're paying. Okay. Now you actually do sound like Jeffrey

when we're going to love. You should be so lucky. Jeffrey in the morning. Have you ever wished for a change but weren't sure how to make it? Maybe you felt stuck in a job, a place, or even a relationship. I'm Emily Tish Sussman, and on she pivots, I dive into the inspiring pivots of women who have taken big leaps in their lives and careers. I'm Gretchen Whitmer, Jody Sweeten. Monica Patton.

Elaine Welter-off. I'm Jessica Voss. And that's when I was like, I got to go. I don't know how, but that kicked off the pivot of how to make the transition. Learn how to get comfortable pivoting because your life is going to be. full of them. Every episode gets real about the why behind these changes and gives you the inspiration and maybe the push to make your next pivot. Listen to these women and more on She Pivots, now on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

Welcome to Pretty Private with Ebeney, the podcast where silence is broken and stories are set free. I'm Ebeney and every Tuesday I'll be sharing all new anonymous stories that would your perceptions and give you new insight on the people around you. On Pretty Private, we'll explore the untold experiences of women of color who faced it all. Childhood trauma, addiction, abuse, incarceration, grief, mental health struggles, and more. And found the shrimp to make it to the other side. My dad was shot and killed in his house. Yes, he was a drug dealer.

Yes, he was a confidential informant, but he wasn't shot on a street corner. He wasn't shot in the middle of a drug deal. He was shot in his house, unarmed. Pretty Private isn't just a podcast. It's your personal guide for turning storylines into lifelines. Every Tuesday, make sure you listen to Pretty Private from the Black Effect Podcast Network. Tune in on the IHeart Radio app, Apple Podcast, or wherever you listen to your favorite shows. We don't have Dana on the phone with us anymore, but it sounds like Dana was used.

to more of the traditional style of a relationship where all the men are expected to pay for dates and that's not what everybody wants but it's probably how she was raised and what she is hoping for in a relationship. It just sounds like she's cheap to me. She won't even pay her own bill at her friend's wedding. I think that she knew that her friends were going to charge for that wedding

and she had to find a sucker to pay for it. That's what I think. That's possible, sure. Or it could just be, like she was saying, that's how she was raised, and that's what she expects from a guy. Because he'd consider a date, too. Because I wouldn't even think that's a date. He wasn't sure, but he heard Dana's explanation,

and then he eventually came around on it. Eventually came around. He cowered. He cowered to her, like every woman wants a good man to do. Absolutely. Not right. But look, as long as expectations are laid out ahead of time,

it's really up to Nick to say yes or no. Well, he does finally know. We did help him with that. Yeah. For sure. Because it's his life and he chose to pay for it. And for her life, too. And that's true happiness.

So hopefully we helped him achieve something that he felt was positive. I'm glad you're taking such a noble stance on this. Well, you know, I'm just trying to play the middle. Yeah. So we'll try to do that for you if you need help with your awkward lives, email the show. And if you haven't already, hit subscribe on that subscribe button. Thank you. Everyone thinks they'd never join a cult.

But it happens all the time to people just like you. And people just like us. I'm Lola Blanc. And I'm Megan Elizabeth. We're the host of Trust Me, a podcast about cults, manipulation, and the psychology of belief. Each week we talk to fellow survivors, former believers, and experts to understand why people get pulled in and how they get out. Trust me. New episodes every Wednesday on Exactly Right.

Listen wherever you get your podcasts. It's Black Business Month, and Money and Wealth podcast with John Hope Bryant is tapping in. I'm breaking down how to build wealth, create opportunities, and move from surviving to thriving. It's time to talk about ownership, equity, and everything in between. Black and brown communities have historically been lasting lives. Let me just say this. AI is moving faster than civil rights legislation ever did. Listen to Money and Wealth from the Black Effect Podcast Network on IHeart Radio app, Apple Podcasts, or wherever you get.

Your podcast. So what happened at Chappaquittic? 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. Chappaquittic is a story of a tragic death and how the Kennedy machine took control.

Every week, we go behind the headlines and beyond the drama of America's royal family. Listen to United States of Kennedys on the IHeart Radio app, Apple Podcast, or wherever you get your podcast. I'm Jeff Perlman. And I'm Rick Jervis. We're a journalist and hosts of the podcast

Finding Sexy Sweat. At an internship in 1993, we roomed with Reggie Payne, aspiring reporter and rapper who went by Sexy Sweat. A couple years ago, we set out to find him. But in 2020, Reggie fell into a coma after police pinned him down,

and he never woke up. But then I see, my son's not moving. So we started digging and uncovered city officials bent on protecting their own. Listen to Finding Sexy Sweat on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. 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?

Were JFK and Maryland 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 IHeart Radio app. Apple Podcasts, or wherever you get your podcasts.