Brooke and Jeffrey: Second Date Update - Awkward Tuesday: I Don't Love My Boss

Episode Date: February 25, 2025

Our listeners love dysfunctional relationships so much, we didn't wanna deprive you. Here's a segment from our Full Show feed that may have even more drama than a Second Date Update. One of our listeners emailed us for help with a situation SO delicate, that if he can’t figure out a solution, his job might be on the line! It's your Awkward Tuesday Phone Call podcast!  See omnystudio.com/listener for privacy information.

What would you do if mysterious drones appeared over your hometown? I started asking questions. What do you remember happening on that night of December 16th? It actually rotated around our house, looking as if it was peering in each window of our home. I'm Gabe Lenners from Imagine, I Heart Podcasts and Lenners Entertainment. Listen to Obscurum, Invasion of the Drones, wherever you get your favorite podcasts.

Hey y'all, I'm Maria Fernandez. When You're Invisible is my love letter to the working class people and immigrants who shaped me. Season two, share stories about community and being underestimated. All the greatest changes have happened when a couple of people said, this sucks, let's do something about it.

We get paid to serve you, but we're made out of the same things. It's rare to have black male teachers. Sometimes I am the testament. Listen to When You're Invisible on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. I'm Mary Kay McBrayer,

host of the podcast, The Greatest True Crime Stories Ever Told. This season explores women from the 19th century to now. Women who were murderers and scammers, but also women who were photojournalists, lawyers, writers and more. This podcast tells more than just the brutal gory details of horrific acts. I delve into the good, the bad, the difficult, and all the nuance I can find,

because these are the stories that we need to know to understand the intersection of society, justice, and the fascinating workings of the human psyche. Join me every week as I tell some of the most enthralling true crime stories about women who are not just victims, but heroes or villains or often somewhere in between. Listen to the greatest true crime stories ever told on the iHeartRadio app, Apple podcasts or wherever you get your podcasts.

I'm Mark Seale. And I'm Nathan King. This is Leave the Gun, Take the Canole. The five families did not want us to shoot that picture. This podcast is based on my co-host Mark Seale's bestselling book of the same title. Leave the Gun, Take the Canole features new and archival interviews with Francis Ford Kobla, Robert Evans, James Kahn, Talia Shire, and many others. Yes, that was a real horse's head.

Listen and subscribe to Leave the Gun, Take the Canole on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. Hey, it's Brooke and Jeffrey, and this is the Second Date podcast. You found it, yes! So a month ago, two months ago, Alexis? Two.

We tried out the Awkward Tuesday phone call. Yes. Because if you didn't realize, we are a full radio show and we do a lot of other things outside of the second date, and so we're like, okay, y'all love the second date update. We love that. Would you also like this little relationship segment as well? And you guys did.

Oh, my God! Oh, well, baby! Yes, yes! The Awkward Tuesday goes up on Sunday right now, which made no sense. Yeah, and it has been one of the most downloaded segments of the podcast for the last two and a half months. Ooh. So, so in honor of that,

we are gonna add some sort of clarity to the situation. And we are gonna start playing Awkward Tuesdays on Tuesday. Wow. We are geniuses. I know, pretty innovative. So thank you for being here. Thank you for the likes, the follows, the comments. Yes, all of it.

And we're gonna make a little more sense. right now is your awkward Tuesday phone call on Tuesday You know our show really is all about bringing people together Against all odds that's what we try to do getting a ten to agree to slum it with a two Convincing a woman to give her ex-boyfriend one more chance Changed sorry for the 18th time promises. He'll never make out with your mom again four times That was enough So we're all again. We're all about bringing people together That's why one of our listeners asked us for help turning a woman down

a little flummox Although I do have to reject Brooks advances every day, so maybe this is actually right up our alley I'm not hitting on you. Okay, just co-workers It is important for him because if he can't do this, his job is going to be on the line. Oh. You're going to hear why when we do your brand new Awkward Tuesday phone call right now.

It's Awkward. It's Tuesday. It's Awkward Tuesday phone call. Jose recently mentioned on the show how excited he was when he received a text message from me outside of work. Yeah, I was. I'm still on that high, Jeff. I feel like I've heard about this text message more than ever. God, it's so embarrassing.

Oh, Jeff, be Jose's friend. I try to never text people outside of the workplace, especially when I'm drinking. Because I know that anything that I say might come back to haunt me later. Just like it did on the show. So I'll never get a text again. Don't remind me. Don't send me into the dark place again. I thought that was normal. I was not making fun of you. I was happy. Look, we all rock bottom at a certain point and that was mine.

But it's a good lesson to remember because I know our listener Jimmy wishes he had kept his phone in his pocket during a Saturday night out. Uh oh. So Jimmy, welcome to the show. Tell us how this whole ordeal started for you. Oh man, I just want to know what emojis he used. That's what I want to know. That could be worse than mine, man.

Man, I'm going gonna jump right into it. So, I met this wonderful lady on one of the dating apps. Okay. And it was one of those times where we actually clicked. It wasn't just a one and done type situation. We started hanging out for, it was like two weeks straight. Yeah. Nine or ten days out of those two weeks.

We're all one and done people on this show, so we can't relate, but it sounds really nice. Doesn't that feel great when you like immediately meet someone, you immediately click and you feel like you want to, you can't get enough of them. You eventually will, but at first. But I'm guessing we're leading into the fact that she's the one that he texted when he was drinking. Yeah, well what happened? Well, one of the days we didn't hang out, I hung out with my fellas and we were watching a game and they were, of course, asking me, you know, where you've been. We haven't heard from you.

You know, I kind of told them the whole deal. Hey, they must have been so happy for you. Yeah, I mean, they totally were. I mean, they were pushing me and juicing me up. I was convinced that you were going to die alone, buddy. Good for you. They're like trading over bet money. Yeah, I was starting to worry about that same thing.

Yeah, you were worried about it, too. That's awesome. Well, sounds like you have a good group of friends. That's cool. Yeah. I mean, all that was great. And as the night went on, we had a few more drinks. They kept asking me more and more questions. Yeah. And I started getting a more, you know, loose lift. And I kind of told my friends

Which is kind of how I felt that I think this might be the girl I love After only a few weeks Sometimes you just know yeah in this situation it did I mean that's all from the time I woke up to the time I slept she was all I was thinking about Why is it in past tense though? So this is called the awkward Tuesday phone call where does this story turn awkward well, so as that night went on and continued drinking a few shots were involved I believe and They're like dude, man. If you you feel this way have you told her why

don't you tell her no and that was probably the wrong time for them to kind of push me in that way because ever tell a woman that Your life should that be Your wedding day no, yeah, what the healthy masculinity coming from you right now, please tell me you did not admit that to her well I Decided to texture this okay Not even cuz he's drunk. I mean, it's got to be a huge moment. Who hasn't done it, though? Confess more than they should have at a drunken night.

What'd you say? You sent that? Yeah, I mean, it was about a paragraph long. Way, way, way too much. Probably a few typos in there, too, I'm sure. Wait, did she reply? This is the worst part. This is the awkward part. We haven't heard the worst part yet. I wish, I wish that would have been the situation.

I might not even be talking to you all right now. Oh no, there were photos involved too. No, no, no, no. Woke up the next morning feeling pretty raunchy as you can imagine and there was a reply Uh-huh, but the reply Was from my boss your boss Yeah, wait you texted your boss what wait she has the same name no Wait, this is better, right? No, you texted your boss a love confession is not better

No, you texted your boss a love confession is not better. Okay. She doesn't know the whole thing already. Okay, but like Brooke said, who hasn't been there and texted their boss drunkenly and confessed their true feelings for them? What did your boss say? What was the reply back? So she actually said, we'll talk about this next week with a wink emoji. Oh, wait a minute.

Hold on. Hold on. Is she like one of those old people that don't understand how emojis work? Because my mom would have sent like red lips or something. Yeah, the sensual lips get sent by my mom, too. And I'm like, that's nice. Maybe she got like squinty stern emoji with that one. Could that be it?

Is that what you're thinking? Well, I was hoping, but then we ended up having a meeting at the office a few days later and She said that she's feeling the same way about me I love that a manager sets a meeting to tell you that she Did she have a whole PowerPoint presentation ready to share her feelings back to you. This is so embarrassing for her.

And now you guys know why I need your help. So you're telling us in where she's confessing that she feels the same way you don't say anything. Yeah, I was frozen. I did not want to lose my job and I just want things to go back to normal. So I really, really need your help on this one Okay my god so You got me on your team and I'm really good at ruining everything with women

All right Thanks to Jose we might have some hope because we're gonna call your boss and let you talk to her say hey I didn't mean to say I loved you in a text the other night try to get stuff back to normal with your job text your crush though yeah you know we'll let you make your awkward Tuesday phone call to your boss right after this We don't have an HR department here Even with zero repercussions for our actions, we still know not to say I love you to our boss. Although our boss does have a really cute southern accent.

I do love our boss. That's not me trying to put blame on our listener Jimmy, because he did that accidentally during a night out drinking with his buddies. And he meant to send it as an I love you text message confession to the new girl that he'd been seeing. But instead, it went to his boss, who shares the same first name. an I love you text message confession to the new girl that he'd been seeing, but instead it went to his boss who shares the same first name. And the worst part is the boss is actually

into it. So Jimmy, I didn't even ask you what is your boss's name? It's Veronica. Veronica. Okay. So we're going to call your boss, Veronica, here and let you make this call. First we need to get you some advice. So Jose, what are you thinking? You need to tell her that when you texted her the other night, you didn't think twice about it, the fact that you work together. Your passion took over. But if you think about the logistics, she's the manager, you love your job, so I think

you tell her. It's not always illegal to date someone within the company you could just need to go tell management. It's an easy out listen They have HR probably yeah No, just say look I think the logistics aren't gonna work and we got to separate and just stay where we are okay You know you're not telling her that message wasn't for you No, cuz you don't want to let her down make her feel bad You just want to say you know what it's just not meant to be right now. Okay, okay lightly stepping away, Brooke

What do you think well? I mean your goal is you want things to go back to normal and I think you need to give up on that dream Oh because that ship has sailed my friend it is gone So we're going plan B And that's for you to be the villain you got to make it so she can't love you because you Suck I love that you need to tell her you have a secret family Work with her though, she's gonna lose all respect for him Work with her though. She's gonna lose all respect for him. Nah, just respecting the bedroom.

See, here's the thing. And then you say, listen, if you don't tell anyone about the secret family, I won't tell anyone that you're in love with me. I think it's a pretty good idea. Jimmy, how do you feel about those pieces of advice? Are you leaning towards either one? I mean, I guess if I had to choose,

I'd probably go with the Jose one. Yeah, I win again. I'll take that. I'm gonna tell you right now, she's gonna quit her job. I'd probably go with the Jose one. Yeah Tell you right now she quit her job you're gonna be Let's see how this works, I love how Brooke describes honeymooning in the Bahamas is a bad thing But We're gonna step away here, Jimmy. We're going to dial your boss, Veronica, for you and let you make your awkward Tuesday phone call.

Good luck, OK? We'll jump in if you feel like you need a little help. Here we go. Oh, man. Oh, man. Oh. Oh. Oh.

Oh. Oh. Oh. Hello? Hey, Veronica. It's Jimmy. Oh, Jimmy. You know what? Speak of the devil. I was just talking about you. Oh, oh, oh, hopefully good things.

Oh, of course. All good things. By the way, the nine o'clock meeting tomorrow is moved to 1030. I'm going to make sure you got that memo because I want to see you there. Oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh,

oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, Oh, of course. All good things. By the way, the nine o'clock meeting tomorrow is moved to 1030. I'm going to make sure you got that memo because I want to see you there. Oh, my goodness. Veronica, you know, I think before we hook up on that meeting, I think we need something we really need to talk about. I never said we were hooking up at the meeting, sweetheart, but maybe after. Sorry, sorry, I did not mean a hook up at the meeting sweetheart, but maybe after. Sorry, sorry. I did not mean a hookup at the meeting. Look,

look, anyway, let me tell you why we need to talk. You know, the texts that I sent late Saturday night, I do know the tax. Honestly, I don't think I thought the whole thing through. What do you mean you didn't think it through? You are attracted to me, right? Well, yeah, of course I'm attracted to you. I mean, how could anybody not be attracted to you?

But you just needed a little liquid courage. You had that with your alcohol and it kind of opened up your mind and you don't have to worry. Yeah. Very, very hush hush. We don't need anybody at the office to know. And it can be a casual thing. It's okay. I know that I'm older than you.

So we can just have it like you're my boy toy. Did you say boy toy? Oh, it's just a term of endearment. Don't worry. You know, the reason I bring it up, look, I know we both love our jobs and I don't know if you thought about it. I just started thinking about it and I just don't want this to get out in any way and harm either one of us.

Oh, I don't think that you're thinking this whole thing through. You wouldn't be my first experience at the office, sweetie. Oh my goodness. I probably shouldn't be telling this to you, but you know Luke in marketing? Yeah, I know Luke. What about him? Well, we had a little fling for a few months last summer and nobody in the office knows about it.

I mean, don't worry it's not like I cut him off we still do stuff every once in a while but not all the time. I can't. You can't we all can't. What is going on? Hey Veronica you're on the radio right now with a show called Brooke and Jeffrey in the morning. I'm on the radio? Yeah. Yeah. Jimmy is one of our listeners and he asked for help doing this thing called the awkward Tuesday phone call. It sounds like you have a history of. Yeah. Is there any job openings where you work? Yeah, do a lot of people work. Sounds actually like more fun than where we work. No, you guys, you shouldn't be doing this. Guys, look, Veronica is awesome. Do not give her her hard time at all, please no we're not

I think that's Jimmy's job what to give me a hard time This is not the reaction that I was expecting at all I thought she'd be upset or disappointed But I think barist for God's sake. Yeah. If anything, she sounds turned on. I mean, Ginny, this isn't really what you were going for, was it? Look, Veronica, here's the deal. And I should have told you this from the very beginning, and I'm sorry, but I actually have an actual lady I met in the last few weeks who's also named

Veronica that I am in love with and that is who the text was intended for. Your name came up in my list when I started typing V and it was a mistake and I've been process. Yeah, that's a lot. It was a really bad mistake that he made one night, and it kind of just got out of control, and that's why he didn't know how to reel it back in. That's why we're here to help him. And you know, I called the radio show, and they gave me this really bad advice, and that's why we're here right now.

Guess what, Jimmy, it was free. Okay, you didn't pay for it, all right? Well, Jimmy, I don't know what kind of advice they gave you you but that doesn't mean we can't hang out every once in a while You know what I mean, okay? You can't do that why he's already thinking the name Veronica in bed, so why not? Did he mention that he also has a second family that he abandoned overseas? It's too late. We're hanging out. Wow.

Jimmy, I think you need to get your resume together. I mean, I guess. I don't know. It sounds like you're going to get a promotion at this job. I don't know about that. Look, all I want to do is I just want to say, please, please, just go back to normal. Just act like you didn't see the text and let's just act like we used to. But when we used to see each other. OK. Well, does that mean you were not undressing me?

Because I was undressing you when I used to look at you. You were. Lawsuit waiting to happen. I'm asking Jimmy. I'm not asking you female radio personality You bro, yeah something is so antiquated. This is the modern working world Okay, listen if our office had an HR department. I would get that woman or person in here right now That's my man, and I think you need to back up. Oh, that's her man now.

Yeah. Well, uh. This is terrible. Jimmy, it sounds like your boss isn't going to give you much of a choice here, so. I mean, I guess. You've got two special ladies in your life now. Yeah.

A work wife and an out of work wife. Hey, they're both the same name. Yeah, make it easy on you guys. Whatever. Look at Jeffrey in the morning. What would you do if mysterious drones appeared over your hometown? I started asking questions. What do you remember happening on that night of December 16th?

It actually rotated around our house, looking as if it was peering in each window of our home. I'm Gabe Lenners from Imagine, iHeart Podcasts and Lenners Entertainment. Listen to Obscurum, Invasion of the Drones, wherever you get your favorite podcasts. Hey y'all I'm Maria Fernanda Diaz. When You're Invisible is my love letter to the working-class people and immigrants who shaped me. Season two, share stories about community and being underestimated.

All the greatest changes have happened when a couple of people said, this sucks, let's do something about it. We get paid to serve you, but we're made out of the same things. It's rare to have black male teachers. Sometimes I am the testament. Listen to When You're Invisible on the iHeartRadio app,

Apple podcasts, or wherever you get your podcasts. I'm Mary Kay McBrayer, host of the podcast The Greatest True Crime Stories Ever Told. This season explores women from the 19th century to now. Women who were murderers and scammers, but also women who were photojournalists, lawyers, writers, and more. This podcast tells more than just the brutal gory details of horrific acts. I delve into the good, the bad, the difficult, and all the nuance I can find. Because these are the stories that we need to know to understand the intersection of

society, justice, and the fascinating workings of the human psyche. Join me every week as I tell some of the most enthralling true crime stories about women who are not just victims, but heroes or villains, or often somewhere in between. Listen to the greatest true crime stories ever told on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts.

I'm Mark Seale. And I'm Nathan King. This is Leave the Gun, Take the Cannoli. The five families did not want us to shoot that picture. This podcast is based on my co-host Mark Seale's best-selling book of the same title. Leave the Gun, Take the Cannole features new and archival interviews with Francis Ford Cobola, Robert Evans, James Kahn, Tawya Shire, and many others. Yes, that was a real horse's head.

Listen and subscribe to Leave the Gun, Take the Canole on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.