Awkward Tuesday: I Don't Love My Boss

Summary

Podcast Summary: Brooke and Jeffrey: Second Date Update
Episode: Awkward Tuesday: I Don't Love My Boss
Release Date: February 25, 2025

In the "Awkward Tuesday: I Don't Love My Boss" episode of Brooke and Jeffrey: Second Date Update, hosts Brooke and Jeffrey navigate one of their most entertaining and cringe-worthy listener stories to date. This episode delves into the complexities of modern workplace relationships, miscommunication, and the unforeseen consequences of digital mishaps.

Introduction to Awkward Tuesday

The episode begins with Brooke and Jeffrey introducing their popular segment, "Awkward Tuesday," which stems from listener engagement and high download rates. Recognizing the demand, they announce the segment's official move to Tuesdays to better serve their audience (02:01).

Jimmy's Predicament: The Accidental Confession

The heart of the episode revolves around Jimmy, a listener who finds himself in a precarious situation. Having met a wonderful woman named Veronica on a dating app, Jimmy's budding romance takes an unexpected turn. After several weeks of consistent dating, Jimmy attends a night out with friends where alcohol plays a significant role in lowering his inhibitions.

As the evening progresses, Jimmy's friends encourage him to express his feelings, leading him to compose a heartfelt text declaring his love. However, in a moment of distraction and intoxication, Jimmy mistakenly sends this confession to his boss, also named Veronica, instead of his intended romantic interest (05:06).

Jimmy: "I decided to text her this. Yeah, I mean, it was about a paragraph. Long way, way, way too much. Probably a few typos in there, too, I'm sure." (08:02)

The Revealing Reply

The next morning, Jimmy anxiously checks his phone, only to discover that his boss, Veronica, has responded. Instead of the expected rejection or confusion, Veronica reveals a surprising side of herself:

Veronica: "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." (16:23)

This revelation adds layers to Jimmy's dilemma, intertwining personal and professional boundaries in unexpected ways.

Hosts' Advice and Attempted Intervention

Brooke and Jeffrey, alongside their co-host Jose, brainstorm ways to help Jimmy navigate this intricate situation. Their suggestions range from straightforward honesty to more creative, albeit humorous, approaches:

• Jose: "You need to tell her that when you texted her the other night, you didn't think twice about the fact that you work together. Your passion took over." (11:59)

• Jeffrey: "Your goal is you want things to go back to normal. And I think you need to give up on that dream. Because that ship has sailed, my friend. It is gone." (12:27)

Ultimately, the hosts decide to assist Jimmy by simulating the "awkward Tuesday phone call," aiming to provide him with a platform to address his mistake directly with Veronica.

The Awkward Call: A Comedy of Errors

In a live demonstration, Jimmy attempts to retract his unintended confession. However, the conversation rapidly becomes more complicated:

Jimmy: "Oh, my goodness. Veronica. You know, I think before we hook up at that meeting, I think we need something we really need to talk about." (14:27)

Veronica: "I never said we were hooking up at the meeting, sweetheart. But maybe after." (15:54)

As the dialogue unfolds, it becomes apparent that Veronica has her own history and complexities, further entangling Jimmy's predicament. Despite Jimmy's attempts to explain and apologize, Veronica showcases a playful yet assertive stance, leaving Jimmy in an even more tangled situation.

Conclusion: Lessons Learned and Moving Forward

The episode concludes with Brooke and Jeffrey reflecting on Jimmy's ordeal, highlighting the importance of clear communication and the potential pitfalls of mixing personal emotions with professional relationships. They emphasize the need for caution, especially when alcohol and digital communication intersect.

Brooke: "This is terrible, Jimmy. It sounds like your boss isn't going to give you much of a choice here." (19:38)

While the situation remains unresolved, the hosts provide valuable insights and a touch of humor, ensuring listeners are both entertained and enlightened.

Key Takeaways:

• Digital Communication Risks: Always double-check recipient details before sending sensitive messages.
• Workplace Boundaries: Mixing personal relationships with professional ones can lead to complicated scenarios.
• Seeking Help: Reaching out to trusted sources, like Brooke and Jeffrey, can provide perspective and potential solutions in awkward situations.

This episode of Brooke and Jeffrey: Second Date Update masterfully blends humor with real-life relationship challenges, offering listeners both entertainment and relatable content.

---

Notable Quotes:

• Brooke: "It's Tuesday. It's awkward. We're going to dial your boss and let you make your awkward Tuesday phone call. Right now. It's awkward." (13:32)

• Jimmy: "I decided to text her this. Yeah, I mean, it was about a paragraph. Long way, way, way too much." (08:02)

• Veronica: "We had a little fling for a few months last summer and nobody in the office knows about it." (16:23)

• Jeffrey: "Your goal is you want things to go back to normal. And I think you need to give up on that dream." (12:27)

Transcript

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[Alexis]

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[Jeffrey]

This is the Second Date podcast. You found it. Yes. So a month ago, two months ago, Alexis 2 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. Yes.

[Alexis]

Yes.

[Jeffrey]

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. 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.

[Jose]

Yes.

[Jeffrey]

And we're gonna make a little more sense. And right now is your awkward Tuesday phone call on Tuesday.

[Brooke]

You know, our show really is all about bringing people together.

[Jeffrey]

Yeah, for sure.

[Brooke]

Against all odds. That's what we try to do. Getting a 10 to agree to slum it with a 2.

[Jeffrey]

That's right.

[Brooke]

Convincing a woman to give her ex boyfriend one more chance.

[Jeffrey]

Oh, come on.

[Brooke]

Yeah, he's changed.

[Jeffrey]

He means he's sorry for the 18th time.

[Brooke]

Yeah, he promises he'll never make out with your mom again. Four times. That was enough.

[Jeffrey]

I believe him.

[Brooke]

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 Brooke's advances every day, so maybe this is actually right up our alley.

[Jeffrey]

Hey, I'm not hitting on you. We're just co workers.

[Brooke]

Whoa, Brooke.

[Jose]

Yeah.

[Jeffrey]

Wow.

[Brooke]

The heat a little bit on the conversation. But 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.

[Jeffrey]

It's Tuesday.

[Brooke]

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.

[Jeffrey]

Yeah, I was. I still.

[Jose]

I'm still on that high. Jeff.

[Jeffrey]

I feel like I've heard about this text message more than ever.

[Brooke]

So embarrassing.

[Jeffrey]

Oh, Jeff, be hobby friend.

[Brooke]

No, 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. I know. Don't remind me. Don't remind me. Don't send me into the dark place again. Yeah, I thought that was normal.

[Jose]

I was not making fun of you.

[Jeffrey]

I was not normal.

[Brooke]

Look, we all hit 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.

[Jeffrey]

Uh oh.

[Brooke]

So Jimmy, welcome to the show. Tell us how this whole ordeal started for you.

[Jeffrey]

Oh, man. I just want to know what emojis he used.

[Brooke]

Yeah, that's what I want to know than mine, man.

[Jimmy]

Yeah, man. I'm going to jump right into it. So I met this wonderful lady on one of the dating apps 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. Nine or ten days out of those two weeks.

[Brooke]

We're all one and done people on this show, so we can't relate, but it sounds really nice.

[Jose]

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.

[Jeffrey]

But I'm guessing we're leading into the fact that she's the one that he texted when he was drinking.

[Brooke]

Yeah. What happened?

[Jimmy]

Well, one of the days we didn't hang out, I hung out with my fellows and we were watching a game and they were of course asking me, you know, where you been? We haven't heard from you. You know, I kind of the whole deal.

[Jose]

Hey, they must have been so happy for you.

[Jimmy]

Yeah, I mean, they totally were. I mean, they were pushing me and juicing me up.

[Brooke]

I was convinced that you were going to die alone, buddy. Good for you.

[Jeffrey]

They're like trading over bet money there.

[Jimmy]

Yeah, I was starting to worry about that same thing.

[Jeffrey]

Yeah, you were worried about it too.

[Alexis]

That's awesome.

[Jeffrey]

Well, it sounds like you have a good group of friends. That's cool.

[Jimmy]

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.

[Jeffrey]

Yeah.

[Jimmy]

And I started getting them more, you know, loose lipped. And I kind of told my friends, which is kind of how I felt, that I think this might be the girl I love.

[Jeffrey]

Whoa, that's so cute.

[Brooke]

After only a few weeks.

[Jeffrey]

I mean, I think sometimes you just know.

[Jimmy]

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.

[Jeffrey]

That's.

[Jose]

So she's probably texted all day.

[Jeffrey]

Why is it in past tense, though? All honeymoon fees has come to an end already.

[Brooke]

So this is called the awkward Tuesday phone call. Where does this story turn awkward?

[Jimmy]

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 feel this way, have you told her? Why don't you tell her?

[Jeffrey]

God, no.

[Jimmy]

And that was probably the wrong time for them to kind of push me in that way because.

[Jeffrey]

No, you're right. I tell her I love her.

[Brooke]

No, you never, ever tell a woman that.

[Jeffrey]

Wait, yeah.

[Brooke]

No point in your life should that.

[Jeffrey]

Be revealed on your wedding day.

[Brooke]

No.

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[Brooke]

Please, please tell me you did not admit that to her.

[Jimmy]

Well, I decided to text her this.

[Jeffrey]

Okay.

[Jose]

Text.

[Jeffrey]

You know what I mean?

[Jose]

Regardless.

[Jeffrey]

Not even because he's drunk.

[Jose]

I mean, it's not to be a huge.

[Jeffrey]

I mean, who hasn't done it, though? Confess. Like, more they should have at a drunken night.

[Veronica]

Yeah.

[Jeffrey]

Yeah. Well, what'd you say?

[Brooke]

Yeah. You sent that?

[Jimmy]

Yeah, I mean, it was about a paragraph. Long way, way, way too much. Probably a few typos in there, too, I'm sure.

[Jeffrey]

Wait, did she reply?

[Jimmy]

This is the worst part. This is the awkward part.

[Jose]

We haven't heard the worst part yet.

[Jimmy]

I wish. I wish that would have been the situation. I might even be talking to you all right now.

[Brooke]

Oh, no. There were photos involved, too.

[Jimmy]

No, no, no, no. Woke up the next morning feeling pretty raunchy, as you can imagine. And there was a reply, but the reply was from my boss.

[Jeffrey]

Your boss?

[Brooke]

What? Oh, yeah.

[Jose]

Wait, you texted your boss what?

[Jimmy]

Wait, she has the same name.

[Jeffrey]

No, Wait, this is better, right? No, you texted your boss. A love confession is not better. Okay, she has a dumb boss already.

[Brooke]

Okay, but like Brooke said, who hasn't been there and texted their boss drunkenly and confessed their true feelings.

[Jeffrey]

What did your boss say? What was the reply back?

[Jimmy]

So she actually said, we'll talk about this next week with a wink emoji.

[Brooke]

Hold on, hold on.

[Jeffrey]

Is she, like, one of those old people that don't understand how emojis.

[Jose]

Yeah, because my mom would have sent, like, red lips or something.

[Jeffrey]

Yeah, the sensual lips get sent by my mom, too. And I'm like, that's not.

[Brooke]

Maybe she got, like, squinty stern emoji with that one. Could that be it, what you're thinking?

[Jimmy]

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 as I feel about her.

[Brooke]

Dude.

[Jose]

And you've never even, like, thought about your boss like that?

[Jeffrey]

I love that a manager sets a meeting to tell you that she has.

[Brooke]

To say that you have a whole PowerPoint presentation ready to share her feelings back to you, dude.

[Jeffrey]

So embarrassing for her.

[Jimmy]

And now you guys know why I need your help.

[Jeffrey]

So you're telling us in where she's confessing that she feels the same way you don't say anything.

[Jimmy]

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 all's help on this one.

[Jeffrey]

Oh, my God.

[Brooke]

Okay. My God. So one thing.

[Jose]

You got me on your team, and I'm really good at ruining everything with women. So I'm gonna get on this, brother.

[Brooke]

All right.

[Jeffrey]

A couple of jokes from Jose be turned off.

[Jose]

Let me try to hit on her, actually. She'll really run away.

[Brooke]

Thanks to Jose, we might have some hope because we're going to call your boss and let you talk to her.

[Jeffrey]

Oh, my God.

[Brooke]

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.

[Jeffrey]

At least you didn't text your crush, though. Yeah, you know, really? I think that would have been better. Still happy about it?

[Brooke]

We'll let you make your awkward Tuesday phone call to your boss right after this. It's awkward.

[Jeffrey]

It's Tuesday.

[Brooke]

It's awkward Tuesday phone call. We don't have an HR department here anymore.

[Jeffrey]

I only laugh because it's true.

[Brooke]

But even with zero repercussions for our actions, we still know not to say I love you to our boss.

[Jeffrey]

Although our boss does have a really cute southern accent.

[Brooke]

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. 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?

[Jimmy]

It's Veronica.

[Brooke]

Veronica. Okay, so we're gonna 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?

[Jose]

You need to tell her that when you text her the other night, you didn't think twice about 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.

[Jeffrey]

It's not always illegal to date someone within the company. You could just need to go tell management.

[Jose]

Look, it's an easy out.

[Jeffrey]

Listen, have HR probably, yeah.

[Jose]

But no, just say, look, I think the logistics aren't going to work, and we got to separate and just stay where we are.

[Brooke]

Okay, You. You don't. You're not telling Her. That message wasn't for you.

[Jose]

No, because you don't want to let her down and make her feel bad. You just want to say, you know what? It's just not meant to be right now.

[Brooke]

Okay. Okay. Lightly stepping away. Brooke, what do you think?

[Jeffrey]

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. Because that ship has sailed, my friend. It is gone. It is left. 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.

[Jose]

I love that.

[Jeffrey]

You need to tell her. Tell her you have a secret family. What? Party with someone and he forgot to.

[Brooke]

Tell her he still has to work with her, though. She's going to lose all respect for him.

[Jeffrey]

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. It's a pretty good idea.

[Brooke]

Jimmy, how do you feel about those pieces of advice? Are you leaning towards either one?

[Jimmy]

I mean, I guess if I had to choose, I'd probably go with the Jose one.

[Jeffrey]

Yeah.

[Jose]

I win again, Brooke.

[Jeffrey]

Take that. I'm gonna tell you right now, she's gonna quit her job. You're gonna be honeymooning in the Bahamas.

[Jose]

Oh, I didn't think of that.

[Jeffrey]

Okay, go for it. Let's see how this works.

[Brooke]

Oh, no. I love how Brooke Des. Honeymooning in the Bahamas is a bad thing.

[Jeffrey]

It is a bad thing, Jeff.

[Brooke]

Well, I don't know. That's could be sounding kind of nice, but that was funny. We're gonna step away here, Jimmy. We're gonna dial your boss, Veronica for you and let you make your awkward Tuesday phone call. Good luck. Okay, we'll jump in if you feel like you need a little help. Here we go.

[Jeffrey]

Hello?

[Jimmy]

Hey, Veronica, it's Jimmy.

[Veronica]

Oh, Jimmy. You know what? Speak of the devil. I was just talking about you.

[Jimmy]

Hopefully good things.

[Veronica]

Oh, of course. All good things. By the way, the 9 o'clock meeting tomorrow is moved to 10:30. I want to make sure you got that memo, because I want to see you there.

[Jimmy]

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.

[Veronica]

I never said we were hooking up at the meeting, sweetheart. But maybe after.

[Jimmy]

Sorry, sorry. I did not mean a hook up at the meeting. Look, anyway, let me tell you why we need to talk. Oh, good. You know the text that I sent late Saturday night?

[Veronica]

I do know the text.

[Jimmy]

Honestly, I don't think I thought the whole thing through.

[Veronica]

What do you mean you didn't think it through? You are attracted to me, right?

[Jimmy]

Well, yeah, of course I'm attracted to you. I mean, how could anybody not be attracted to you? But you.

[Veronica]

You just needed a little liquid courage. You had that with your alcohol and it kind of opened up your. Your mind. And you don't have to worry. We can keep this 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.

[Jimmy]

Did you say boy toy?

[Veronica]

Oh, it's just a term of endearment. Don't worry.

[Jimmy]

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.

[Veronica]

Oh, I don't think that you're thinking this whole thing through. You wouldn't be my first experience at the office, sweetie.

[Jimmy]

Oh, my goodness.

[Veronica]

I probably shouldn't be telling this to you, but you know Luke and marketing?

[Jimmy]

Yeah, I know Luke. What about them?

[Veronica]

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.

[Brooke]

I can't.

[Jeffrey]

You can't. We all can't.

[Veronica]

What is going on?

[Brooke]

Hey, Veronica, you're on the radio right now with a show called Brooke and Jeffrey in the Morning.

[Veronica]

I'm on the radio?

[Brooke]

Yeah, yeah. Jimmy is one of our listeners and he asked for help doing this thing called the awkward Tuesday phone call.

[Jeffrey]

It sounds like you have a history of.

[Brooke]

Yeah. Is there any job openings where you work?

[Jeffrey]

Yeah. Do a lot of people work?

[Brooke]

Sounds actually like more fun than where we were.

[Jeffrey]

No, you guys, you shouldn't be doing this.

[Jimmy]

Guys, look, Veronica is awesome. Do not give her her hard time at all, please.

[Brooke]

No, we're not.

[Jimmy]

I'm.

[Brooke]

I'm complimenting her. If anything.

[Veronica]

I think that's Jimmy's job.

[Jeffrey]

What?

[Veronica]

To give me a hard time?

[Brooke]

Oh, Veronica, this is not the reaction that I was expecting at all. I thought she'd be upse upset or disappointed, but if any embarrassed For God's sake, if anything, she sounds turned on. I mean, Jimmy, this isn't really what you were going for, was it?

[Jimmy]

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'd been drinking too much. And that's where this all started, huh?

[Brooke]

Yeah.

[Jeffrey]

Do you. I mean, yeah, that's a lot.

[Brooke]

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.

[Jimmy]

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.

[Jeffrey]

Guess what, Jimmy? It was free, okay? You didn't pay for it.

[Veronica]

All right, well, Jimmy, I don't know what kind of advice they gave you, but that doesn't mean we can't hang out every once in a while. You know what I mean?

[Jeffrey]

Okay, Veronica, you need to. You can't do that.

[Veronica]

Why? He's already thinking the name Veronica in bed.

[Jimmy]

So?

[Veronica]

Why not?

[Brooke]

Did he mention that he also has a second family that he abandoned overseas?

[Veronica]

It's too late. We're hanging out.

[Brooke]

Wow.

[Jeffrey]

I think you need to. I mean, Jimmy, I think you need to get your resume together.

[Jimmy]

I mean, I guess. I don't know.

[Brooke]

It sounds like you're gonna get a promotion at this job. I don't know about that.

[Jimmy]

Look, all I want to do is. I just want this to.

[Veronica]

Please.

[Jimmy]

Please, let's 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.

[Veronica]

Okay, well, does that mean you were not undressing me? Because I was undressing you when I used to look at you.

[Jeffrey]

Lawsuit waiting to happen.

[Veronica]

I'm asking, Jimmy. I'm not asking you. Female Radio. Personal. Funny.

[Brooke]

Wow. She has had enough of you, Brooke.

[Jeffrey]

Yeah.

[Brooke]

Something is so antiquated. This is the modern working world.

[Jeffrey]

Okay, listen, if our office had an HR department, I would get that woman or person in here right now.

[Brooke]

Oh, it's a woman.

[Jeffrey]

No, we don't, bro.

[Brooke]

What a narc.

[Veronica]

Listen, sweetheart, that's my man. And I think you need to back up man.

[Brooke]

Now. Right. Well, this is terrible, Jimmy. It sounds like your boss isn't going to give you much of a choice here. I mean, I guess you've got two special ladies in your life now. A work wife and an out of work.

[Jeffrey]

Yeah.

[Brooke]

Make it easy on you.

[Jimmy]

Whatever. Okay.

[Brooke]

Look at Jeffrey in the morning.

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