Brooke and Jeffrey: Second Date Update - Awkward Tuesday: Never Hire Friends

Episode Date: September 16, 2025

One of our listeners THOUGHT she was doing the right thing lying to her boss and her company to get her friend hired, and in today’s Awkward Tuesday Phone Call we’ll find out how it turned into the worst decision she ever made!See omnystudio.com/listener for privacy information.

Hi, my name is Enya Umanzor. And I'm Drew Phillips. And we run a podcast called Emergency Intercom. If you're a crime junkie and you love crimes, we're not the podcast for you. But if you have unmedicated ADHD... Oh my God, perfect. And want to hear people with mental illness, psycho babble. Yes, yes.

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Visit apple.co-forward slash Reese Apple Books to find out more. Hey, welcome to your brand new second date podcast. Thanks for being here. It's Brook and Jeffrey in the morning. And yesterday, I love when people dive into our comment section and tell us how they feel about the episode. It's always fun to read.

Yeah, yesterday's hit a lot of strings. Yeah. Is that the right word for it? The right analogy, strings? We're never correct with sayings here anyways. We make up our own. All right. So, okay, if you didn't hear yesterday's episode,

go back and listen to it. There was a lot of anger at the end. It was a big miscommunication over who gave this woman flowers. And it turned out it was the gym worker. Yeah, who lied and then assumed, yeah, we had mixed reviews. One person said I work at a gym and I understand that you are categorized as just a gym employee. Someone else said, I was hoping for a 50 shades kind of story. Oh, okay.

With the rich guy on the treadmill. Yeah, I think so. Oh, wow, he's like, I own this. Yeah. Come into my helicopter and we'll fly away. We need more men like Mitchell, brave, courageous and ready to chase a woman down in a parking lot. True love is one parking lot surprise away. Okay, read that again.

To then, which someone replied and said, LOL, Brave, he lied, stood her up, hung up on her on the show. He had to catfish. Nobody wants a guy like this. Okay, you know, all over the place. You'd chase a girl down in a parking lot. That's what I was like, okay, this isn't very. Hopefully in the daylight makes it better.

Yeah, I guess it's all in. And don't grab her from behind. You know, that too. Make sure you figuratively grab her heart for her attention. Chase her with your mind. Yes. So anyways, I look. reading those though thanks guys hopefully we'll get some more comments about how you feel about

today's awkward Tuesday because it's brand new and it starts right now having a best friend is a real blessing oh yeah to have someone who would do anything for you they lend you money they'll let you crash on their couch for if not free a really small sum they'll be brutally honest about how that outfit you're wearing really looks on you. As they should be. Someone needs to be. Right?

Because they've got your back. And that's why our listener thought she was doing the right thing when she lied to her boss and to her entire company to help her best friend get hired. Oh, that's a big lie. Well, now in retrospect, it may have been the worst decision that she

has ever made. You're going to understand why she had no choice but to reach out to us in your brand new Awkward Tuesday phone call next. It's awkward It's Tuesday It's awkward Tuesday phone call There's a lot of sayings

That warn people about how you shouldn't date People that you work with Office romances never end well Sayings that Brooke has completely ignored Over the years Which is why all of our promo guys At our radio station never seemed to last It's all girls now actually

It is all girls They should be you know available as well Oh, I don't know. I'm kidding. I really don't think it's that big of a deal. We could tell. I mean, they do. As long as it's not like a weird boss, like, situation.

But I am curious, are there any warnings about don't hire your friends to work with you at your company? Oh, yeah. Friends and business don't mix. That is literally the same. Well, somebody didn't know about that saying, Brooke. Because one of our listeners, Kristen, emailed saying she got one of her friends hired at her work. Now she has to make an awkward Tuesday phone call about it. That's actually where I draw the line.

I don't do friends and business stuff. It ruins friendships every time. It's either humping or nothing. That's right. So, Kristen, welcome to the show. Hey, thanks for having me. Oh, goodness. So, wait, you're the one that got your friend the job?

Yeah, tell us the story. So I have actually been at the same company for seven years. And, I mean, it's the longest job I ever had. Things are going really well. I love it. Is that a sign if you can keep a job that long? Right, yeah, I'm doing something right, I think. Yeah.

But then, out of nowhere, I had an assistant quit, and she was great, very solid and dependable. It was just like a life choice change, nothing. Oh, no. Super dramatic or anything. The thought of one of my assistants quitting would just be. I mean, if I hooked up with them first, then that's okay, but just quitting out of the blue? No, it's one thing to get a friend a job for, like, somebody else in the company, a different apartment. Are you saying you got your friend an assistant job and you're the boss?

Oh, Brooke. Yes. This happens and I'm like out to happy hour with my best friend, Matt. And I tell him about it and like it gets so enthusiastic, freaks out. And he's like, oh my God, you have to pick me. I would be a great assistant. No. No, Matt would be a terrible assistant because you're best friends.

Yeah. I mean, honestly, like he may be a great assistant to anyone else. Yeah. But he just thinks like, oh, my God. We'd just be hanging out all day. It would be great. Yeah, yeah. I wish you guys were at the happy hour that day.

That would have helped my brain a little bit. Oh, no. That's okay. I was thinking the same thing. Like, I don't know about this. Yeah, hesitation before you went through with it. But what happened? Totally, totally.

And so he's like really pleading for me to give him a chance. So against my better judgment and that little voice in my head that apparently is all of you, but you weren't there. I did I hired him Oh my gosh What's happened since you hired him Well the most important thing was that when I hired him It was under one situation and it was that no one at the company

Could know that we were friends Oh Because that would look bad right Yeah and like I don't need anyone to know that I don't need to bring my personal life in But we pretend to like not know each other And the plan was that he could work there with me for a few months just as a way to get his foot in the door

and then he could apply to another position within the company and that would be good for him and then good for me and just like in the in between. So there was an end date to you being his boss. Yeah. Yeah, we could have a few fun months but that was three years ago and he's

still my assistant. How's the friendship? I bet it's great. Yo, it is horrible. Oh no. Who hates who more. I mean, it's not that we hate each other. It's just like he's taken advantage of this situation. That's the problem. Like, he's gotten into the pattern of skipping meetings or taking long lunches or forgetting to do like little tasks, like not huge things that would get

fired, but just like little things here and there. And it's just, it's not great. And I have been hinting at him for months to move on. I send him emails for applications and he just won't do it. He has like no initiative. And I'm like, did I make this too comfortable? Well, he's not getting reprimanded for anything. It sounds like a sweet job. He's taking a long luncheon. He's skipping what he wants to. Yeah.

Yeah. You mean, at this point, you sound like you're completely frustrated like you've totally had it with your friend. I mean, yeah, it's driving crazy. I can't work with him anymore. And I guess I'm at the point where I need help delivering the message, like very loud, very clear. It's time for you to move on without hurting our friendship because I do love him. And he still is my best friend. but with also not being his boss anymore.

Okay, so you're going to talk to him as his best friend, not as his boss. I think so. I think that's the idea because I don't want to fire him. I guess that would be the boss conversation, would be that. Would he care if he got fired? Like, does he? I hope so. Get unemployment if you get fired.

Okay. I just say it sounds like it's checked out, but you're right. I mean, still, that's all of his benefits. I'm sure he loves, like, collecting this paycheck of this nice, cushy job that he has and not having to work very much. for all that money, but how do you politely deliver that message? That's on us, and I'm afraid of what Brooke is going to say. I'm a little more direct than you are, Jeffrey.

That's what I'm saying. And I think that needs... I don't know if there's a way for Brooke to kindly tell a man you're not good enough right now. How do you be direct without being mean? And she's obviously been hinting for a long time, and the hinting isn't working. Like, it's better for him. It's better for her. It's better for everybody.

I cannot wait to see what that advice looks like coming from you, Brooke. I am dying to hear what we have to say to help you politely tell your friend slash assistant that he needs to move on from his job. I'm a guest looking forward to it too. I just want to

get past it. We all are. When we come back, give you your advice, and let you make your awkward Tuesday phone call coming up right after this. It's awkward. It's Tuesday. It's awkward Tuesday phone call. I may not know much

about my coworkers, but I know this. Nothing makes Brooks smile like the idea of a woman shaming her male counterpart telling him he's not doing good enough and needs to get his act together. What, tell me, tell me, what did I do wrong there? I do not shame male counterparts.

They just shame you. That is different. Okay. Totally different. And I also spent over a decade with you telling you how great you are. Not to my face. Yes, I've never heard that.

You are such a pain in my butt. And that's exactly what made one of our listeners email us for help. Our listener, Kristen, secretly got her friend Matt hired to be her new assistant. Of course, they didn't tell anyone at the company they knew each other because I was just supposed to be a way to get his foot in the door and then he could climb the company ladder. But three years later, Matt is still her assistant and seems to be taking advantage of their friendship because he's skipping meetings, missing tasks that he's supposed to be doing. So at this point, Kristen's finally had enough. She needs advice on how to politely but firmly tell him, time to saddle up, pony boy, or however corporate people talk. I don't think they say that.

Is that the email that you get? I'm sure. I don't really know. I think that's how the boss's email Jeff. So, Brooke, here's your moment. Tell Kristen how you would lay the hammer down on your mail counterpard. I don't think you have to lay the hammer down. Like, this is your best friend.

Like, a best friend is so important. And that's what you want to keep at the end of this. So here, here's what you do. You say to him, Matt, you deserve more money. Everybody wants more money. And I'm sure Matt wants more money. Am I right? I would assume so.

Everybody does. Yes. And you're like, listen, I'm going to help you get more money. We are going to find you a better job in this company. And we are going to get you paid. We're going to get you what you deserve because then you're hyping them up and helping him move on. Yeah, I guess just making money the focus of it, maybe we'll help his ears perk up a bit.

I actually like you're looking out for his financial interest to distract from your trying to get rid of him. So, Jose, what's your advice? Well, there's a famous line that says, absence makes the heart grow fonder. So right now, you guys are just too close. Yeah, that's true. Tell him you miss missing him. Right? You miss those times where you went weeks without seeing him.

Oh, right now. That's going to make someone feel good. You just don't appreciate him because he's there every day. Help him get a new job, and then you guys can rekindle your best friendship. Kristen, what do you think? Yeah, we are around each other a lot, so maybe that would be good for both of us. And a little laughter, a little humor could help lighten the message of what we're really trying to say beneath the surface here, which is get the F out. So I feel like that was actually some pretty good advice we gave you.

You can do what you want with it, but I'm going to dial your assistant slash best friend. friend Matt's number. Hopefully this awkward Tuesday phone call goes smooth. He's on the job right now, right? He's on the clock. Yeah, here we go. Good luck. We'll jump in and feel like you need some help, but I'm dialing it right now. Hello? Hey, Matt. It's Kristen. Oh, hey, girl. He disappeared on me earlier. Yeah, I just had to step out for a second. Right. So, Who's phone are you calling you from? I can't tell you that right now.

I am your assistant. You know, if you remember, you do have to tell me things. Yes, I remember. No, I'm just, I'm dealing with, I'm just dealing with something. Do you want to spill some tea on something in the office? You know all ears. No, it's not about our coworkers. It's

Matt, it's actually about you and me. What? What about you and me? Wait, are you mad that I missed the budget meeting yesterday? I told you, I'm sorry, I forgot to tell you. I was just getting a haircut. I mean, yeah, that's a good example. But I, first of all, you know I love you as a friend, first and foremost, right?

Girl, I don't like the tone of your voice right now. I just want to remind me. you like rewind three years about our whole like work arrangements when you got here right yeah that was like decades ago we were we were literally baby it was three years ago but look this position was supposed to get your foot in the door and like honey you haven't moved on wait what are you what are you saying I'm saying you need to go out there you need to be making more money. Okay, I just can't hide it anymore from you.

I guess I should tell because I've been feeling a little guilty myself. And I'm actually in the final interviews for the director of business development. And, you know, I've been wanting to tell you, but I was, like, scared to tell you. And I'm like, does this have something to do with that? Like, did you find out? Wait. What are you talking? about? Oh, I knew you were going to probably be jealous because that position makes more money

than you and I just didn't know really got to go about, you know. Wait, what? Oh my God. Uh-oh. That's great news. Congratulations. It's good for him. Wait, what's that? What is going on? Hey, wait, I don't. Let me jump in first here, Kristen, because I need to tell Matt, hey, dude, you're on the radio right now. It's like a conference call. Yeah. What? I'm so confused. Am I getting a trip or something? What's going on?

Oh, no. I wish we could do those things. You really like to read into stuff deeply, don't you, Matt? But this is just a radio show called Brooke and Jeffrey in the morning, and this segment is called The Awkward Tuesday Phone Call. Okay, that's awkward. So, wait, did she know about my new job? No, that's not the message.

I don't think so, especially not the way that Kristen was reacting. Kristen, do you want to talk to him and tell him what you know? Thank you. Sorry, I'm like fuming. I don't really understand. Did you even apply for it? Like, how long have you known? I'm just very confused right now.

No, I literally was having lunch with your boss a couple of weeks ago, and he just started asking me more about my career. And, you know, the job opening, like, it just kind of came up naturally. And he was insisting on, you know. So the person who is my assistant is going to be, you're going to be my superior. That's what's happening right now. I mean, not like directly, but I'm going to be making more money than you. Let's not bring that up again.

Oh, but that's what you said you wanted for him, right? Kristen, for him to make more money. Oh, wait a minute. Okay. Yes. Hang on. Wow. Yeah, Brooke, what good advice.

Well, I mean, is this a job you wanted, Kristen? Were you going after this position? No, I hadn't gone after it because this hasn't even been listed yet. This was not public information. Okay. I am just like a bit confused now because I thought you knew about the job, but now it's just sounding like you're, I don't know, a bit jealous or something. Oh.

I'm not, I'm not jealous. Okay, so if you thought I knew about the job, why didn't you bring it up? Why would you keep that? He told me not to say anything. And he said specifically that it wasn't going to be posted. It was kind of like an internal thing. They were trying to make things smooth and easy. And then I kind of thought that's what this call was about when you were calling me.

like you had found out or something. But what were you even talking for? Oh. I was going to say, I was going to say a lot of things. I guess I was going to say you deserve more money, but I... Sounds like exactly what you wanted for your friend is now happening for your friend in an even better way than you could have ever imagined.

I mean, Kristen, and if we're being completely honest here, like, I just feel like it was starting to get a bit stale, like even our relationship, our friendship dynamic And I really just needed a place to grow. And I just feel like I wasn't really growing anymore with you as my boss. Well, that's not true. Apparently your hair was growing enough where you needed to get a haircut during the last meeting that was supposed to be at. But still, you had already known about this promotion before that.

I mean, I only missed like a handful of meetings probably in the last month. And they weren't really even important. So. Is that true? What meeting is? Yeah, put a bit of emails. Yeah. I mean, Kristen, I'm taking your silence as you're totally thrilled with how this call is going.

This is insane. Did we break, Kristen? And I think I'm just going to have to take the day. I love you all. You've been to help. But I'm shaking over here. Girl, you need to take the day. I mean, we have drinks to get and celebrate.

Oh, my God. I love Matt. Well, drink's on Matt this time since he can afford it. And if it wasn't for you, I wouldn't even be here right now. So you helped me into this point of my life, too. So I don't know why you're so fast. Uh-huh. It sounds like now your friendship is going to be back in a better place now that

Matt's going to be moving on and up the company ladder. And Kristen, you sound totally happy with where you are. So that's awesome. You guys are funny. You guys are really funny. Brooke and Jeffrey in the morning. Hi, my name is Enya Emanzor. And I'm Drew Phillips.

And we run a podcast called Emergency Intercom. If you're a crime junkie and you love crimes, we're not the podcast for you. But if you have unmedicated ADHD... Oh my God, perfect. And want to hear people with mental illness, psychobabble. Yes, yes. Then Emergency Intercom is the podcast for you. Open your free IHeartRadio app.

Search Emergency Intercom and listen now. Imagine that you're on an airplane and all of a sudden you hear this. Attention passengers. The pilot is having an emergency and we need someone, anyone to land this plane. Think you could do it? It turns out that nearly 50% of men think that they could land the plane with the help of air traffic control. And they're saying like, okay, pull this until this. Pull that, turn this.

It's just, I can do it my ice close. I'm Mani. I'm Noah. This is Devin. And on our new show, No Such Thing, we get to the bottom of questions like these. Join us as we talk to the leading expert on overconfidence. Those who lack expertise lack the expertise they need to recognize that they lack expertise. And then, as we try the whole thing out for real.

Wait, what? Oh, that's the run right. I'm looking at this thing. See? Listen to No Such Thing on the. iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. You know, Matt definitely seemed confused there, probably because he didn't get to fully understand the whole reason why Kristen was calling and needing help in this conversation.

It's probably for the best that we didn't get into the details of why. Us and the listeners got all the details, and he still doesn't understand. And I'm really hoping that she's upset at her boss and not at Matt. Like, I think once she processes everything. thing. I'm sure she'll be really happy for her best friend. Of course. I mean, he was her assistant for three whole years and it might take her another three years just to get over the sudden promotion out of the blue. But in the end, it sounds like they have a really tight bond and this will actually be a good thing for their friendship. Yes. I don't know if it'll be good for

her career. No. It would be good for their friendship for sure. It'll be great for Matt's career. Are you sure? Based on his work habits that we heard, I don't know if he's going to be able to handle that director job. I don't know. So far. I think that's the thing about. directors have you not noticed they don't care yeah they don't go to things or was she setting up pointless meetings because he was like I just like five of them yeah and I'm over here thriving everybody the company loves me it's a power move to skip stuff yeah so just remember if you want to get an awkward Tuesday phone call you can always do it emailing the show and you can hear all of our awkward Tuesdays our second dates our phone taps all of our show content wherever you get

your podcast all over the world and even in certain parts of deep space If you just serve where I know we're expanding just right past the ozone layer Yeah That's where we are Find it in Brooke and Jeffrey in the morning Hi my name is Enya Umanzor And I'm Drew Phillips And we run a podcast called Emergency Intercom

If you're a crime junkie and you love crimes We're not the podcast for you But if you have unmedicated ADHD Oh my God perfect And want to hear people with mental illness Psychobabble Yes Yes.

Then Emergency Intercom is the podcast for you. Open your free IHeartRadio app. Search Emergency Intercom and listen now. Hey, it's your favorite Jersey girl, Gia Judice. Welcome to Casual Chaos, where I share my story. This week, I'm sitting down with Vanderpump Rule Star, Shea Shea. I don't really talk to either of them, if I'm being honest. There will be an occasional text, one way or the other, from me to Ariana.

Maybe a happy birthday from Ariana to me. I think the last time I talked to Tom. It was like, congrats on America's Got Talent. This is a combo you don't want to miss. Listen to Casual Chaos on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. If a baby is giggling in the back seat, they're probably happy. If a baby is crying in the back seat, they're probably hungry. But if a baby is sleeping in the back seat, will you remember they're even there?

When you're distracted, stressed, or not usually the one who drives them, The chances of forgetting them in the back seat are much higher. It can happen to anyone. Parked cars get hot fast and can be deadly. So get in the habit of checking the back seat when you leave. The message from NHTSA and the ad council. From standout speeches to the shows and stars making all of the history, my podcast, the latest with Lauren the Rosa, has your full Emmys breakdown.

The wins, the surprises, the cultural impact, and what it really means for us. I'm a homeguard that knows a little bit about everything and everybody. Listen to the latest with Lauren the Rosa from the Black Effect Podcast Network on the IHeartRadio app. You can get it at Apple Podcast or wherever you listen to your podcast. Just like great shoes, great books take you places. Through unforgettable love stories and into conversations with characters you'll never forget. I think any good romance, it gives me this feeling of like butterflies. I'm Danielle Robeye, and this is bookmarked by Reese's Book Club,

the new podcast from Hello Sunshine and IHeart Podcasts, where we dive into the stories that shape us, on the page, and off. Each week, I'm joined by authors, celebs, book talk stars, and more for conversations that will make you laugh, cry, and add way too many books to your TBR pile. Listen to Bookmarked by Reese's Book Club on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Apple Books is the official audio book.

and ebook home for Reese's book club. Visit apple.co forward slash Reese Apple Books to find out more.