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Jeffrey
Hey, what's up?
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Brooke
Hey, welcome to your brand new Second Date podcast. Thanks for being here. It's Brooke 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.
Kristen
We're never correct with sayings here.
Brooke
Anyways, we make up our own, Right? So, okay, if you didn't hear yesterday's episode, go back and listen to it. There's 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.
Kristen
All right.
Brooke
Someone said, with a rich guy on the trail? Yeah, I think so. Wow.
Jeffrey
He's like, I own this chair.
Brooke
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.
Jeffrey
Okay, read that again.
Kristen
To thin.
Brooke
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.
Kristen
Okay.
Jeffrey
You know, you chase a girl down in a parking lot.
Brooke
That's what I was like.
Jeffrey
Okay, this isn't very.
Brooke
Hopefully in the daylight makes it better.
Jeffrey
Yeah, I mean, I guess it's all in.
Brooke
And don't grab her from behind.
Kristen
You know that too.
Brooke
Figuratively. Grab her heart for her attention.
Jeffrey
Chase her with your mind.
Brooke
Yes. So anyways, I loved 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.
Jeffrey
Having a best friend is a real blessing.
Announcer
Aw.
Brooke
Yeah, it is.
Jeffrey
To have someone who would do anything, 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.
Brooke
Yeah. As they should be. Someone needs to be.
Jeffrey
Yeah, right. Cuz 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.
Brooke
Oh, that's a real one.
Jeffrey
Well now, in retrospect, it may have been the worst decision that she has ever made.
Brooke
Oh, goodness.
Jeffrey
You're gonna understand why she had no choice but to reach out to us in your brand new awkward Tuesday phone call. Next. It's awkward.
Announcer
It's Tuesday.
Jeffrey
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. Oh, office romances never end well. Oh, yeah. Sayings that Brooke has completely ignored over the years. Which is why all of our promo guys at our radio station never seem to last. It's all girls now. Actually, it is all girls.
Brooke
They should be, you know, available as well.
Jeffrey
Oh, I don't know.
Brooke
I'm kidding. I really don't think it's that big of a deal.
Jeffrey
We could tell people meet up.
Brooke
I mean, they do. As long as it's not like a weird boss like situation. Yeah.
Jeffrey
I am curious. Are there any warnings about don't hire your friends to work with you at your company?
Brooke
Oh, yeah. Friends and business don't mix. That is literally the saying.
Jeffrey
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.
Brooke
That's actually where I draw the line. I don't do friends and business stuff, but it ruins friendships every time.
Jeffrey
Just, it's either humping or nothing.
Brooke
That's right.
Jeffrey
So, Kristen, welcome to the show.
Kristen
Hey, thanks for having me.
Brooke
Oh, goodness. So wait, you're the one that got your friend the job?
Jeffrey
Yeah. Tell us the story.
Kristen
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. Like, I love it if you can.
Jeffrey
Keep a job that long.
Kristen
Right? Yeah. Doing something right, I think.
Jeffrey
Yeah.
Kristen
But then out of nowhere, I had an assistant quit. And she. She was great. Very solid and dependable. It was just like a life choice change. Nothing super dramatic or anything.
Jeffrey
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.
Brooke
No, it's one thing to get a friend a job for, like, somebody else in the company. A different department. Are you saying you got your friend an assistant job and you're the boss?
Jeffrey
Oh, bro.
Kristen
Yeah. This happens, and I'm, like, out to happy hour with my best friend Matt, and I tell him about it, and, like, gets so enthusiastic, freaks out, and he's like, oh, my God, you have to pick me. I would be a great assistant.
Brooke
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.
Jeffrey
But he just thinks, like, oh, my God, we should be hanging out all day. This would be great.
Kristen
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.
Jeffrey
Yeah. Hesitation before you went through with it, but what happened?
Kristen
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. I did. I hired him.
Matt
Oh, my God.
Jeffrey
Oh. What's happened since you hired him?
Kristen
Well, the most important thing was that when I hired him, it was under one stipulation, and it was that no one at the company could know that we were friends. Oh.
Brooke
Because that would look bad, right?
Kristen
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, just like in the.
Brooke
So there was an end date to you being his boss?
Jeffrey
Yeah.
Kristen
Yeah. We could have a few fun months, but that was three years ago, and he's still my assistant.
Brooke
How's the friendship? I bet it's great.
Kristen
Yo, it is horrible.
Jeffrey
Oh, no.
Brooke
Who hates who more?
Kristen
I mean, it's not that we hate each other. It's just, like, he's taken advantage of the situation.
Matt
That's the problem.
Kristen
Like, he's gotten to the pattern of skipping meetings or taking long lunches or forgetting to do, like, little tasks. Like, not huge things that would get him 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?
Brooke
Well, he's not getting reprimanded for anything. It sounds like a sweet job. He's taking long lunches. He's skipping what he wants to.
Jeffrey
Yeah, you mean. At this point, you sound like you're completely frustrated. Like you've totally had it with your friend.
Kristen
I mean, yeah, it's driving crazy. I can't work with him anymore. And I just. 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.
Brooke
Okay, so you're gonna talk to him as his best friend, not as his boss?
Kristen
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.
Jeffrey
Would he care if he got fired? Like, does he?
Kristen
I hope so.
Brooke
Get unemployment if you get fired.
Jeffrey
Okay, I'm just going to sound like it's true now, 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.
Brooke
I'm a little more direct than you are.
Jeffrey
That's what I'm saying.
Brooke
And I think.
Jeffrey
I don't know if there's a way for Brooke to kindly tell a man you're not good enough right now.
Brooke
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.
Jeffrey
I cannot wait to see what that advice looks like coming from you. Oh, my God. 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.
Kristen
I'm a guest. Looking forward to it, too.
Matt
I just want to get, when we.
Jeffrey
Come back, give your advice and let you make your awkward Tuesday phone call. Coming up right after this. It's awkward.
Announcer
It's Tuesday.
Jeffrey
It's awkward. Tuesday. Phone call. I may not know much about my co workers, but I know this. Nothing makes Brooke 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?
Brooke
I do not shame male counterparts. I just shame you.
Matt
Okay.
Jeffrey
Yes, totally.
Brooke
And I also spent over a decade with you telling you how great you are.
Jeffrey
Not to my face.
Brooke
I've never heard that. You are such a pain in my butt.
Jeffrey
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.
Kristen
Yeah.
Jeffrey
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.
Brooke
I don't think they say that the.
Jeffrey
Email, I'm sure I don't really know.
Brooke
I think that's how the bosses email Jeff.
Jeffrey
So, Brooke, your moment. Tell Kristen how you would lay the hammer down on your male counterpart.
Brooke
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?
Kristen
I would assume so. Everybody does.
Jeffrey
Yeah.
Brooke
And you're like, listen, I'm going to help you get more money. We are going to find you a better job 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.
Kristen
Yeah. I guess just making money the focus of it maybe will help his ears perk up a bit.
Jeffrey
Yeah. 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.
Brooke
Yeah, that's true.
Jeffrey
Tell him you miss missing him, huh?
Matt
Right?
Jeffrey
You miss those times where you went weeks without seeing him right now.
Brooke
That's gonna make someone feel good.
Jeffrey
Yeah, 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. Kristin, what do you think?
Kristen
Yeah, we are around each other a lot, so maybe that would be good for both of us.
Jeffrey
And a little laughter, a little humor could help lighten the message of what we're really trying 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 sl. Best friend Matt's number. Hopefully this awkward Tuesday phone call go smooth. He's on the job right now, right? He's on the clock. Yeah. Here we go. Good luck. We'll jump in you feel like you need some help, and I'm dialing you right now.
Matt
Hello?
Kristen
Hey, Matt, it's Kristen.
Matt
Oh, hey, girl. You disappeared on me earlier.
Kristen
Yeah, I just had to step up for a second.
Matt
Right. So whose phone are you calling me from?
Kristen
I can't tell you that right now.
Matt
I am your assistant, you know, if you remember. You do have to tell me things.
Kristen
Yes, I remember. No, I'm just. I'm dealing with. I'm just dealing with something.
Matt
Do you want to spill some tea on something in the office? You know, I'm all ears.
Kristen
No, it's not about our co workers. It's. Matt, it's actually about you and me.
Matt
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. Oh.
Kristen
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?
Matt
Girl, I don't like the tone of your voice right now.
Kristen
I just want to remind you, like, rewind three years about our whole, like, work arrangement when you got here, right?
Matt
Yeah. That was, like, decades ago. We were literally babies.
Kristen
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.
Matt
Wait, what are you. What are you saying?
Kristen
I'm saying you need to go out there. You need to be making more money.
Matt
Okay? I. I just can't hide it anymore from you. I guess I should, 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. 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, or.
Kristen
Oh, wait, what? What are you talking about?
Matt
Oh, you knew you were gonna probably be jealous because that position makes more money than you, and I just didn't know really how to go about, you know.
Kristen
Wait, what? Awkward.
Jeffrey
Oh, my God.
Matt
Uh.
Brooke
Oh, that's great news. Yeah, congratulations.
Jeffrey
It's good for him.
Matt
Wait, what the. What is going on?
Kristen
I don't.
Jeffrey
Let me jump in first here, Kristen, because I need to tell Matt. Hey, dude, you're on the radio right now.
Brooke
Like a conference call?
Jeffrey
Yeah.
Matt
What? I'm so confused. Am I getting a trip or something? What's going on?
Brooke
I wish we could do those things.
Jeffrey
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.
Matt
Okay, that's awkward. So. So we. Did she know about my new job?
Brooke
No, that's not the best thing.
Jeffrey
I don't think so. Especially not the way that Kristin was reacting. Kristen, do you want to talk to him and tell him what you.
Kristen
Yeah, thank you. Sorry, I'm, like, fuming. I don't really understand. Did you even apply for it? Like, how long have. You know, I'm just very confused right now.
Matt
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 insistent on, you know.
Kristen
Who is my assistant is going to be. You're going to be my superior. That's what's happening right now.
Matt
I mean, not. Not, like, directly, but I'm gonna be making more money than you, so let's.
Brooke
Not bring that up again.
Jeffrey
Oh, but that's what you said you wanted for him, right, Kristin? For him to make more money. Oh, wait a minute.
Kristen
Okay. Yes. Hang on. Wow.
Jeffrey
Yeah. Brooke. What good advice.
Brooke
Well, I mean, is this a job you wanted, Kristen? Were you going after this position?
Kristen
No, I hadn't gone after it because this hasn't even been listed yet. This was not public information.
Matt
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.
Kristen
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?
Matt
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 going to call me for?
Kristen
Oh, I. I was gonna say. I was gonna say a lot of things. I guess I was gonna say you deserve more money, but I sounds like.
Jeffrey
Exactly what you wanted for your friend is now happen in an even better way than you could have ever imagined.
Matt
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, I really just needed a place to grow and I just feel like I wasn't really growing anymore with you as my boss.
Jeffrey
Well, that's not true. Apparently your hair was growing enough where you needed to get a haircut during the last meeting that you were supposed to be at. But still, you had already known about this promotion before that.
Matt
I mean, I only missed like a handful of meetings probably in the last month and they weren't really even important, so.
Brooke
Isn't that true? What meeting is.
Jeffrey
Yeah. Could have been an email. Yeah. So I mean, Kristen, I'm taking your silence as you're totally thrilled with how this call is going and this is insane.
Kristen
Did we break her Swayze? And I think I'm just gonna have to take the day. I love you all. You've been a help, but I' I'm shaking over here.
Matt
Oh no, girl, you need to take the day. I mean, we have drinks to get and celebrate and you know.
Kristen
I love Matt.
Brooke
Well, drink's on Matt this time since he can afford it.
Matt
And if it wasn't for you, I wouldn't even be here right now. So. You helped me into this point in my life too, so I don't know why you're so fast.
Kristen
Uh huh.
Jeffrey
All right, well it sounds like now your friendship is gon back in a better place now that Matt's gonna be moving on and up the company ladder. And Kristen, you sound totally happy with where you are, so. That's awesome.
Kristen
You guys are funny. You guys are really funny.
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Jeffrey
Hey, what's up?
Mario Lopez
It's Mario Lopez. Back to school is an exciting time, but it can also be overwhelming and kids may feel isolated, a vulnerability that human traffickers can exploit. Human trafficking doesn't always look like what you expect. Everyday moments can become opportunities for someone with bad intentions. Whether you're a parent, teacher, coach or neighbor. Check in, ask questions, stay connected. Blue Campaign is a national awareness initiative that provides resources to help recognize suspected instances of human trafficking. Learn the signs and how to report@dhs.gov blue campaign.
Jeffrey
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. The listeners got all the details and he still doesn't understand.
Brooke
And I'm really hoping that she's upset at her boss and not at Matt. Like I think once, yeah, once she processes everything, I'm sure she'll be really happy for her best friend.
Jeffrey
I mean, he was her assistant for for three whole years and it might take her another three years just to get over this 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.
Brooke
Yes. I don't know if it'll be good for her career, but it'll be good for their friendship. For sure it'll be great for Matt's career.
Jeffrey
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.
Brooke
I don't know. So far. I think that's the thing about directors. Have you not noticed this? They don't care. Yeah. They don't go to things.
Jeffrey
Or was she setting up pointless meetings because he was like, I just like five of them. Yeah. And I'm over here thriving. Yeah. Everybody at the company loves me.
Brooke
It's a power move to skip stuff.
Jeffrey
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 podcasts all over the world and even in certain parts of deep space. I know we're expanding just right past the ozone layer. Yeah. That's where we are. You find it at Brooke and Jeffrey in the Morning.
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Jeffrey
Hey, what's up?
Mario Lopez
It's Mario Lopez. Back to school is an exciting time, but it can also be overwhelming and kids may feel isolated, a vulnerability that human traffickers can exploit. Human trafficking doesn't always look like what you expect. Everyday moments can become opportunities for someone with bad intentions. Whether you're a parent, teacher, coach or neighbor. Check in, ask questions, stay connected. Blue Campaign is a national awareness initiative that provides resources to help recognize suspected instances of human trafficking. Learn the signs and how to report@dhs.gov.
Jeffrey
Blue Campaign Thursday night Football is on and it's only on Prime Video. Infinite Touchdown this Thursday in AFC east rivalry ignite at the Miami Dolphins battle the Buffalo Bills in a heated division showdown.
Kristen
Boom.
Matt
Right on the money.
Jeffrey
Coverage begins at 7pm Eastern with Football's Best Party TNF tonight presented by Verizon. Not a Prime member? Not a problem. Simply sign up for a 30 day free trial. Today it's the Dolphins and the bills. Thursday at 7pm Eastern only on Prime Video. Restrictions apply. See Amazon.com amazonprime for details.
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Matt
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Jeffrey
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Kristen
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Kristen
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Kristen
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Jeffrey
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Release Date: September 16, 2025
Host: Brooke & Jeffrey || Guests: Kristen, Matt
The central theme of this episode is the classic dilemma of mixing friendship and business. The listener, Kristen, finds herself deep in regret after pulling strings to hire her best friend Matt as her assistant. Three years later, the situation has devolved—Matt is underperforming and their friendship is suffering. Kristen seeks help from the Brooke & Jeffrey team to navigate a delicate, and very awkward, conversation: how to push her best friend to move on from his cushy, underwhelming role—without ruining the friendship.
The story unfolds in classic "Awkward Tuesday" fashion, culminating in a big twist that nobody saw coming.
Light, comedic, and full of the playful banter that typifies Brooke & Jeffrey’s style—even as they tackle the real anxieties and complications of life, work, and friendship.
This summary covers all major discussion points, pivotal exchanges, and the memorable, twist ending. Listen for candid, relatable confessions—and that signature Brooke & Jeffrey blend of heart and humor.