Chapter 1: What challenges arise when friends handle money together?
It's hard. I've had friendships fall apart over this kind of stuff. But if you don't have $1,500 to spend on somebody else's vacation, you don't have $1,500 to spend on someone else's vacation. I'm Rima Grace, and welcome to This is Uncomfortable. This week, we're talking about money and friendships. We're answering your questions, offering advice on how to navigate some tricky dynamics.
And for this one, it felt right to bring on two people who've been friends for a while, comedians Josh Gondelman and Alison Leiby. Josh is a writer and stand-up comedian. Josh, welcome to the show. Thank you so much. It's so nice to be here with you, Rima, and I'm excited to ruin a friendship by talking about money. Let's do it. All right, Allison Leiby is also a stand-up.
Chapter 2: How do friendships change when financial expectations differ?
She was also a writer for shows like Broad City and The Marvelous Mrs. Maisel. Allison, welcome to the show. I'm so happy to be here. Well, I want to hear about your friendship. How did y'all become friends? We, I think, I don't know. I feel like in my life, I just like there are people that have just been in my life for a decade plus.
And I think the answer is probably just like small shows and open mics in New York, like very soon after I moved here, which was 2011. It's so funny in stand-up, there are, like, people for whom I have, like, a very distinct memory of, like, this is when we met and this is when our, like, friendship began.
And then there's people, which I think our friendship falls under for me, where I'm just like, I don't know, one day you were just, like, in my life a lot. Yeah, totally. Yeah. For sure. In a good way. Good way. Complimentary. Yeah, yeah. We just went two weeks. I was on the road and we went two weeks without hanging out, which is long for us.
And we like didn't know how to catch each other up on like two weeks. But also we talk all day every day. So there's also no gap in information. But then it's like.
we're keeping gchat alive we live close by we're yeah we're neighbors friends we we spent the last year working on like a writing project that required us to meet up in person like probably one to two times a week yeah okay so y'all are close so i'm curious has money ever caused any tension between you two maybe any awkward moments No. This is when I find out Josh is like, actually, yes.
I have a running tab.
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Chapter 3: What are the dynamics of splitting bills among friends?
We've been very lucky in our – just in our friendship that I feel like we've been ups and downs financially around the same times. So it feels nice that like you don't have to explain like, oh, I haven't like worked in a while. So maybe we just get beers at the dive bar and not like a fancy thing or whatever. Yeah. Right.
It's never come up for one of us is like, hey, I'm doing I'm doing a birthday party on the moon. Would you like to come? We're taking Blue Origin to the moon for my birthday. There'd be a lot of reasons that we would have to stop being friends because of that. Yeah, totally. It wouldn't just be financial. Yeah, it's because I'd be too cool. Way too cool. Moon guy. Moon guy.
Well, I'm really excited to see how y'all answer some of these questions from our listeners. They're pretty juicy. And our producer, Alice Wilder, is going to read them for us. Hello, Alice. Hi, Rima. Hi, Allison. Hi, Josh. Hi, Alice. So here's our first question. A few years ago, I started hanging out with a new friend group. They're all a bit younger than me.
I'm in my mid-30s and they're around 30. I'd say we're all solidly middle class, employed, prudent, and comfortable enough to spend on dinners out, weekend getaways, and other little treats. But I've noticed that I'll get Venmo requests from them for small things like a latte or my portion of a shared dessert. I'm used to more of a today for you, tomorrow for me style.
If I cover my friend's coffee, I assume at some point they'll put my cocktail on their tab and so on. Of course, for bigger expenses like concert tickets, I promptly pay my share. But I guess I'm wondering if this is an age thing, a trait of this particular group, or if I'm the one who's out of touch. Signed, new to the friend group. Hmm. All right. What do you all think of this?
It feels like it might just be, like, how this group, especially if, like, she's new to a group that, like, is doing this. That's just the culture of the group. That, like, I think you have to kind of just be like, this is how they do things. I'm new. Like, maybe over time it's also something that, like, as you're more ingratiated, it will ease up.
It feels like the kind of thing where you might have to just roll with this style for a bit. And, like, if it becomes... you know, unwieldy to be on Venmo that much, then maybe it's like, like a conversation. We're so addicted to our phones. I know. It's just like, I can't stop Venmoing. Bank of America. Zelle.
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Chapter 4: How can friends navigate uncomfortable money conversations?
That like, maybe then it's like a chill conversation of like, oh, hey, like I totally don't mind like getting these coffees. Like you can just get me back. Like that's kind of how I, like, I think there can be like a chill conversation, but you might also just have to be like, this is how these people deal with their money. And I'm part of this group now.
Well, you also don't know, unless you talk about money openly in the friend group, you don't know what some people are quietly dealing with if they're barely making rent each month or trying to pay off student loans or whatever. And so maybe requesting and sending small payments, it's not only financially necessary for them in the moment, but also just might soothe their anxiety.
I know a lot of people who just need that financial math squared away. Yeah. Yeah, and I think it is the kind of behavior that makes more sense when someone either is not making very much money or has financial commitments. You know, maybe someone is helping a family member pay bills.
And so like, even though they are budgeting carefully to be able to do the weekends away that everyone else is doing, they don't have that buffer of like, you know, this $75 for buying cocktails for five people, that's gonna put a hurt on my monthly expenses in the way it doesn't seem like it would from the outside.
I also have friends who would actually get offended if you like send them the Venmo amount that is like to cover your share of things because they're like, no, this is not how our friendship works. Like I don't want to feel like we're nickel and diming each other. Yeah. I feel very just like if it is a stress for me, I will tell you. And otherwise, like it is not.
And I'm just like, I'm going to see you again. We're going to get more drinks. We're going to have another dinner. Like it's like a promise to the friendship that like we're still hanging. Yeah, that's a really sweet way of thinking about it. Okay, new to the friend group, there is nothing wrong with the way you handle shared expenses.
But it seems like this group you're a part of just has a different way of going about it. Or they could have some financial concerns that you're not privy to. So you could casually bring it up or start paying for others and hope they catch on. But it might be easiest to just go with the flow. All right, so this next question is juicy. I can see Allison shaking her head already.
What do y'all think? You're still shaking your head. This is a scourge on relationships. I hate what weddings have become. I feel very grateful to be well into my 40s and out of this world of financial obligation. But like, I... started saying no to a lot of things when my, when my friends were like in the phase where it was like, Oh, everyone's getting married in this like three year run.
Just like, you know, you get, you get a weekend, you get the wedding. Like I, if I can do the bachelorette, I will come. And if I, and if I can't like, you have to understand that this isn't my wedding. This is your wedding.
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Chapter 5: What should you do if your friend frequently sends Venmo requests?
Also, do you disagree with any of our takes on these friendship and money questions? Or do you have your own question about a sticky situation? Let us know. Give us a call and leave a voicemail at 347-RING-TIU. That's 347-746-4848. Welcome back to This is Uncomfortable. I'm Rima Grace. If you have an uncomfortable money story to share, we want to hear about it.
We're keeping the conversation going over on Instagram and TikTok at thisisuncomfortablepod. I'm here with comedians and friends, Alison Leiby and Josh Gondelman, answering your questions about money and friends. Producer Alice Wilder has our next question. Mm-mm. Oh, that's a way different lie than I was thinking about.
I was thinking lie, but I was thinking a slightly, a slightly more translucent lie. What lie were you thinking? I was thinking you just go like, you know, um, I'm going to like best of luck, but like, I don't have a lot of sway over there. So like, you know, I can't really, I can't really move the needle with a recommendation on something like this for them. Yeah. Yeah.
That's the kind of lie I'd feel comfortable. I don't, I would not feel comfortable. He's like, I did it. I did it. Hope you get it. Yeah. Because especially if they get it. That doesn't feel like a white lie. That just feels like a lie. That's a classic lie. Oh, I would love to hear what this person thinks is like a deep, deeply rooted unethical lie. Oh, man.
Because their spectrum is calibrated differently than mine. Yeah. Yeah. Yeah. How would you handle this situation? I would tell the lie that I already said. Yeah, I would tell that lie. I'd split the difference and tell that lie. Because I don't want to get into like, you deliver low quality work if ever. That's not my job to tell somebody. And it's not my problem.
If you don't make it your problem, then it's not your problem that your friend is a slob at work. I don't need all my friends to be diligent employees. No, I don't care. But I'm also not putting my own name on, you know, name and reputation on somebody else's work. Yeah, I think I would just kind of wish you like, come on, I know you've got some sway.
Like, would you would you go as far as saying like, yeah, I would love to help. But like, in the past, when I've connected you with people don't really follow through on what you promised. And that puts me in a tough position. God, yeah. It's like, do you want to have that conversation? Yeah. I know. I know.
It's such a tough conversation because it's like it is not something that has to be a part of the friendship. Right. You know what I mean? Like it is like they're opting into this thing or they're trying to opt you into this facet of your relationship where you no longer feel comfortable. And it's like a hard thing to – explain because you want to be a good friend to this person, right?
You want to help them out, but you also don't want to do it at the expense of your own
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Chapter 6: How do wedding expenses impact friendships?
Yeah, I think so, too. Yeah, I went earlier in my 20s, I would have, like, made sure that I didn't pay for it. But I think now because I have a little bit more disposable income, I'm less inclined to make a big fuss out of it. And I'll just pay part of the alcohol. And then it's like what we talked about earlier. And I know my friends are cognizant of that.
And then they'll pay a little bit more the next time when we're out. Totally. Especially if it's friends that you're going to – that you see that group of friends on. If you're at like a friend's birthday and people you don't know like that are also there are ordering expensive bottles of wine, it's like that is your problem and not mine. Yeah. Yeah.
But if it's like a group thing, I could see – you know, it also – it all depends. Like are we talking an extra $100? Are we talking an extra $25? Like those things matter. But like, yeah, like I would never – if somebody wasn't drinking and I was at a dinner where we're like ordering wine, I would never expect somebody to pay for that. Okay, this is our last one. Okay.
Your friend spilled his latte all over your laptop and it needs to be replaced. That's tough. Oh, God. I hate that. Oh, God. I don't know. As somebody who desperately needs to buy a new computer, I, like, you can't, like, also just, like, accidents happen. I've spilled liquids on my own computer and it's, like, it's terrible.
But, like, I feel like you can't ask somebody for, like, to buy it for you. But, like. You would hope that they would offer. You would hope they would offer. But also they might not be in the financial position. Right. Yeah. And also if they're not in the financial position to offer. Right. I don't want to extract that from them either. Right.
But I feel like this is the kind of thing that can actually fracture a friendship or like just end a friendship altogether. It reminds me of a friend in college who lent her car to some mutual friends and they got into an accident and totaled it. And the expectation was that they had to obviously pay for it.
But they were college students and it was this big saga and, you know, it completely ruined their friendship. That's really tough. With something like this, if they offered, I would accept a meaningful amount of help. And if they didn't offer, I think I would maybe ask for... Say, hey, I have to replace this. I was wondering if you could help me defray some of this cost.
Like, maybe figure out some portion of it that would be, like, helpful, but not, like, buy me a new computer. Right, yeah. And, like, not something that'll be a burden to them, but, like, a computer is an expensive piece of equipment that, like, you also need. It's not like... Oh no, I have to replace my fancy hat. You need to have it. You can't not have it.
So yeah, I think I would have to actually be like, if there's any way you can kick me a little cash, like this is also tough for me. And I don't know. And knowing that they might not. Yeah, totally. I think... it's also like to be thoughtful to whatever financial position there. And you go, I tried to, I took it to the place to see if they could restore the hard drive.
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