In the spring of 2023, Jay Benedith’s dating profile stopped Ben Williams in his tracks: a beautiful woman looking for someone “intellectually stimulating, sexually intimate, and silly”? He sent a like. When Jay reciprocated, they scheduled a video call for the next day. Several video calls and numerous dates later, they were dating dating.
Everything was going well until about a month into their relationship when Jay invited Ben on a trip to Panama, and they realized just how differently they approach money. Weeks before the trip, without warning, Jay sent Ben a Venmo request for his half of the Panama hotel. “It just rubbed me the wrong way,” Ben told us. “This is still like a month out, and she’s asking me for money?”
As their relationship got more serious, they realized their disagreement over Venmo requests goes much deeper.
“Being very careful with how I spend my money and how I’m earning money is, like, very built into my DNA,” Jay explained.
Jay and Ben share with host Reema Khrais how nickel-and-diming (and more importantly, miscommunication around money) can test a relationship.
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This Is Uncomfortable October 17, 2024 Transcript
Note: Marketplace podcasts are meant to be heard, with emphasis, tone and audio elements a transcript can’t capture. Transcripts are generated using a combination of automated software and human transcribers, and may contain errors. Please check the corresponding audio before quoting.
Reema Khrais: Meet Jay.
Jay Benedith: although everyone calls me Jay, my government name is Julia Benedith, and I am 32 years old.
Reema: She recently earned her doctorate degree, and she keeps her life meticulously organized.
Jay: I’m just like a bad b with everything handled.
Reema: But she was missing one thing: a partner who could match her energy. That’s where Ben comes in…
Ben Williams: I am Ben Williams. I am a high school history teacher in DC // I’m also very involved in local politics
Reema: On paper, they’re very different…
Jay: So I’m Afro Latina.
Ben: I’m white.
Jay: I’m Buddhist.
Ben: And I’m from a Jewish family.
Jay: I grew up in New York City and very much a city girl.
Ben: I grew up in the suburbs of Ohio.
Reema: But sometimes all it takes is a swipe to make a like..
Jay: He’s an educator, which was, like, super sexy.
Ben: She looked like a free spirit, and I was attracted to that.
Reema: Turn into love. And all it takes is a venmo… to throw it all into question.
Ben: We had been dating for like a month. So I was like, is she inviting me to like help her cover her costs?
Jay: If you’re just, like, willfully not paying your portion, I just think that that is, like, inequitable and also just rude.
Reema: They’re a match made in heaven– but will nickel and diming bring them crashing down to earth?
I’m Reema Khrais, you’re listening to This is Uncomfortable. This week, we have a modern romcom for you…and it’s also the latest installment in a series we do on this show called “Money Fight.” Where we get all in people’s business, learning what exactly went down in a conflict that involves money, but is about something much deeper.
Jay Benedith is a listener who wrote in to tell us about a disagreement she and her partner Ben Williams wrestled with early in their relationship. They had very different money habits that led to miscommunication, annoyance and some lingering venmo requests.
And I have to say–when I first started working on this episode I identified more with one person in the couple, and then ended up changing my mind a couple times. Even people on our team were divided.
Before we get to all of that though, I want to tell you about the early days of Jay and Ben’s relationship. It was the Spring of 2023, and Ben was swiping through profiles on Hinge, when he saw a beautiful woman with a profile that stopped him in his tracks.
Ben: there was one phrase that she said where she was looking for someone to be… like intellectually… I can’t remember exactly, but like essentially like –
Jay: intellectually stimulating, sexually intimate, and silly.
Reema: Jay was about to take a break from dating when she got that “like” from Ben. She was like, “I’ll give him a chance, but if this doesn’t work out? I’m off the apps.” But luckily…
Jay: it was pretty immediate, like it was like we matched and then like the very next day we were on video chat.
Reema: Oh wow!
Jay: And we talked for about an hour each time, I think.
Reemma: After a couple video calls, they had their first date– grabbing dinner at a Vietnamese restaurant in D.C., where they both live. And it was the first time money really came up.
Ben: Jay, do you, is it your memory that, like, we split the bill that first date?
Jay: I don’t know. You might have paid.
Ben: Yeah, I think I paid. Um…
Jay: But I was willing to pay.
Ben: You were! You did offer, which I appreciated
Reema: They couldn’t stay out too late– they both had work the next morning, but they had a good time and left eager to meet up again.
Ben: you were pretty upfront from the beginning, maybe like the second or third date that like you wanted something serious.
Jay: Yeah.
Reema: How did you respond to that, Ben?
Ben: I was like, oh no, no. [laughter]
Jay: [jokingly] stop!
Reema: Ben had just gotten out of a situationship and was looking to casually date but also…
Ben: I think our conversation was just like so natural and that I was willing to kind of give things a shot.
Reema: Pretty soon they were dating dating. They started doing all those new couple things, like showing each other their favorite shows. Jay loves Insecure, which Ben had never seen.
Jay: I just thought that was unacceptable.
Reema: Right.
Jay: So we watched it together and then I hadn’t seen The Wire. He thought that was unacceptable. And he low key likes reality TV.
Reema: Oh that’s fun.
Jay: Like, I’ll watch “90 Day Fiancé” and like, he’ll pretend, like, he’s not interested, but he is.
Reema: They were going for romantic walks along the Potomac River. Jay helped Ben grade tests for his class. She was a teacher for eight years before pursuing her doctorate in education. And Ben helped Jay, a city girl, become a more confident driver. I could keep going, it’s all very cute.
Things were going so well that just one month into the relationship Jay invited Ben to join her on a trip to Panama.
Reema: That’s a big deal. Were you nervous about how it would go?
Ben: I was nervous! I was excited too but I was just like, I mean, it was a great test for, for the relationship. I mean, it was like, you know, I told my friends I loved them in case, you know, she was a serial killer and I didn’t come back. [laugh]
Reema: Don’t worry– this is not a true crime podcast.
Ben: But, but also I was like, if we can, if we travel well together, like this is a great sign. And if it doesn’t go well, I’m at least back in the States in three days.
Reema: Before their romantic trip, they had to take care of some logistics– booking flights, figuring out accommodations. Ben was at work in the classroom when he got a Venmo request for two hundred and seventy dollars and seventy cents.
Ben: It just came up o n my phone. Like it, I think in the past relationships um, we’ll often talk about, you know, how we’re going to pay for things, and then send the request.
Reema: Getting this out of nowhere – like not even getting a text saying hey sent you a venmo request! – it made Ben nervous
Ben: At that time we had been dating for like a month, So I was like, is she inviting me to like help her cover her costs?
Reema: But to Jay, sending this request was totally routine.
Jay: So before we went on the trip, like, I venmo’d him for half of the hotel. It was just like a very practical thing, like I’m going through my budget and you know, just wanted to get that out of the way. And Ben did not pay me, um, immediately. Initially I was just like, okay like maybe he just hasn’t gotten to it…
Reema: But then days passed and with the trip approaching…
Jay: I was like, okay like what’s happening? like Did he not see the request? Do I need to send him a reminder?
Reema: When those two different perspectives came up against each other…
Ben: It definitely led to some, um, I don’t know, would you say conflict, babe?
Jay: I, we definitely talked about it and like, I could see where you’re coming from, you know…
Reema: How did it come up?
Jay: I think pretty like directly. I think Ben was like, Hey, like, can we talk about, you know, Venmo requests before they are sent?
Reema: But there was still the matter of this venmo request. And the bigger questions it brought up for them.
Ben: I was like, is this going to work? Like, can I, can I be with someone who’s so I used the word rigid at the very, at the beginning and she didn’t like hearing that.
Jay: I also have been told by previous partners that like, I can be rigid or like, just very in my ways. Um, that being said, I didn’t understand how it applied to this situation necessarily. I didn’t think I was being rigid; I think I was just being practical. He was gonna have to pay me for half anyway, so I just didn’t see why it would be an issue to, like, pay me when I sent the request.
Reema: Meanwhile the request for Panama was still sitting there, still unpaid. And the trip was getting closer.
Jay: What is going on? Like, why is he not paying me? Am I missing something here?
Reema: How long did it sit there for?
Ben: It had been some time. I was stall- I was stalling. [laugh[
Reema: Oh, really?
Ben: I think it was like my way of like protesting! I don’t think that, like, in hindsight I was maybe as conscious of it as I’m making myself out to be right now. Um, but I, it just rubbed me the wrong way. It was like, this hasn’t happened, this is still like a month out, uh, and she’s just asking me for money.
Reema: Okay so, not a great start to their first trip as a couple. But once they got to Panama, it was pretty magical. They visited an island with a view of the Panama Canal, and ate incredible food. Ben initiated a conversation about how they’d handle expenses while traveling– he was like, “Can we focus on connecting and having fun and settle up expenses when we get home?” Jay agreed.
Ben: It gave me a little faith that she was willing to be flexible.
Reema: Meanwhile, the trip sparked something for Jay. Maybe it was the tropical breezes, or seeing Ben’s sunkissed skin…
Ben: I remember when we were in Panama City, she turned over and, um, one morning, like, said that I love you, and, and I was just like, didn’t say anything.
[Nervous laughter]
Reema: What, what was going through your head?
Ben: Um…. I was like, I mean, I was really touched and I was flattered. I didn’t know if it was like, how wonderful the vacation was going or if like, she felt it. And I think the beautiful thing about being with Jay is like, we’re both um, you know, really true to ourselves. So, she also said like, “Hey, you don’t have to say this back. I just want you to know that I feel this.” And, I just felt really touched.
Jay: I could just feel like. In my body that I was, there was so much love for Ben, and um I just wanted him to know that I was feeling something real for him.
Reema: Back in D.C., they felt more excited than ever about their relationship. Ben had some confidence that Jay could be flexible. And Jay was in love! With a man who no longer owed her money– he’d finally paid for his half of the hotel!
A few weeks later, they were on another trip, this time to the outer banks of North Carolina. One evening they were sitting on the sand and looking at the stars. As the crabs scurried across their feet, Ben told Jay that he loved her too.
And Ben started to understand that the money stuff wasn’t personal. Jay is extremely diligent with every part of her life.
Ben: Jay, she has a Google doc called It’s Handled, and there’s many things in that where she is organized to a T on her monthly expenses, her organization with clothes, her passwords, and a couple other things.
Reema: Wow, what? I want to hear about this.
Jay: So it starts off with my calendar for the week. Like I’ll just like quickly put in like what I’m doing. Um, every day it also has the weather so I don’t have to like look at the weather app. It’s just like right there, and then it goes into like the different like buckets of my life. So the last bucket is my budget and like I, like before I even leave the supermarket, like I’ll quickly look at the receipt and I’ll like plug in how much I spent, um, on food and like in that line item in my budget. Um, so yeah, I, I try to be like very meticulous, because, you know, as they say, like if you stay ready, you never have to get ready.
Reema: First of all, I am so impressed by this system. And second– it helps me get why an unpaid venmo might be a problem for her.
Jay: Just seeing the Venmo request unfulfilled was just, like, Ah, like, there’s this thing that’s, like, in the balance, and, like, I just wanna, like, check it off the list, um, So, it, it makes me feel, like, Maybe a little anxious, um, but I feel like that’s too strong of a word. But I think annoyed is also not quite the word. But it’s like something in the middle.
Reema: Yeah, it’s like, you’re a little unsettled. Like, pun
Jay: Yeah.
Reema: Pun intended I guess.
Reema: When Ben first saw her spreadsheet he was a little intimidated.
Ben: I was just like, Oh, you know, like, am I, am I not doing well enough? Like, I don’t have this, you know, um, like it just made me a little like self conscious initially with thinking about like my, um, or my habits.
Reema: And for Ben, that level of organization can also feel like control. Like, growing up his mom would tell him:
Ben: You know, you want to be with a spouse that’s gonna allow you to like be yourself and like you don’t want to if you put your shoes in the wrong place like you don’t want to get, you know, snapped at. I always like a respectful communicator, but there were times where I would like put my bag somewhere in her house and then like, I would wake up and it’d be in a totally different spot…
[Jay laughing]
Ben: …uh, or I’d put my shoes by the couch and then I’m like, where are my shoes?
Reema: It’s a pretty common feeling to have in a new relationship: excitement about this new person in your life… and some reservations about what life together will look like. But for Jay and Ben, the excitement outweighed the concern. And then…
Reema: I’ve heard about the seltzer incident, um, can you all tell me about that? What happened?
[Laughter and groans from Jay and Ben]
Ben: Jay, you want me to take this one?
Jay: Yeah.. [laughter]
Reema: After the break…the seltzer incident.
[AD BREAK]
Reema: And we’re back.
Ben: Jay was coming from her place and, um, I have a grill at my place. It was Friday night, and I was cooking us dinner. And, um, mostly what we say is like that we’ll split, um, bills when we go out to dinner, but if like somebody’s cooking for each other, then, you know, we’ll just kind of treat each other at our own homes. And so I got us like a really nice dinner. I bought a little wine, steaks, baked potatoes, you know, veggies, some dessert.
Reema: Sounds delicious.
Ben: And, you know, and I wasn’t planning on like, and I didn’t, I didn’t Venmo her, ask her for any money because part of it is like, you know, when you care about someone, like I want to make them feel good and to, to share a meal with them.
Reema: It’s a question that comes up in all relationships– at what point do you stop virtually sliding the same $20 across the table to each other and just admit that your finances are intertwined, even without a joint bank account. For Ben, they were already there. But Jay didn’t quite see it that way. On her way to Ben’s place…
Jay: I was getting off the metro, and there’s a Walgreens. And I was like, oh, like, maybe he needs something. And so, you know, I text him to ask him if there’s anything that he would like me to pick up. And so when he said seltzer, I was like, cool, bought it, brought it over.
Ben: She bought me this pack of seltzer for $5 and she had Venmo’d me.
Jay: I don’t drink seltzer. So like, if I was also going to drink it, then I would’ve charged him for half of it.
Reema: Wait, wait, wait, wait. You would have charged him for 2.50?
Jay: Yes. [laughter]
Reema: No!
Jay: Reema, Reema!
Reema: Wait, I don’t, I don’t think I reali- Oh, wow. Okay.
Jay: Yeah. But because I wasn’t drinking any of it, then I charged him for five bucks. Um…
Reema: And was it like an even five or did you include cents
Jay: Did I include some of the cents?
Ben: Some of the times you’ll add the tax.
[Laughter]
Reema: Okay. Okay.
Ben: But I don’t think you did this time, but some of the time you will.
[All laughing]
Reema: Everyone is laughing now but when Ben got that venmo request, he was pretty annoyed.
Ben: it didn’t land right because I had just spent like a good amount of money on this nice meal and not charged her a cent and then she had asked me if um, I wanted anything so I thought I was gonna it was like a treat, and I asked for the seltzer, and then it was followed up with a request.
Reema: Were you surprised that he was upset about it?
Jay: Yeah [laughter] I was surprised. And Ben, please feel free to push back. But like, I feel like there’s sometimes things that I do that, like, don’t sit well with you. And I couldn’t even imagine that it wasn’t going to sit well with you. Like, my mind doesn’t even go there.
Reema: And so how did you bring that up, Ben, when she, uh, when, when you got that Venmo request?
Ben: In past relationships, when things have bothered me, I’ve kind of like stewed on them a little or like talked to friends and then they grow and they get bigger and like, it has never worked out well. So I think the approach that I’ve taken with Jay from the very beginning is just like, I need to find a time to like get this off my chest and talk about it. But it was sometime like within 24 hours where I’m just like, babe I just treated you to this like nice dinner and like you’re sending me money for the seltzer? And then I tried diffuse the situation with a little humor.
Reema: Like…
Ben: Just like, “I’m so glad you got that five bucks,” you know? [all laughing]
Reema: Five dollars and eleven cents!
Jay: Exactly.
Reema: this is four dollars and 26 cents worth of steak.
Jay: It’s very valuable for me to be able to like hear his perspective he like made this lovely dinner and it cost a pretty penny. Um, and it was like, kind of like a gift to me. Um, and I didn’t see it that way. I was like, Oh, like, I’m we’re just like eating dinner together, and like, if he wants me to pick him something up, then like, he should pay for it. Like I’m not drinking the seltzer! But I think just like getting his perspective and understanding the emotion around it. Like he says he doesn’t like to be “nickel-and-dimed.” And so I’ve learned to be better and more thoughtful and mindful about when I am veering into like the whole nickel-and-diming in a way that just doesn’t feel good in a partnership.
Reema: Even in the interview, I could hear that Jay still feels like there’s no reason for her to pay for seltzer that she’s not drinking. But she’s earnestly trying to understand Ben’s perspective. Once the new relationship glow starts to fade, there’s often hard but rewarding work ahead: balancing the need to be right about something trivial with the overall health of the relationship.
Reema: What’s the story you’re telling yourself about why she is so on top of her finances? Like, did you know much about her background at that point?
Ben: I knew enough to like just respect where she was at and what she wanted, but I, I feel like over the last year, she’s been able to like, share particular stories, um, way more about like why she is so meticulous.
Reema: Can you share one of those stories, Jay?
Jay: Yeah!
Reema: That gives us a sense of why your relationship with money is how it is today?
Jay: So with my mom, like, there just weren’t, um, A lot of financial resources, like, and, and that showed up in multiple ways, like her going from job to job, and there was also a lot of like moving from, like, home to home.
Reema: Jay’s parents are divorced, she and her siblings grew up mostly with their mom, in the Bronx.
Jay: There were, like, nights where, like, we didn’t quite know what we were gonna eat, um, and there were some holidays where, like, if I didn’t buy presents, like, no one was getting presents.
Reema: But she’d spend the summers with her dad, who owned his own townhouse in Brooklyn and worked for the city. She was like, okay, I want to be at least as stable as my dad, but I want more for myself. Jay started saving early.
Jay: I think the first time that I got a large sum of money was my Sweet 16. So after the party, I went home – like, literally, like, didn’t go to sleep, like, it was late – I just, like, sat down on the floor and went through, like, all of the cards, because you know, it’s, it’s cute that like people wrote like, “oh, happy birthday,” but then they also like put a $20 in there. And so I was like taking out all the money from like all of the cards that the guests got me and I was like, “Okay, so what am I going to do with this?” And then eventually like I got, I opened up a Chase account. And so being very careful with like how I spend my money and also just being proactive about like how I’m earning money is like very built into my DNA.
Reema: Ben is hearing these stories as their relationship progresses.
Ben: As I got to know her more and like, you know, she opened up more, like, it made more sense. Whereas originally I was just like, this is too much, you know?
Reema: It made him think more about the way he spends money. Ben told me that he’s generally pretty frugal, but that he probably orders too much take out…which, same. And he enjoys buying gifts for friends and tries to spend within his means.
Reema: Why do you think you might be more lax?
Ben: I think, in hearing you ask the question, just made me think that like, I never, I’ve just never had to like really worry about that because luckily my dad has been able to build a law practice that has given me a safety net. And that’s something that like, I’m really grateful for. But I think part of the privilege of money is also not having to think about it too much. And I think there’s pros and cons of that, right? Like, because It is sometimes harder for my family to, like, talk openly about money, like, this was when Jay had, you know, written in about this podcast, it was something that, like, pushed me out of my comfort zone, you know, like, and something that I still feel is pushing me out of my comfort zone because it’s just easier not to talk about money.
Jay: I’m coming from a place of, like, coming up to this middle place, and Ben, it seems like you’re kind of coming, like, I don’t want to use the word down, but like you’re coming to the middle from a more upper place, if that makes sense. And so, even though like at this point like we make generally the same amount of money Like we generally live a similar lifestyle, I think that like our starting places are showing up in where we are right now.
Reema: Like for example, their approaches to Venmo.
Jay: I think when it comes to like Venmo requests not being paid, I almost think it’s like disrespectful. Um, and I think it also, again, comes from just, like, how I grew up. It’s like, you don’t know what position somebody’s in, like, they might really need that money, and if you’re just, like, willfully not paying your portion, I just think that that is, like, inequitable, and also just rude.
Reema: Leaving a large request unpaid – like for say, a hotel room…. I can definitely see why that bothers Jay. It would bother me! But a $5 case of seltzer…I don’t know. There’s something really nice about casually treating someone you love to a little thing that will make their day better, or just save them a trip to the store.
Six months into the relationship, Ben was starting to wonder if Jay would ever be willing to treat him to something without it being a special occasion or gift.
Ben: I was coming back to DC late on a Sunday night and, um, I didn’t, hadn’t had a chance to go grocery shopping, and I didn’t have any food at my house, and I asked her to pick me up a sandwich. And she got me a Potbelly sandwich and did not send a Venmo request.
Jay: Mhmmm
Reema: Aw. Was that, was that difficult to resist?
Jay: No, it was totally fine!
Reema: Jay told us that when she picked up the sandwich, there was a moment where she thought about venmoing him. But then she looked at the bigger picture: he was exhausted from a day of travel, it was a Sunday, and he didn’t have food in the fridge for lunch the next day. She wasn’t thinking about her spreadsheet. She was thinking, “I love Ben, and I want to make sure he has something to eat tomorrow.”
Reema: What’s something you learned from the other person about money and how to spend it?
Ben: I think from Jay, I ask myself the question more, like, do I need this? And like, not, do I want this or can I afford this? I think that, um, it really just helps me kinda, you know, think more intentionally about what’s essential and what will bring me joy versus what might be something that’s extra.
Reema: Ben spends a little less on UberEats, does a little more meal prep at home. And he’s saving more for retirement
Jay: One learned from Ben is to not just think about, like, me in my own little financial bubble. And like how, like, I like to handle money, but also thinking about other people’s bubbles, and just being more mindful and considerate of, like, how they handle money and, um, figuring out a way that, like, we can meet in the middle.
Reema: Also, they’ve been on plenty of trips since that Panama one, and Jay’s since discovered that settling up after the trip is actually kinda nice.
Jay: It helps me to be more in the moment with the activity instead of in the moment with my money. So that’s been wonderful. So, you know, I thank you for that, um, Ben.
Reema: We’ve got a wrap, but final question: Does Ben have any outstanding Venmo’s right now?
[both laugh]
Ben: She sent two yesterday, and I completed them both.
Jay: No, I sent them today! I sent them today.
Ben: And I already completed them?
Jay: You already completed them, like, it was within the hour, yeah.
[All laughing]
Ben: Okay! I didn’t, I didn’t, I didn’t even think that we’d be doing this interview, you know, it just, it just become habit.
[laughter]
Reema: Oh, and one other thing, I was doing a follow up interview with Ben when I asked him a pretty routine question:
Reema: Is there anything else that you just want to clarify or anything that you want to add or…?
Ben: I don’t know if you know, um, but I did propose to her recently.
Reema: Oh my gosh, congrats!
Reema: Obviously I had to call up Jay and get her side of it. She said he planned it to a tee, taking her out to dinner at a restaurant overlooking Roosevelt Island. And then, as the sun was setting, he started telling her how much he loves her…
Jay: I was like, oh my gosh, like it’s happening. So like, you know, I was listening to like 75 percent of what he was saying.
Reema: Right, of course, ‘cause you’re also trying to process. You’re like, what is going on? Yeah.
Jay: Exactly! I was like, Oh my gosh! Oh my gosh! Um, yeah. And then he like got on his knee and proposed yeah, it was, it was just so very sweet.
Reema: Their wedding is set for next year. And of course, it’s all being planned in Jay’s very elaborate spreadsheet.
We’re so curious what your take on this is – are you more of a Jay or a Ben when it comes to money? You can call and leave us a voicemail at 347-RING-TIU, that’s 347-746-4848.
Or if you have a money fight you want to share, send it our way at uncomfortable@marketplace.org. And to be clear, it doesn’t have to be with a romantic partner! We want to hear your roommate fights, sibling arguments, friendship tension, or your neighborhood drama. Also as always be sure to check out our newsletter. We’re gonna include some fun romcom recs this week. If you’re not already signed up for that you can do that by clicking on that link in the show notes.
Alice Wilder: This episode was produced by, me Alice Wilder. I wrote the script, and Marika Proctor provided production support. Zoë Saunders is the show’s senior producer. Jasmine Romero is our editor. Sound design and audio engineering by Drew Jostad. Bridget Bodnar is Marketplace’s Director of Podcasts. And Caitlin Esch is Supervising Senior Producer. Francesca Levy is the Executive Director of Digital. Neal Scarbrough is Vice President and general manager of Marketplace. And the theme music is by Wonderly.
Reema: Alright I’ll catch y’all next week.
Ben: She was creating her budget and she’s like, okay, you know, I’m going to just give 50, $50 this month for eating out. And I’m just like, so you, you want me to take you to like fast food twice or like what?
[laughter]
Reema: I know, 50? I’m like thinking about how I spent 50 in the last three days on food.
[laughter]
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