Who Picks Up the Check in the Tinder-verse?

Three millennials talk about the future of money, dating, and what’s changed since ‘Sex and the City.’

Illustrations by Yasmine Gateau

It’s time to update America and Earth on the state of how people deal with money issues within relationships — marriages, friendships, Tinder dates, and everyone in between. I myself am surprised how far we can come in a couple of short decades — I rewatched Sex and the City and learned it wasn’t that long ago we were still puzzling over what it “means” when a man resents your professional success!

To discuss these issues, I’ve roped in two people who have used money before in the presence of other humans: Jaya Saxena, who is married, and Cale Weissman, who is filing-status single but currently in a relationship.

So Jaya and Cale, consider this scenario: two people have swiped right on each other on Tinder. Emotions are running high, the vibes are there. They go on a date. Who pays??

CW: I don’t think I’ve ever been on a first date where one person paid the entire tab? Mind you, I’m a notoriously anxious person in these situations, so I wouldn’t be surprised if someone offered to pay the full tab and I had minor freakout. Of course, the majority of my dates have been with other men, and I bet that changes the dynamic/expectations a great deal (which is sad because it’s 2016, people!).

JS: Yeah, I think you just sort of…figure it out? You talk to each other and figure it out! Like how your parents take you out to dinner and you’re like “can I pay?” and sometimes they’ll let you split it and sometimes they just won’t let you pay. Like that, but with someone you’re romantically interested in.

CW: Yeah, I don’t know if this is the same for you, but I now remember going on dates with people who were very adamant to pay the entire check and it was kind of a turn off.

CJ: This is so interesting to me! I thought I had this all figured out but you guys are making me doubt myself. My system used to be, the initiator, AND/OR chooser of the venue, pays. Like, to exaggerate this for the sake of making a point, if you ask me on a date and I say sure and you say “great, let’s go to Eleven Madison Park!” You’ve made it awkward for me to say “well, I’m not the most fantastically wealthy person.”

JS: Uhh, I absolutely would be like “just so we’re clear you’re paying for Eleven Madison Park” if that were mentioned because I would not want to get there and realize I’m on the hook for $600. In most situations, dates or not, I tend to assume I’m paying my own way until proven otherwise.

CJ: The “who pays” rules have long revolved around gender in a retro way. How do they apply in our modern times where (gasp) men date men, women date women, genderfluid people date bisexual people, etc?

JS: This is why feminism is ruining our country. JK JK JK. But right, those rules existed because it was assumed “the woman” wasn’t making money, so the man had to pay. And now there’s no way to assume who makes more, and it’s not very polite to be like “okay before we go out to dinner can you show me your W-2.” Honestly, I think it’s whoever offers first? The one “rule” I generally hear is whoever initiates the date is on the hook to pay, but I also think it’s just fine if you’ve been asked on a date and offer to pay for your half, or to alternate rounds of drinks or something.

CW: Wow, that rule sounds awesome and now I want to reactivate my OKCupid and ask some people for a refund. JK (?). But really, my experience has been *generally* going dutch (that’s the lingo, right?) or buying rounds, and I honestly do think gender had a bit to do with it, meaning that when two men go out on a date there’s no centuries-long cultural norm to subscribe to.

CJ: I’m so glad we have all risen together to fix the problematic who-pays scenario. You guys have given me a lot of confidence that maybe everything will someday be OK and no one owes each other sex in exchange for a couple drinks and maybe a burger. Second corollary: do these rules vary for other dating platforms, e.g. Bumble, where women are responsible for initiating contact?

CW: I’ve found that different dating apps make for different expectations, but that doesn’t necessarily translate to the economics. Like, my Tinder dates were mostly very casual… more like a friendly convo that could lead to something else? And I’ve had other more “formal” dates using more “serious” apps and websites. But in either situation the bill would usually be split or purchased in rounds. (I also knew someone wasn’t for me if I bought the first round of drinks and they didn’t buy a second.)

JS: I think it depends on the type of date more than anything, that “formal” date versus whatever else. If you’re doing dinner or some committed, lengthy activity for a first date, then it feels like it’s on at least somebody to pay. But if you’re meeting up for a drink or coffee it’s a lot more flexible, because it’s both easier to look generous and say “I got this” on two coffees, or just order your own drink.

CJ: I once went on a coffee date (OkCupid) and the guy made a big show of paying for my $2.50 tea. Later in the date he spontaneously started using a French accent. We did not go out again! But say that we did, for the sake of another scenario — how would the pay rules have settled out over time with me and Pepé Le Pew? Seems like it used to be that people would tend to split things the longer they’ve been together, depending on their relative incomes. Still true?

JS: My husband and I have a joint checking account, so it’s sort of ridiculous to pretend that one is taking the other out when most of it goes into the same pot. Back when he was making a lot more than me, he paid slightly more in rent, but when it came to dinner or dates we did things that I could afford as easily as he could. It always icked me out when I heard of couples living together but one made twice as much so they’d be living the high life while the other was pinching pennies. If you’re in a relationship like that you should probably be splitting things a decent amount? I don’t know.

CW: I don’t share an account with my boyfriend, but we’ve sort of created a nebulous system of equivalents. For instance, I paid for dinner the other night so he bought me three drinks last night. Before, it was more rigid (probably because of my anxiety) where I would Venmo exact amounts or we would split bills. We still sometimes do this (and now that I think of it, it’s kind of random when we do) but more often than not we have an imaginary list of who owes what.

CJ: I feel like Venmo enters into my relationship mostly when either the amounts of money changing hands are large, $20+, or one person feels like they’ve been footing the bill too much and they get testy about buying someone else like, a $3 donut. Venmo saves the day, or maybe just serves to highlight communication issues. Maybe both! So let’s say you have roommates, or one very special roommate who you are perhaps in a legal union with of some kind, you lucky person ;). How do you split the expenses of living together, both from a functional perspective (i.e. who pays how much) and a practical perspective (how do you manage your funds/exchange/repay each other money)?

CW: This question is giving me PTSD. In my first Brooklyn apartment I lived with three other people, all friends. And we had this very weird system where we would share everything — including groceries — and record the amounts. The ferkakta expectation, however, was not to pay everyone back in a timely fashion but to get the next round. It was an honor system in writing. It sounds good in theory but it was terrible. It ended up with someone owing another person hundreds of dollars because they paid internet every month but never got groceries… And others saying “NBD” while thinking “OH GOD THIS IS A BIG FUCKING DEAL.” It was just bad. Now I live in a three bedroom and we also use a digital ledger (the website Splitwise, which I HIGHLY recommend!). On it, we record real bills — electricity, gas, internet. And then every few months or so we try to settle up (generally via Venmo). As for smaller things that we share (ketchup, toilet paper, cooking oil), it’s usually pretty casual — an issue of who’s available to buy it when we’ve run out.

CJ: Cale, this is my nightmare. Honor systems like this give me deep anxiety because I know I will never have the balls to play them to my advantage but will also never have the balls to stand up to someone who is playing them to their advantage and will always end up paying a lot of money for nothing. Thus why I live alone! My cat doesn’t pay for anything.

JS: Ooh I can answer this! Okay, my husband and I have a joint checking and savings account, and our paychecks go fully into there, and we pay all our living expenses — rent, utilities, groceries, travel together — out of there. I have a personal account and a personal credit card that I’ll use sometimes if I want to buy him a gift and don’t want him to see, or a dress or a haircut or something, but that’s not a hard and fast rule. Any larger, personal purchases (like, “I’d like to buy this $800 suit”) we run by each other anyway. But with roommates it’s way harder, especially with groceries, because it makes no sense to get like, three bottles of mustard so everyone gets their own. For a while I lived with my BF and a roommate, and I think we just had a running tally on the fridge every month of how much we spent, but I have no idea if that was a better system than any other.

CJ: And you make roughly the same amount of money so you’re throwing in roughly the same amount every month?

JS: Exactly. And the assumption is that this all evens out over the course of a lifetime. For a while he was making a lot more than me, so he was contributing more to the pot. And then he had an injury so I was doing the heavy lifting for a while. But even if we weren’t making the same amount, I think we’d keep the same system. My view is that the money I make is to facilitate my life, and my life largely involves him, so I want him to have use of it as much as me. Though it helps that I trust him not to blow it all on something stupid.

CJ: This is maybe a weird question but, how much do you consider someone’s financial habits when deciding to date them? Jaya this doesn’t apply so much to you, but how do you think one should fit that into the dating process?

JS: I’m not sure if I ever really considered it, though obviously it’s something to be considered! I think it’s just part of overall compatibility, which you try to figure out at the beginning of the relationship.

CW: Hmm, that’s a good question. It’s definitely never been a conscious consideration. I have been in many different financial situations myself and have never been the most financially prudent individual, so I try not to judge someone based on their tax bracket or how they deal with money. I suppose I’ve met some stingy people, or people with a very foreign financial ethos, and I’ve taken note. But these observations have never been deal breakers, per se.

CJ: Do you think people are spending more money on dating overall with the new availability of dating opportunities, thanks to apps and stuff?

CW: In New York, probably not. Perhaps it’s true about other places, though. As far as I know, casual dating in cities has always been a thing… I mean, just look at Sex and the City, right? I don’t think the apps have created an uptick, but perhaps just changed how people meet each other. Bartenders I know often talk about how obvious it is when people are meeting for the first time on Tinder. And the corollary is that they see fewer people meet “organically.” That being said, I grew up in small-town Western Massachusetts, and I’ve heard that people are now using Tinder and other apps there, and it’s like a new world of dating has emerged. So perhaps in non-urban areas people are spending more money thanks to the new technology.

JS: I keep thinking of talking to my grandma about dating, and how she always said that when she was growing up and in college, it was totally normal and expected to be dating multiple people at once. You had your Friday guy and your Saturday guy and going on casual dates was just no big deal. So it’s funny to me whenever I see people fretting over how online dating makes more dates happen because it was only a short amount of time ago that that stopped being the norm! I’m not sure if it makes people spend more money though. If you’re taking someone out to dinner three times a week then yeah, but if you were Seamlessing those nights anyway it’s not much more than you’d usually spend. Plus if you’re worried about money your “date” can always be a nice walk in the park or something.

CJ: How do you think dating is going to change more, if much or at all, in the future, long or immediate term? Creepy genetic matching? Using all of the data collected by marketers via Facebook over an entire lifetime to match you with potential dates?

JS: Oh god this is terrifying, though I do think there’s already a genetic service in Iceland, but that’s just because the likelihood of you accidentally dating your cousin in Iceland is really high. If anything, I think it’d become subtler. The main thing that seems to still frustrate people about online dating is the obviousness of saying what you’re looking for, so if there were some technological way to make dating seem spontaneous and serendipitous again, that would be pretty popular.

CW: Yeah, I’m with Jaya on this one. I think people balk at overt technological overreach when it comes to personal lives. But companies like Facebook and Amazon are masters of insidiously collecting all of our data to quietly make decisions for us. So I wouldn’t be surprised if in the future the intent is to more subtly match people. I mean, who wouldn’t love to think they met their significant other in a completely random way? Even though online dating is everywhere, people still feel a slight stigma admitting it was a website and algorithm that matched them. So the dating future may be creating quieter ways to do just that.

CJ: This is sort of a personal question but: how do you do gift-giving these days with friends, family, significant others? I will admit I buy more Amazon gift cards than is healthy, but I also have those siblings who refuse to tell me anything they want EXCEPT an Amazon gift card. They are no fun and it sucks.

JS: It’s easy because I’m terrible at giving gifts so I just generally don’t do it. I just don’t expect birthday gifts because I’m almost 30 and, in my opinion, too old for that shit, so it doesn’t occur to me that other people expect them. I’m probably a bad person for that. For birthdays a lot of my friends will plan a dinner and we’ll all chip in to buy them dinner and their drinks for the night, and that’s just fine with me. I’ll get my parents Christmas gifts and my husband a birthday present, and that’s about as much as I can handle. This year we actually had a bunch of friends chip in and get one friend Hamilton tickets for her birthday, which was pretty cool on us I think. I’m just glad when someone else plans it.

CW: Lol, Jaya, I’m the exact same way. I am so bad at giving gifts. But I make up for it by trying to be extra generous during celebrations. Like, when it’s a close friend’s birthday week, I will usually either take them out for a meal or pay for their drinks. This is pretty much what I would want for my birthday, and I think it’s better than agonizing about what to buy someone.

JS: Yes! I love being the one buying drinks at celebrations. And obviously what I want to be doing during someone’s birthday is what’s important.

CJ: What about weddings? I’m going to make this immediately intense: have you ever, would you ever send a wedding gift via Venmo? I have not yet, but was recently faced with mailing a recently-married set of friends a check, and I sincerely thought about just Venmo-ing them.

JS: OMG no. Maybe this is an etiquette hill I will die on but the thought of Venmo-ing a couple a wedding gift is slightly horrifying to me. Even though it’s not like I read any of the cards people gave me wedding checks in, and money is money. But I wouldn’t want everyone else on Venmo seeing how much I was sending someone! I sorta hate that about Venmo. I’ve given checks for weddings, but I try to find something on a registry (if they have one) that looks impressive but it comparatively cheap. Like some $35 platter that’ll make me look really generous even though if I gave a check I’d feel compelled to give $50.

CJ: Oh god I totally forgot about the public-feed thing on Venmo. Bullet dodged. What if it were a private transaction? I think you can make them not show up to your friends. Or what if it were like Square Cash? Please enable my rudeness.

JS: I think I’ve made it so that it’s private? I have no idea. It still makes me put in a little emoji and I hate it. I think it’d really, really have to depend on the couple though. I’m sure there are couples who’d think it was just fine, or even totally convenient and fun, but you’d have to really make sure of that otherwise you’re going to come off as a jerk.

CW: Yeah I can’t imagine Venmo-ing someone on their wedding. Maybe I’m old fashioned but I think on occasions like those it’s the actual tangible object that means something, which is why checks still seem best when giving money. Recently I’ve noticed people asking for donations to fund their honeymoon? The digital age, man. But I’m in the same boat where I try to find something relatively affordable on the registry. The first wedding I went to as an adult, I freaked out because I forgot to bring a gift. So I went to a nearby new age-y gift shop and bought some weird kitchen item that was made of crystal (I think). The gift really didn’t fit the bride or groom but I didn’t know what to do. Then, a week later, I told this story to a friend and they informed me that I had six months to buy a wedding gift!?

CJ: Ok, I’ve always wanted to ask someone this: have you ever gotten a gift from someone and been like “Oh! So nice!” And then gone on the internet and looked up how much it cost them? I have, and would freely agree with anyone who called me terrible for doing that. Never possible in the old days, 100% always possible now.

CW: Oh yes! I think this is in the boat as Googling someone before you go on a date with them, right? This is also why things like nice-looking used books and vintage-y antique-y tchotchkes are the best gifts.

CJ: That is so crafty, I’m stealing that strat. Now that I think about it, my boyfriend pulled this on our first gift giving occasion; he and you are much smarter than me.

JS: I haven’t, but I’m definitely going to now.

Cale Weissman is a Brooklyn-based freelance reporter.

Jaya Saxena is a freelance writer who lives in Queens with her husband, who is also a freelancer, and two cats who don’t do shit.

This discussion has been condensed and edited for clarity.


Sponsored by SoFi, The Future of Money is a series of stories that explores a world in which banks no longer control our finances. Learn more at SoFi.com.