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The Awkward, Uncomfortable Art of Getting Someone to Pay You Back

There are no hard-and-fast rules for navigating the agony of asking someone to return the money you loaned them, but there are definitely a few good guidelines

When I went on my first ever date, I anticipated that the boy would pay, largely because my mother had drilled it into my head that the boy always had to pay. At 13, I hadn’t picked up on the subtle sexual exchange that this old-fashioned arrangement implied — that the boy would pay and I, in turn, would do something he wanted, something erotically commensurate with the amount of money he’d just spent. All I knew was that The Boy Would Pay, so I didn’t bother bringing money to the movie theater. 

My date had absorbed no such information about who needed to pay for whom, and initially split off from me in the ticket line to purchase a single ticket for himself. I panicked and adhered myself to his side so that he had no choice but to acknowledge me at the point-of-sale, at which point I admitted I hadn’t brought any money. He looked peeved, but said those seven little words that are forever plaguing human relationships: “That’s okay. You can pay me back.”

That was the first time I ever found myself in unwitting debt to someone I cared to impress, but it wouldn’t be the last. Long gone are the days when The Boy Paid every single time, which — make no mistake — is a good thing. To my mind, if a boy wants to pay for sex, he should do so straightforwardly. I don’t need any more men ponying up for dinner when what they intend to pony up for is pussy, wage gap be damned. Life is complicated enough without parsing out all those extra rules. But one significant downside to the loss of this reliable arrangement is that we now have exponentially more situations in which we have to pay each other back, an age-old tactical headache.

Before mobile payment-sharing services like Venmo came along, it was all I could do to keep a grip on my sanity. “I ordered a salad and water, and you ordered a sandwich with a beer, and I’m paying cash, and you only have a credit card, and I only have 50s” — literally just shoot me, I can’t do this sentence anymore. Venmo simplified things inasmuch as we no longer needed to do such elaborate exchanges in the moment. We could take our time calculating the exact quantities we owed and pay them later. But even Venmo can’t take the sting out of perceived lapses in debt etiquette. It makes it easier to pay debts, not to negotiate them.

The problem is that my friends and I don’t have enough money between us to maintain one of those long, mature chains of having one person cover the entire dinner this month while the next person covers it the next month. So we end up nickel-and-diming each other to a ridiculous degree, Venmoing the same $10-for-burritos back and forth until, presumably, we all die and our Venmo balances are finally lost. Or, as my pseudonymous friend Helena puts it, “Nobody wants to care whether I remember to send them their little $10 for lunch, but we’re all equally broke, so we all end up caring so much.”

That explains some of the phenomenon, at least from our side: We’re too straightforwardly poor to just suck it up and eat someone else’s minuscule debt. We need to be paid back for coffee or drinks because we aren’t capable of floating even small sums. But what about the people who can afford to take the hit and just refuse to? I consulted with a lawyer I went on a couple dates with back in 2011, and after getting over the initial horror at hearing from me in the context of being asked to give a quote about why he’s such a cheapskate, he agreed to do so under the pseudonym of my choosing.

So, Dick, why did you spend almost a year texting and calling me about the $19 that I owed you for a pasta from fucking Vapiano? “Because it’s fair,” he points out, not incorrectly but very pedantically. “It would be a different story if we’d agreed that I’d cover you ahead of time. You just assumed I’d pay for you without even asking me to do it.”

I have to admit that Dick has a point, albeit a super annoying one. Yes, in a perfect world, matters of petty financial intercourse should be made clear and obvious. In a perfect world, I could have told this man I had been on one date with that I was in dire financial straits due to being a college sophomore cobbling together a sub-poverty-line wage from my two jobs, and he could have explicitly offered to buy me pasta with his attorney’s salary, and we both would have been all the more relaxed for how simple and explicit we’d just made the world for ourselves. 

The unfortunate crux of the problem is that the old gender roles are no longer so predictable as to take that stress off a heterosexual date, but we still live in a world that’s governed by people’s financial needs, which it turns out are still rude to even discuss. Dick had me in a catch-22, and he knew it. (He claims he didn’t know it.) If I’d explicitly asked him to pay for me, I was in danger of being graceless and rude — to say nothing of what I’d be implying sexually, which I really didn’t want to imply. If I’d explicitly refused to pay him back, I would’ve seemed churlish and stingy. And if I’d sucked it up and had sex with him for the price of a Vapiano pasta, I would have been so annoyed with myself. 

There’s nothing wrong with selling sex, or with doing so for an inexpensive rate, but the fact remained that I didn’t want to do it and felt that I was being boxed into it. The only option left to me was to play phone tag for a year over a debt that amounted to approximately three hours of tips in the coffee shop where I worked. It was a suck-ass option, but weren’t they all?

I can advise no hard-and-fast rules for navigating the agony of asking someone to pay you back, but I can suggest some guidelines. One, use common sense about the money that you and your friends have to spend in the first place. If one friend makes a substantially higher salary than the rest, that friend can either cover everyone else at the nice place of their choosing, or agree to do something cheap. The Venmo collection at the end of the night feels much lower stakes when the bill’s total is low. This also means that Dick’s argument doesn’t really hold water — if one party is a corporate lawyer and the other makes a single-digit number of dollars per hour, the layout of monies owed becomes obvious on its own, without needing to be made explicit the way the lawyers and bean-counters of the world want it to be.

But also, I admit that I grudgingly respect Dick’s balls in this matter. He felt he was owed a debt and he came at me with the intensity of 10 collection agencies. I will always hate him for this, because no matter what mental gymnastics he still performs to convince himself otherwise, he had the money and I didn’t and he had no right to harass me like that. Yet in situations where one person’s debt puts one of their friends under legitimate financial strain, it should be acceptable to say so explicitly — Dick was right about that. It shouldn’t be embarrassing to admit that you simply can’t cover your buddy’s pho this time. Most of us can’t cover the proverbial pho every single time! There are no temporarily embarrassed millionaires here!

I’ll leave you all with Helena’s final thoughts. “They have to pay you back,” she advises. “If they can’t pay you back, you can’t cover them again. If they actually can pay you back, they’ll do it when you tell them that part, and if they can’t, then so what, you spent twice as much lunch money to find out that your friend is in bad financial shape and needed your help. But never spend money you really truly can’t afford to lose on finding that out.”