The first charge was serious. I had invested $12 in a 36-pack of condoms from Amazon because I thought our relationship was finally at the point where spending $6 on a three-pack at a bodega was silly. It might not have been a future investment like a couple's vacation or engagement ring, but I had decided to invest in whatever my romance had turned into. Not two weeks later, my investment tanked. Less than three days after drunkenly telling me he loved me, the guy I was dating unexpectedly dumped me. But instead of turning to Tinder to move on, I turned to another app: Venmo.

We had only Venmoed once or twice in our short relationship, but I knew it was an app he used frequently with his friends. Like most people our age, public charges had become their own form of emoji-branded social media. In hindsight, the immature charge labels between him and his friends like "douche meat" and "Bon Iver merch" should have been red flags.

A few hours after our last text fight post-breakup, it was clear he was no longer interested in continuing the conversation. With nothing left to inventory than our wasted time together but a lot left to say, I started to get more and more annoyed. I had immediately blocked him on Facebook after the breakup, but my morbid curiosity got the best of me. I pulled up Venmo to see what pink-haired freelance graphic designers of my imagination he was Venmoing with. That's when my inspiration struck. I charged him for the condoms.

And I waited. Nothing. Maybe he had blocked me on Venmo. He never listened when we dated anyway, so what did it matter if he even saw the charges? I angrily typed away on my tear-smudged iPhone keyboard. "All the time I spent with your friends who hate me." $18.62. "Drinks with my friends who were nice to you." $22.

I had used the app before as a means of communication — sending small amounts to friends who were mad at me to remind them I exist, a cutesy ".02 my two cents" here and there. But this was different. While I did sincerely want money back for the condoms, my newfound means of catharsis was too addictive to quit. With each charge, I felt like the resentment that had built up in our uneven relationship was finally being heard.

Pecuniary regrets color all relationships, but it's rare that we ask people to pay us for our time and emotional expenditure. We approach modern dating like a contract, trading our time and the associated costs for the prospect of love. Of course, with one big, fat caveat — if the other party doesn't deliver, we get nothing back. But it hasn't always been that way.

"There were definitely cases in the 1910s and 1920s where fathers sued young men who had slept with their daughters, while being engaged to them, for 'seduction under promise of marriage,' Moria Weigel, author of Labor of Love told me. "These men were ordered by a court to offer financial compensation after the end of a serious dating relationship."

Of course, those laws reflected a time when a woman's entire economic prospects rested on her marital prospects. In our era of hookups and aversion to "defining the relationship," it would be hard to argue that your latest Tinder match ruined your life by taking precious weeks off your social calendar. Unfortunately for the modern woman, the "heart balm laws" that let jilted girlfriends of yore get revenge no longer exist in most states.

Was I a shitty person for asking my ex to pay for time I had given him freely?

From a historical perspective, my actions had some precedent. Sure, I wasn't asking to be paid back after just one date like the man in this viral story from last year, but was I a shitty person for asking my ex to pay for time I had given him freely?

I took an informal survey, and according to friends, yes and no. Some of them had even acted similarly, reporting asking for a coveted item back. One friend had to demand for her Gameboy back not once but twice. This was all too familiar — I once spent six months trying to get back a book and a rare record that I had given an ex before our breakup. He sent me $50 but I fought tooth and nail for them both (the book was very special to me but the record was just pettiness). In that case, I couldn't have cared less about the monetary values of the objects — I had given him something sentimental and I wanted to undo it. Most friends I talked to cited the sentimental nature of reclaimed objects as their biggest reason for requesting them.

According to Weigel, asking for gifts back is a legacy of our dating culture that has endured since the beginning of going steady. "Interestingly, during the 1940s–50s there was the custom of exchanging gifts with 'steadies' that you would give back when you broke up," she said. (Gifts like rings or varsity jackets, mostly. )"There are historical antecedents for both returning gifts during a relationship and keeping them," Weigel continued.

But not all breakup finance is about sentimentality. And it turns out I wasn't alone in using this instant-gratification money-demanding technology to ease post-breakup pain.

"Before my college boyfriend and I broke up, he gave me his bed, because I still had one more year left at school. I was supposed to pay him $200 for it, but forgot and never did," said Madison, 22. "Seven months after the fact, I get a text from him asking me to Venmo him the $200. Better late than never I guess."

For another friend, it was the reverse — her ex offered to Venmo her for a gift she had just bought him shortly before they split.

It seemed people used Venmo to neatly erase their past relationships, not redeem them.

"I didn't accept the Venmo," said Allie, 20. "I was mostly annoyed because I figured he knew I wouldn't accept it and thought that would make up for the out-of-the-blue breakup."

One guy reported his ex-girlfriend Venmoing him rent money even though she no longer lived with him. It seemed like accounts of guilty exes paying up were endless, but I was pressed to find one case of a flat-out therapy bill or something of that magnitude. It seemed people used Venmo to neatly erase their past relationships, not redeem them.

None of my friends had Venmoed their ex for their time as I had; as my one friend said, she "didn't have the ovaries too." The emotional labor of modern dating isn't just something we agree to; we're used to it being an exploitative economy.

According to attorney Gavin I. Handwerker, in New York, the only gift an ex would be legally obligated to return or pay for is an engagement ring. "If the 'gift' was a wedding ring, it is under NY law what is considered a gift in contemplation of marriage."

As for emotional damages?

"There is no shot," Handwerker said. "Claims for emotional distress are really frowned upon, especially in these sort of circumstances. I could see a situation maybe if the person were duped into giving the ex something but even that would be a hard-pressed case."

Ultimately, my ex did Venmo me my requested $52.62. However, as with most technology, the thrill was fleeting. As soon as he paid me, I realized it really didn't fix anything in our relationship. Venmo had neither redeemed or erased the time and feelings I had given.

But at least I could afford a pizza and bottle of tequila.

Follow Tonya on Twitter.

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