When I was 21 and very, very dumb, I met a guy on a trip to Europe whom I quickly became obsessed with. Despite having only kissed him once, and having spent a grand total of three afternoons with him while in his country, I drained nearly all of my non-existent checking account to host him in America for a full two weeks (much to the dismay of my four roommates at the time). Looking back, I’m lucky that he turned out to be just incredibly lame, instead of an axe murderer. But the heart wants what it wants, and my heart at that time wanted to spend close to my last $1,500 showing this guy around my part of the U.S. for the first time, despite barely knowing him. To make myself feel better about my incredible waste of money, I spoke to 13 people about the craziest thing they’ve ever done, financially, in the name of love. It turns out, my experience was much closer to normal than I’d thought. People are crazy when they’re seriously crushing.
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“My ex was a grad student who made basically no money, and was drowning in debt, so for the year that I was dating him I essentially subsidized his whole life. This would not have been so bad (I was making good money at the time, and was deeply in love with him), but I found out that he was cheating on me for the last three months with a girl from his program. When I forced him to tell me how he could do this behind my back for so long, he told me that ‘it made him feel like more of a man to be with someone who didn’t take care of him.’ Yeah.” –Katie, 29
“I bought [my lame ex] a pair of Jordans, which was a bad move because 1) boys don't deserve good shoes, 2) I should have bought them in my size and kept them, and 3) I created a monster because now he is a fucking sneakerhead.” –Rachel, 26
“I think the top one was the full set of Sex and the City DVDs, but the range goes from Valentine’s Day flowers to everyday flowers to a (small) TV to, ahem, private bedroom items. Recent rule of thumb: never spend money on flowers until you're in an actual relationship with someone. But I’ve even done the whole "donate a goat to a family in need" for someone who didn't like to receive gifts. You know, those programs where you spend X amount of money and the organization gives a family in a developing country a farm animal and it can be on behalf of someone. I did that.” –Anthony, 30
“I was dating this guy who was very redneck—which I was depressingly attracted to at the time—so I wanted to impress him by getting stuff that was ‘in his taste.’ I got him a full set of camo covers for his truck seats, camo underwear, and a camo jacket. Despite being incredibly ugly, that shit is really expensive. And I’ll never get that money back.” –Hope, 26
“At my best friend's wedding, I got really sick and had to leave early. I was sharing a room with some of the bridesmaids in one of those business hotels in nowheresville Jersey. When I texted my boyfriend to tell him I was sick and had to leave, he decided to come up and spend the night. I was only a half hour from home but too sick to travel myself. So we ended up buying another room in this crappy hotel, and then the next day, when it was time to check out, we decided to stay again because we liked being in a hotel. We spent an entire rainy Saturday in the hotel, ordering delivery from the liquor store and room service, obviously. It wasn't an extravagant amount of money but also totally needless, and he turned out to be totally thankless. Also, he arrived at like 4 a.m. so we paid for a full night in a new hotel room for something like seven hours.” –Carole, 28
“In terms of quantity, it’s definitely express shipping on flowers. But the most painful item was probably a Dooney and Bourke bag. It had a design that looked like kids drew hearts on it with crayons and was the most hideous thing I've ever made the physical effort of swiping a debit card for.” –Chris, 27
“When I was 22, I met this girl online in a forum I frequented about a video game—yes, I was kind of a geek—and I fell head over heels for her right away. She was three years younger than me and still lived with her parents, so when it came time to do the big online relationship meet-in-person thing, I offered to help buy her ticket. I did, and she came to stay with me for a week (on the couch of course, because I didn’t want her to feel pressure like that). I didn’t get catfished or anything, and she was everything she said she was in person, but I found out almost immediately that there was someone she actually wanted to come to my city to see, and it wasn’t me. She essentially friendzoned me the second she got off the plane and left me on day two to spend the rest of the trip with the guy she really had feelings for. I was essentially her desperate nerd sugar daddy, minus the sex.” –Max, 25
“I bought a Prada dress for a black-tie event for my boyfriend who was up for a design award. He didn’t win, I spilled wine on a $1,000 dollar dress, and now he’s married to a woman he met at that job. Go me!” –Caroline, 33
“The dumbest I've ever spent money on for love is the $600 I paid to get out of my lease early so I could move somewhere with the person I love. In my defense, I was also leaving for a new job, but I don't think I would've been nearly as hasty with the timeline and so okay with eating that $600 if it weren't for the guy. When I move again (whether for myself or with someone else), I need to plan 300% better.” –Maya, 23
“I have a really bad habit of spending money on lingerie that I think is going to be sexy and really jazz up whatever relationship I’m in, but each time I barely end up wearing it and then it ends up living in the back of my drawer, to be totally forgotten about. And once, I was dating this really hot, really successful older guy that I wanted to impress, so I went to La Perla and spent several hundred dollars on a bra and panty set the night before a big dinner date. He took me out, we drank cocktails and a bottle of wine over dinner, then went out to a jazz club afterwards and drank until 3 AM. By the time we got back to his apartment we were both wasted, he had whiskey dick, and we passed out in our clothes without me even revealing the super-sexy underthings. We broke up a few weeks later, and the La Perla never saw the light of night.” –Melanie, 30
“I met a guy traveling in Europe and got really swept up in the experience. When he went home to Australia he offered to split a plane ticket for me to visit him, so I did, despite have barely any money left in my account and no job prospects lined up either in the U.S. or abroad. It didn’t work out.” –Nat, 27
“I took my girlfriend to King’s Dominion and she wanted this, like, six-foot-tall stuffed bear. I couldn’t win, but I spent literally 20 rounds of the game trying to get this dumb fucking thing. I ended up asking the guy how much it would cost and bought it, and between the game and buying it, I spent nearly 300 bucks on a giant stuffed animal for this chick I had not even been with the whole summer. And she dumped me by Thanksgiving. I hope that dumb thing caught fire.” –Nick, 26
“I was dating a girl for three months when her lease was up in NYC and she didn’t have enough money for a deposit on a new place, and was scared of finding a roommate on Craigslist. Stupidly, I offered to let her come stay with me while she continued the search and saved up money. The relationship went sour within a few weeks of living together (she was a huge slob), and I ended up with this chick just awkwardly squatting on my couch and eating my roommate’s vegan food for the next month until we had to sit her down and ask her to leave. And she ended up getting a Craigslist roommate in the end, anyway.” –Steve, 30
Chelsea Fagan is the founder of The Financial Diet, a (non-boring) blog about personal finance. She is on Twitter.
