Your Bad Date Stories

Reader-submitted tales of love gone horribly awry.

By: Tanya Pai

There’s a reason Valentine’s Day is also known as Singles Awareness Day: When you don’t have a date, it can start to feel like you’re the only painfully alone person on the planet. But dating isn’t always what it’s cracked up to be. We asked for your stories of dates gone bad—and boy, did you deliver. From projectile vomiting to accidentally speed dating with senior citizens, these tales of romantic woe will remind you sometimes being single ain’t half bad.

Friends With . . . Benefits?

I was out with a guy about five years ago who was my friend at the time, but we were sort of verging on becoming more. We went to a house party in my neighborhood and he got ridiculously drunk. Even though he was a sloppy mess, I still needed him to walk me home when the party died down around 2 or 3 AM. (We were in a not-so-great part of DC and I didn’t feel safe walking alone, though in his state, I’m not sure how much protection he really could’ve offered.)

We got to my building, and he asked if he could just crash at my place, since it was so late and he wasn’t really in good shape to walk home or find a cab. Given that he was a friend and that I was sort of worried he might turn up in a gutter somewhere if I sent him packing, I agreed, but told him he had to sleep on the couch. Fast-forward a few hours to about 6:30 AM. That’s when I awoke to the sounds of him getting violently ill in my bathroom. I pretended to be asleep—as I tried not to dry heave—and luckily, he saw himself out when he was done.

That afternoon, I was leaving to run some errands when I saw that someone had also gotten sick all over the front steps of my apartment building. I later confirmed that it had, in fact, been him. So not only had he left quite an impression on me, he surely left one on all my lucky neighbors, as well.

Going for Broke

I went on a date years ago with who I thought was a fairly nice guy. When he arrived in my driveway to pick me up, he showed up in an old beat-up Volvo. He ushered me over to the driver’s side door and made me hop in through his side because the passenger side door was broken. He then took me to a quaint mom-and-pop Italian restaurant. After dinner, when the check came, he said he didn’t have enough money to pay for it. At that point, I refused to pay for anything because I didn’t bring cash with me. He asked me if I could call a friend or my parents and have them bring me money to pay. When I refused, he walked outside to his broken down car and saw him scrounging around for old change behind the seats (that were littered with trash might I add). He came up with about $10 in loose change and the restaurant took down his name/phone number, so he made arrangements to pay them back at a later date. He then took me back to my house, where I crawled out of the driver’s side door, and he demanded to come inside. I told him I was tired and it wasn’t a good time, and thanked him for the date, but he insisted on using my bathroom. I let him in, he used the restroom, then came out and sat down on my couch. I told him again he really needed to leave. He then approached me and tried to make out with me. I finally threatened to call the cops if he didn’t leave. He finally left after 15 minutes of arguing.

Phoning It In

I went on a second date with someone who seemed very keen on seeing me again. How do I know? From the countless e-mails saying he couldn’t wait to see me again. However, upon arriving late for said second date, he informed me he was very likely about to get laid off. I couldn’t be upset about him being late and expressed concern, but our names were called and we went to have a seat. After looking over the brunch menu and deciding on what we liked he suddenly received a “call” and excused himself and said he would be right back. About five minutes later I looked down at my phone to see this message: “Sorry, I’m not feeling it and neither are you. I don’t want to waste your time. Good luck on finding what you’re looking for.” He just got up and left, just like that. I was stunned and glued to my seat for what felt like an eternity before I was able to return to my senses, pay for my mimosa, and leave. I can only assume he was raised by wolves. A**hole (that part I’m sure you can’t print). [Ed. note: We’re happy to—sounds like he deserves it.]

If Only This Date Came With a Cheat Code

Several years ago, when I was living in Nashville, I met a seemingly nice guy from Arkansas on After talking and instant messaging for five or six weeks, he lucked up on a job interview in the Nashville area, and we planned to make a weekend of it. Up front he made plans to stay in a hotel, and we agreed to refrain from entertaining at my house or at the hotel—he was a total gentleman about it and the one who brought it up. Ignoring the gaping holes is his story (like why a well-employed man would relocate from Arkansas for a position managing a local Kaplan, and why the interview only lasted 15 minutes), I made plans for the entire weekend, and left work early on Friday to meet him. Well, I spent the first hour waiting in a drugstore parking lot while he went to the liquor store to “stock up” and hook his gaming unit up to the hotel TV. Then we went for a quick lunch (which went well), and I ran back to work for a quick minute. Later we met for dinner at a trendy midtown restaurant, where he expounded on his plans to run for local office on the wave of a worker’s revolution (since we hadn’t had one in the US yet, and most progressive countries had decades ago, he was 100 percent sure it was coming soon) and how, in the meantime, he was biding his time with Internet porn. He went on to explain to me that he downloaded about seven to ten new movies a day, which he thought was typical for a normal man; when I asked if this was the case with his male friends he said he didn’t have any. Oh, and that job interview? He faked it—didn’t want me to think that he was making the trip all the way to Nashville just to meet me. Although I offered to split the cost of the dinner, he insisted on paying, and then said he didn’t realize this weekend was going to be so expensive; his liquor store run alone “cost me $60!!!” I tried to continue to talk to him and make sense of what he was saying, and as he realized that the look of concern on my face was genuine, he ended the date (despite my attempts to salvage the weekend and offer to continue with the upcoming plans dutch) and went back to his hotel to “play some video games, so my whole night isn’t a waste.”

Going the Distance

Two experiences with the same guy: 1) We’d been seeing each other for about a month, and I really liked him. One night he said, “It’s a shame we live so close to each other and it’s so easy to see each other.”

“Really?” I countered. “Shouldn’t that be a good thing?”

Then he proceeded to tell me that the best way to tell how much you like a girl is to figure out how far you would go to see her. If a girl lives far away and you still want to hang out all the time, that’s a good sign. But since I lived so close, he couldn’t tell if he was into me.

2) He told me that Valentine’s Day was the easiest holiday and that any guy who disappointed a girl on Valentine’s Day was an idiot. You just have to show any kind of effort, he told me. Anything at all and girls will appreciate it. We’d been dating for five weeks when Valentine’s Day came. I got nothing.

Cold as Ice

First date or 300th, sometimes you gotta remember when you’re in public. Someone spotted this couple (pay attention to the top portion of the clip) during a recent Washington Capitals game. It appears someone got a quick lesson in civility, even when attending a highly contested hockey match. You paid good money for those seats, so always remember someone is watching you on TV.

Mom Doesn’t Always Know Best

This happened to me last February (though thank God not on Valentine’s Day), when I was living in Minnesota. I’d been single for long enough to slightly alarm my mom (to the point where she was openly questioning my heterosexuality), and so shortly after my birthday she told me about something called “literary speed-dating” at the central library. In retrospect alarm bells should have been ringing, but I thought the concept sounded interesting—you bring your favorite book along to speed-dating and talk about that (and I’ve always been the kind of guy better at chatting up women in bookstores instead of bars). I even checked it out online—it got favorable reviews in Brooklyn. Anyway, so I headed on down to the library after work, where I promptly got mugged by a crazy homeless woman with a face like a catcher’s mitt. She kept shouting “FREAK! FRRREEEAAAAAKKKKK!” at me while waving what looked like a homemade shiv in my direction.

I gallantly ran away and told a cop about it. I was just slightly weirded out by this, but I decided to go to the speed-dating event anyway (I’d already paid for the ticket, after all). So I walked in and . . . I was the youngest person there (23 at the time). And I don’t mean by a little bit—I mean by AT LEAST 30 years. But because I’d already bought a ticket—and because by that point I was just rolling with the sheer absurdity of the evening—I stayed. I went through about five “dates” before my senses came back and I got the hell out of there—the final straw was chatting with a very pleasant lady who looked, sounded, and acted just like my 90-year-old grandmother. Incidentally, I had planned to bring To Kill a Mockingbird to the event, but I forgot to put it in my bag and only had a book I was reviewing for work: a biography of Chairman Mao Tse-tung of the Chinese Communist Party (and I was astounded that some of the old ladies didn’t know who this guy was—I mean, they were THERE when he was around, and he was kind of a big deal back then). The next day, I told my brother about the whole experience—and he told me the City of St. Paul had advertised the thing for 55 and up, which would have been good to know beforehand (though admittedly hearing about it from my mom should’ve been a tipoff).

The Naked Truth

My second date with this guy I met on was one of the defining moments that made me realize online dating wasn’t for me. He invited me over to his house to go swimming at his pool, and then take me out to dinner. I drove out to his house, and, granted, it was gorgeous. He gave me the tour and showed me all the furniture he had built, along with the upgrades he made to his house. We then hopped into the pool, and as we began talking, I realized aside from the fact that he was dominating the conversation, I didn’t really have anything to add. He grew up on a farm, and now runs several of his own businesses including building things, selling trees and foliage, and growing crops. That’s all fine and dandy, but I’m a bona fide city girl. While his profession was certainly respectable and profitable, I just didn’t really care. He never really asked anything about me, and anytime I’d get into telling a story he’d find a way to revert back to him and his $30,000 mums. (I knew they were worth $30,000 because he told me no less than eleventy billion times).

On top that, he may as well have been a horny 16-year-old. I couldn’t say anything without him making it sexual. Within ten minutes of being in the pool he came in to kiss me (which is fine, though was a bad kisser with too much tongue, ick), then started go lower. I told him that if he did that again, I was leaving. He started to make me feel really uncomfortable and icky every time he looked at me, but I decided to stick it out, and let him off with a warning. But then when we got out of the pool he got naked and proclaimed, “A preview for later.” I turned around before I could see anything. As I’m recalling these events and typing them out I’m not really sure why I didn’t leave earlier. . . . Oh yeah: He had a boat. Boats are awesome! At the time my friends and I were really looking for a friend with a boat to rock out with during the summer.

So I went to dinner with him, and conversation started to become really painful. I was having trouble hiding my desire to leave right then and there. He continued to talk about how much money he made, and make sexual references, and ask awkward questions like, “Do you have any regrets?” Like, in life? “No, I mean in coming here.” How was I supposed to respond to that?! Then he commented on how many rolls I’d eaten during dinner. A penis-flashing, money-grubbing farm boy who is a carb hater. I pretended I was dog-sitting and had to rush home to let the poor dog out. Sorry, friends . . . couldn’t take one for the team this time!

What’s Spanish for “Disgusting”?

After I first relocated to this area about a year ago for a job, an older coworker suggested several times that I let her set me up with a young relative of hers. I don’t usually let other people try to set me up, but I had heard enough nice things about the girl to give it a shot. We talked on the phone a bit and decided on a nice tapas place. The highlights of the night consisted of her complaining about her family, going through an entire pitcher of sangria by herself in about 30 minutes, projectile vomiting all over the table and our food, and then crying about her dress. It was basically the worst evening of my dating life. I still tried to be a gentleman, though. I paid for the food, tipped the waiter more than my bill since I knew he would probably have to clean that mess up, bought her a cab home, and wished her the best. To this day I will not go back to that restaurant.

The Good Old Days

I went on a date with a guy in high school who had five of his guy friends meet us at dinner and made me pay for my own food at McDonald’s before we went to the movies, where he talked to all of his friends instead of me. Then he took me to an arcade and competitively kept yelling, “Suck that” every time he beat me at a game. He couldn’t understand why I didn’t want to kiss him when he took me home.

Wild Thing

When I was living in New York, I went on a blind date with a seemingly normal gentleman whom I’d met on a dating site. We agreed to meet outside a bar in the East Village. It was warm and raining, which created a mist that was perfect for an attractive stranger to emerge from. Except said stranger was wearing a full-body teal rain suit reminiscent of the ensembles on Deadliest Catch. He never disrobed from the waterproof ensemble at the bar, and I was charitably thinking that he could be cold, when conversation turned to books. His only subjects of interest: “wolf packs” and Christianity. I excused myself when he started to growl—very lupine-like—at the waitress. Needless to say, I declined the offer to go back to his place and “split a large beer,” afraid he might turn my bones into wind chimes.

When You Should Just Stay In on Valentine’s Day

This isn’t exactly a bad date story, but I was working as a waitress on Valentine’s Day when I was 18. I walked into the kitchen, saw some live lobsters, and came out squealing with horror. Five minutes later, one (male) manager summoned me to come talk with him by the bar with a weird look on his face. I had no idea what was going on until he grabbed my hands and pulled them behind my back while the other (male) manager came up with two live lobsters and put them up against my hair. They were squirming and scratching, I had my first ever panic attack and had to be sent home and medicated, the restaurant was a waitress down on its busiest night of the year, and I developed a phobia of crustaceans that persists to this day and means I’ll never be able to enjoy eating crabs. Oh, and I also realized men are a**holes.

Then there was the time a guy I was casually seeing wanted to go to the movies on V-Day. I bought the tickets, he made me a mixtape (one I later realized he’d made for a previous girlfriend and just burned onto a disc for me), and then he made me drive him an hour home at the end of it because he had to “study.”

I have also been broken up with on Valentine’s Day but with a guy who broke up with me so frequently I don’t think we spent more than three weeks together over a year of on-off dating. He broke up with me the same way he usually did—by making plans to meet up and then ignoring all my texts and calls.

Then there was the year when I finally had a boyfriend, now my husband. To be nice, he booked me a hair appointment in Georgetown, and this French woman cut off all my hair and gave me hideous layers that were three inches long, and I cried and cried and cried. And my horrified boyfriend filled the house with flowers to make up for it, but I yelled at him because they were all different colors and the combination of purple and yellow was stressing me out.

So, in short, I hate Valentine’s Day.