Fact: Dating can be totally awkward and uncomfortable. Most of us have had to content with classic offenders like the bad-breath kisser, the cheapskate and the workaholic. But, read the following painful, true and totally hilarious dating disasters and you'll instantly feel better about your own not-so-great encounters.Then leave a comment sharing your own story of the worst date ever -- we may just make it one of our Relationship Whoas.
Dates Gone Horribly Wrong
"I was pretty excited when a guy I met through a mutual friend asked me out. He was cute, had a good job, and we really seemed to click. He told me he wanted to pick the place and was thrilled because I had been out with a lot of guys who didn't take any initiative. He picked a pricey restaurant and when I showed up he had already ordered a bottle of wine for us to split (a really expensive one!). I thought these were both good signs. He then ordered the priciest stuff on the menu. I was a little more modest because I didn't want him to have to shell out too much for me. When the check came he looked at the bill and said 'Do you want to give me your card so we can split this?' I was shocked. He ordered way more and I always figured that if a guy asks you out, he should pay. I gave him my card instead of making a scene but walked out after that." -- Elizabeth, 32
feministjulie, Flickr
"I go to the same deli every day for lunch and chatting with a guy who works in the same area and is always there at the same time. Eventually, he asked me out. I met him on Saturday night for a drink at a really hip bar. We had awesome chemistry and at one point he was stroking my hand as we talked. Out of nowhere, I felt a drink splash in my face. I looked to the side and saw some girl standing there screaming at him. She said he had dumped her without and explanation and then called me a whore. He tried to apologize, but I wanted no part of the drama." -- Ann, 25
Jill Greenseth, Flickr
"I was out one night and conjured up the courage to ask this really cute guy out. He agreed and we exchanged numbers. A few days later I called and suggested he meet me at this outdoor wine bar that I live near. We met up and he already seemed a bit tipsy. I rolled with it and we ordered a bottle of wine. By the time I had finished one glass, he had finished the rest. After that, I was ready to go, but he ordered another bottle- which he also drank himself. After listening to him slur his words for a bit, I insisted on going home. He stood up to walk me out and abruptly ran over to a planter. He threw up everywhere. I was so mortified because everyone was shooting me dirty looks like it was my fault." -- Erin, 24
YoHandy, Flickr
"I rarely let people set me up, but when a coworker said she knew a hot foreign guy I would love, I agreed. The guy was from Turkey and sounded really hot on the phone. We met up at a café to grab some coffee and I was a little thrown-off by his look. He was dressed in really tight, loud clothes and his hair had about a gallon of gel in it. That wasn't even the worst part, his eyebrows where plucked and penciled in. I decided to get past the looks thing and make the best of it. We were joking and having a good time when he said 'I'm surprised, most women won't go out with me once they find out I'm married." I almost fell out of my chair. He then went on to explain that he was married and lived with his wife, but that it wasn't a love match. He had paid some woman to marry him so he could get his green card. When he explained that he would have to stay married to her for a few more years, I knew we weren't meant to be." -- Jessica, 35
chikache, Flickr
"I know you're never supposed to talk about exes on a date, but somehow this man I had just started dating and I got into it. I started describing the ass that I had dated a few months back. The new guy asked me what had made him so terrible and I explained that he was in and band and totally cocky. I went into detail about a few other things, including his small penis. The new guy asked me his band name. When I told him, he glared at me, said that was his cousin, who also happened to be his best friend. We didn't go on a second date." -- Theresa, 29
Riru, Flickr
"I go to the gym semi-frequently but am not a fitness buff. One afternoon, I was jogging and a personal trainer started hitting on me. He was really cute and had an awesome body, so I agreed to go out with him. He took me to a new bistro that had opened up in town. I ordered first and asked for a cheeseburger and fries. He ordered a salad, with dressing on the side, and a chicken breast that wasn't cooked in oil. When the food came, he spent the entire time telling me why I shouldn't eat was I was eating and giving me exercise tips to get rid of my 'problem areas.' I left the dating hating him and feeling totally crappy about myself." -- Erica, 27
chotda, Flickr
"I had been out with this guy a few times when he suggested we meet two of his friends to play doubles tennis. It sounded fun, so I agreed. I'm not fantastic at the game, but can manage. The game got off to a good start and we were winning. But things quickly turned around and the friends were in the lead. That's when my guy started tweaking out. Anytime I would miss he would literally scream and veins would pop out of his head. I honestly thought he was going to have a heart attack. He got so worked up that a small crowd of strangers started to form around the court. At one point, after he messed up, he started beating his own head with his racket. It was terrifying. After that I didn't return his calls." -- Susan, 29
Getty Images
"I was casually seeing this guy and decided to bring him to a friend's housewarming. I had been single for a while and all my friends were pumped that I had re-entered the dating world. The guy, Steve, was really charismatic and I was sure they would love him. At first, he seemed to really hit it off with everyone. A few hours in to the party, I lost track of him. Suddenly, I heard screaming coming from the bathroom. I went to see what was going on and my best friend was cursing Steve out. He had followed her in and tried to make out with her. I was just glad my guy friends were around to kick him out." -- Angela, 26
Scented_mirror, Flickr
"I'm a member of an online dating site and had been emailing back and forth with a guy I met on it. He told me he loved animals, liked to ski, and was in sales. He sounded cool, so I agreed to meet him for a drink. When I showed up, he actually looked cuter than the pictures I had seen, which was a total bonus. To get the conversation started, I decided to stick to a safe topic- his job. I asked what kind of sales he was in. He launched into this whole pitch about how he sells cemetery plots. I was a little skeeved out, but dealt with it. But then he started trying to sell me one! I was floored. I told him I had no intention of dying any time soon and she started rattling off these morbid death statistics and told me I should really plan for the worst by purchasing a plot from him. I quickly made up a lie about having to meet other friends and never returned his emails after that." -- Sara, 31
runnx, Flickr
"A guy that works for my company, but in a different department, asked me out and I agreed. We decided to grab a low-key dinner to see if we clicked. Almost immediately I knew we were not going to work out. Before we even ordered a drink, he asked me what my bra size was and explained that he really didn't like dating anyone under a C-cup but couldn't quite figure out what I was. I tried to laugh it off and change the subject but then he asked me what my favorite position was. I tried to gently tell him he was being inappropriate but he wouldn't catch on. The final straw was when he asked me if I would consider a threesome because he already had one girl lined up and needed another. I didn't even say goodbye, I just grabbed my purse and left. Now, I do everything I can to avoid him at work." -- Larissa, 28
PiperKins, Flickr
















