Ugh! Dating. Am I right?! It’s like sometimes you meet people and you think they’re really hot or funny and then you go out on a date (outside of the bar or Internet) and all of a sudden they’re really boring gropers who love to talk about how fast they could run in high school. But then again, if you’re lucky, sometimes it works out because neither one of you barfs or text-fights with your ex during dinner. So, because this is our Valentine’s Day issue, we’ve collected a few dating war stories to remind those of you in relationships how much dating sucks and those who are still single that we feel your pain. Enjoy.
Overbooked and Underwhelmed
I went out with a big group of friends last year on Valentine's Day to a nice Italian restaurant. When we got there, even though we had reservations, the place was overbooked and we ended up waiting an hour at the bar for a table. Once we were finally seated, our waitress came over and told “Bert,” the guy I kinda liked and was paired up with, that since we had to wait so long she would be giving us free Prosecco on the sly (obviously to make sure she still got a tip considering how long we waited). Well, Bert ended up drinking a ton of Prosecco and by the end of the meal he not so suavely told the waitress he would love to pour some all over her. We haven't talked since. — Ellen
After months of teasing and taunting, this boy finally seduced me to come back to his place to enjoy all the pleasures of, well, the obvious and then he promised a day-after of sleeping in, lounging and doing whatever else you do in a mansion, which is what he claimed to live in. After driving for what seemed like a lifetime, we got to a less than humble home. Between make outs in the front lawn, we finally made it to the front door where I could see the light of a TV. This was interesting because there was never mention of a roommate. As he fumbled to unlock the door, he confessed, "Oh, I have a roommate." Totally cool with me until we walked in and I realized his roommate, who was watching People’s Court at 3 a.m., was in fact his mother and this so called “mansion” was in fact the home he grew up in. With no introduction to his mom, she announced she was just about to go to bed and then we all together, single file went up the stairs. — Anonymous
His name was Keath. Keath like Heath. When he asked me out he was wearing a baseball cap. But when he picked me up for his Catholic high school homecoming dance, he was hatless ... and he had the absolute stupidest hair I'd ever seen! A middle-parted bowl cut with frosted tips and about five inches of horizontal volume. And a night-and-day tan line dividing his forehead where the cap usually stayed put. On our way to the dance in his half-totaled Saturn, he blared Insane Clown Posse and tried to get me to play “Strip Padiddle.” At the dance he lifted my taffeta skirt in front of everyone, had a banana in his pocket when he slow-danced with me, snuck a flask into the bathroom, passed out next to the urinal and was dragged out of the cafeteria by two nuns.
After Hours Excursion
On a date with my now current girlfriend, we concluded a night of bar-hopping in Northside and went back to my place in Brighton. When we got to Brighton there was a huge party going on at the Mockbee. We were surprised because we hadn’t heard of anything going on at the Mockbee that night and walked over to see if we could get more drinks since it was after last call. When we got to the front door there were two black gentlemen walking next to us heading to the same party. We asked if they knew what was going on at the Mockbee tonight to which they replied, "Oh, It's a Gay Black Party." We thought this sounded fun and went inside with them. The place was packed with hundreds of people. After dodging a fight on the back stairs, we got to the main floor area where drinks would have been served. The dance floor was stuffed to the gills with people. There was nowhere to move at all. As soon as we squeezed into the room, another fight broke out, which caused a stampede to exit the room. A chair was thrown onto the person that I guess was losing the fight. But I have no idea where a chair came from since it was standing room only. We decided to head out since the police were showing up and had blocked off Central Parkway. — Mike
Creepy Charming Charlie
Back when I was romantic and skinny, I would give cutesy notes to attractive girls I would see at college. I gave this one specific girl a Valentine's Day card with two types of chocolates, milk and dark, attached. We started chatting and ended up talking for hours. I kept a journal during our four-hour phone calls and wrote down what her favorite ice cream and flowers were. Finally the big night came, our first date. I arrived with a handful of lilies and, to score extra points, some freshly baked chocolate chip cookies I had made. I took her to a fancy dinner at the Olive Garden and arranged for us to go to a park on the riverfront afterward. I pulled out a cooler I had prepared earlier in the day from the trunk of my car; it contained her favorite ice cream, peppermint. We stared at the city’s skyline chatting all night long. The date continued until the afternoon of the next day. It was the best date ever! Especially cause I thought Olive Garden was classy. — Charlie
So I was hanging out with this girl for about a week. Just casual hangout type stuff. I really liked her so the next time I saw her I proposed, “Hey, it’s about time we go on a real date." She agreed and I was psyched. I suggested a movie. "I heard there's this new bad ass vampire movie that just came out, it’s called Twilight." Needless to say, I had no clue what I was getting into. She hadn't heard of it, but agreed to see it anyway. We went and saw it, and embarrassment ensued. After several apologies and more embarrassment, somehow I still managed to end up in her bed at the end of the night. Then when were fooling around she asked, "What would you do if I took my clothes off right now." My repose was "Yeah, I'd probably leave." I was just kidding but she didn’t get it. :(. — Anonymous
Second Date, Fourth Meal
I went on a couple dates with this girl a few years ago. I don’t even remember where I met her, only that she liked going to Taco Bell late night. This was back before Taco Bell even made up the “Fourth Meal” advertising campaign. Maybe it’s what led to it, though. I can’t really say. So anyway, we were supposed to go see Bringing Down the House starring Steve Martin and Queen Latifah, and I just really didn’t want to go to Taco Bell afterward (I had already eaten there once that week). The movie was a lot better than I expected, but I expected it to be terrible so that might not be saying much. We ended up going to Taco Bell that night so that was our last date. — Danny
So I was in high school and I was going steady with this girl from another high school and Valentine’s Day came up. I was young and I didn’t realize how weird girls were about Valentine’s Day. I told this girl I couldn’t see her on Valentine’s Day because I was getting my hair cut. I couldn’t drive yet and I wasn’t paying for my haircut because it was a three-for-one deal or something so I had to go with my mom, otherwise it’d be like three more months before I could go again. So I told her I wouldn’t be able to do anything that day, but the day after Valentine’s Day we could do something. Well, for some reason she thought that was me setting her up for this really awesome surprise. So I get this call at 11 p.m./midnight from her and she starts flipping out talking about how I can’t make time for her so she told me we shouldn’t be together. I thought, OK, we’re broken up and then I went downstairs and gave my mom the Valentine’s Day gift I had bought for the girl. Then, the next day, I went down to the locker room of my private catholic school and there was the girl, which was weird because she didn’t go to my school. It was like crazy behavior. She said she couldn’t stand being apart and offered to give me a ride home to talk. She could drive which was badass because I didn’t. So she drove me back to my house and said she got me these really nice Valentine’s Day presents and she wanted to give them to me. I told her I think I gave your Valentine’s Day gift to my mom and I don’t think we should get back together. Then I shut the door. Ever since then I’ve gotten amazing things for girls, like giant pinwheels. — Stuart