Written By: Mackenzie Newcomb
I’ve had my share of bad dates, including one that ended in “you and me, we will never workout, but we should be sex friends” (although honestly that might not even have been the worst.) I asked my readers to tell me about THEIR worst date ever, and the responses were awesome. If you think you have either a terrible date story or an awkward hookup story, be sure to submit them.
1.) A guy picked me up at my house for a movie date when I was a sophomore. We were meeting my friend and her date there. He showed up sunburnt and shit-faced with beer in hand(while driving). We got there, he makes us see Terminator, and proceeds to yell at the screen in between passing out. At one point he excuses himself to the restroom only to come back announcing to basically the entire theatre a very loud graphic shit he witnessed taken by another movie goer. After the movie, he asked me if my friend’s was retarded (actually meant it) AND sang torn by Natalie Imbruglia the whole way home.
2.) I was set up once with a family friend’s nephew who I was told was in a band. I thought that fact made the guy seem pretty cool so I agreed to a blind date. About an hour before the date, I got a text about how this guy had to go to an emergency youth group meeting and if I didn’t mind going, we could go to dinner after. Of course I agreed because I’m way too nice. So I ended up in a youth group meeting, where the leader was this guy’s dad – awkward moment number one. I also ended up finding out my blind date’s band was actually a screamo Christian rock band. After an hour of listening to the true meaning of love, the subject of the meeting since it was close to valentines day, which made the whole situation even more awkward, I was ready to go home. I texted my mom to pick me up and thanked her repeatedly for never subjecting me to youth group and for saving me from the date from hell.
3.) She was snobby, crazy and didn’t appreciate my style. I made her pay.
4.) I had a guy I was seeing come visit me at school sophomore year and we decided to get fro yo. He made me pay because “he had to pay for gas” and when we were done he kissed me by the dumpster and pretended to throw me in it.
5.) My first (and last ever) tinder date was without a doubt the worst date I’ve ever been on. I match with this kid and after a few days of harmless flirting he tells me he wants to take me on a nice date. It was restaurant week on the vineyard so he finds a super fancy place and makes a reservation. When the day comes he picks me up and shakes my hand when he introduces himself to me. As were driving and making small talk, he admits to me that he’s been drinking all day and is a little buzzed (strike 1). The dinner itself went decently, but when the $138 check came to the table he looks at me and says “wanna split it?” (strike two. Don’t take me to an expensive place on a first date and expect me to pay. I’m not a Rockefeller). He begrudgingly pays and we leave. As were driving home he decides he wants to show me where Barbra Walters lives, incase you didn’t know it’s down a sketchy dirt road that’s 3 miles long. We get to the end of the road and he points to the driveway and goes “yeah she lives down there”. He then pulls the car into a makeshift parking spit and puts it in park. While this is all happening I texted my best friend and had her call me to tell me she’s sick, which she ever so wonderfully did. We pulled out of the spot and he rudely proclaims “didn’t even pay for dinner and you’re cutting our date short.. Jesus.” (Strike three). We finally arrive home and I jump out of the car and run in the house. Jump forward 3 days and several ignored texts later, I’m at a bar with my friends and he marches right up to me. I exchange awkward pleasantries with him and leave. As I’m walking out I get a text reading “you don’t have to fake it you know…” His numbers now been deleted and blocked. Long story short; when someone asks if you want to see Barbra Walters house, say no.
6.) He pinched my side when I told him I had to wear tight shirts to work… and said “just making sure you could pull that off.” And then proceeded to come back from the bathroom with a white “powder” under his nose.
7.) So, this was a Tinder date. I met up with this kid to see his friend’s band play at a local bar. When I showed up, as soon as I saw him, I knew I wanted to gtfo. He was way shorter and uglier in person and super awkward. So this bar is basically empty except for his friends and the band. He’s pretty drunk and puts his arm around me and I’m obviously so uncomfortable. His band starts playing and it’s a band without a singer so I’m listening to interlude music while also dying on the inside because this guy is groping me. He obviously thinks the date is going well because he starts kissing me on the cheek. Then I’m trying to avoid looking at him and he blows on me. HE BLOWS ON ME. I’m obviously not going to turn my face towards his. About an hour of this goes by and I finally find the opportunity to duck. And have avoided his texts ever since.
8.) I was a freshman in high school so I had never been on an “official date.” In fact, I still wonder if he considered it a date? Anyway….I had a HUGE crush on my friend who was a senior and one day he asked me to hangout after school. We decided Buffalo Wild Wings was the move (how romantic). I was so nervous about looking like a hot mess while eating the wings (no pun intended) so I ordered a salad. He, on the other hand, opted for the “diablo” wings just to try them out. By his second wing there were tears flowing down his face, a pool of sweat forming under the arms of his Hollister sweatshirt, and his eyes were glassier than Snoop Dogg’s. I was so overwhelmingly uncomfortable that I asked him if he wanted a bite of my salad, but he could not form the words be needed to. Seeing his was in obvious pain, the waitress brought over water, bread, and sugar to soothe the poor kid’s taste buds. After 10 minutes of these remedies, he seemed to be out of hell. I couldn’t bear to see him reach for another hot wing so I told him I had to be home. The moral of the story is, if he’s cryin on the first date, there probably won’t be a second. …At least he paid.
9.) A few years ago my boyfriend at the time and I had planned a nice date night in. We were going to make dinner and watch movies, cute couple things. However when I got to his house I walked in to see his ex on top of him on his couch. Not only was I pissed off but we then had to bring her home. Instead of dinner and a movie he spent the night trying to explain what was going on. It ended up with things being thrown and me walking home. I let him try to explain himself the next day, but what I got from his ex was he wasn’t expecting me for an hour, and they had been “talking” a few times a week trying to “figure stuff out”. Let’s just say he was soon single and could “talk” to anyone he wanted.
10.) So, I had a class with this guy in the fall semester of 2012. He was really weird, and I had no interest in him at all really. He asked me out to dinner, and I didn’t want to say no and hurt his feelings so I said yes to be nice. I decided to drive myself there, and thank God I did. Within the first five minutes, he downed two wicked big beers. He claimed that it was “to calm the nerves”. It took him forty five minutes just to choose his entree, which he later told me that the reason for that was the boner he had the whole time… At the end of the night, we walked out to the parking lot where he forced a kiss on me and shoved his tongue down my throat in the process. I pushed him off off me, said I was leaving and then washed my mouth out with mouthwash as soon as I got home. Never again.
11.) It was the first “official” date between me and my then-fix–an aspiring investment banker and frat star extraordinaire. He takes me to an impressive but obscenely overpriced steakhouse downtown, where all of my energy is expended forcing a coy smile while my seven-years-strong vegetarian self internally cries out for help (or at least a Cliff bar). Deciding that it was best to be an expensive date than risk looking like an anorexic, I order the $32 mac ‘n cheese. He out-does me by ordering the chef’s choice. In attempts to drown out the seemingly endless “stories” of how his golf game is at it’s peak or about his upcoming trip with the boys to Tahoe, I order a glass of wine. He proceeds to drink six (yes, six!) craft brews. We top off the meal with an array of fancy desserts, while he forcefully draws the comparission to his chic hometown country club (as opposed to the one his parents bought him into at college). Just as I began to seriously considered scaling down the pier and testing my swimming skills in the river, I spotted the waiter bringing the check. The end was in sight to my relief, or at least so I thought… He winks at me and reaches into his back pocket to grab his card, only to release he left his wallet at home in his work slacks. I begrudgingly pick up the tab, which needless to say, cost more than the Wang bag I got at last year’s sample sale. He never called me again.
12.) I met the girl online on POF. We exchanged messages, lived only a town away and had some common interests so naturally decided to hang out. When I go and pick her up I realized that she was not the girl in the pictures she had posted…. uhh…????? (she wasn’t UGLY in person, but I wouldnt have been as inclined to meet up with her). So not wanting to hurt her feelings after her trying to explain herself, I decide to go out with her anyway, at least we had some common interests. Turns out she made up all of those interests as well. I bought her one drink, and she bought herself 3 more while I drank water… awkward.
13.) I went on a blind date and arranged to pick up this girl in Boston. When I picked her up, she was just getting out of work at a vet clinic. She smelled of wet dog and threw all of her dog scented clothes on my back seat. She obviously used angles on her facebook page because she was an entirely different looking person, not for the better. She asked, “Do I smell like dog?” and proceeded to take out my air freshener and rub her neck with it. I CANT MAKE THIS SHIT UP. I’m a gentleman, so I still took her to the movies, where she repeatedly tried to move in for a kiss. I refused as nonchalantly as I could muster and drover her home afterwards, where she asked if I wanted to meet her mom. She still hits me up to this day, to try and meet up and politely refuse to this day. Worst date ever.
14.) I had been talking to this guy that I went to high school with and he told me he wanted to take me out for dinner and a movie. Instead, he sends me a text at 3 pm (an hour before the movie starts), brings me for ice cream that we ate in his car, admitted that he hated the movie we were about to watch, and asked my opinion on abortion (which we disagreed on, by the way). I was home before dark and I never ate dinner that night.
15.) A guy said he wanted to take me out for dinner… He ended up taking me to a takeout place, ordered food– which I thought was for the both of us – then he paid for it and then when we sat down he started eating it and said why didn’t you get anything? …………ohh okay.
16.) I went on a blind date where the guy took me to Taco Bell and then the arcade to play air hockey for a kiss. I’m fine with this as something to do with a boyfriend, but not a first date.
17.) One time this girl asked me out on a date to go see a movie. She ended up picking Black Swan….it was awkward to say the least.
18.) I met this guy through a mutual friend and we hit it off. He was kind of chubby but had a cute face. I’m not usually one for the chubby guys but I gave him a shot. I invited him to come out with a group of friends and some of my cousins as well. One drink turned into 2 and 2 to 3 and so on. Everything was great, we danced and laughed and the whole nine yards. At the end of the night, the designated driver was driving us back to my aunts when I got a bit dizzy and yacked all over his shorts in the back seat. It was so bad that my uncle had to give him an extra pair of shorts. Then he tucked me in and left. To my surprise, he wanted to hang out again, but I didn’t. He blew up my phone for months before he got the hint…
View all articles by Jason Olephant
I might actually have a worse story. A year ago, this guy showed up a half an hour late to the date without a shirt on. He explained to me that he was late because he was fighting with his ex, whom he was still living with, while he looked for a shirt in the back of his car. Then he spent the whole dinner complaining about, not just his ex, but every ex he has had, and how they all seem normal at first but somehow turn into crazy bitches after dating him.
A couple months ago, I saw this guy at a party, and, against my better judgement, decided to talk to him because “he might have changed”. We saw eachother for two months and had an awesome time. Then I told him I would be down for an open relationship and he started doing drugs again. He started introducing me to different random girls he was sleeping with (none of whom stuck around), was trying to get me in bed with them (but they were all straight), and trying to act like a pimp. However, if I were to even touch another guy he would freak out. I made up my mind to dump him while he was telling me about our marriage plans.