Bad dates–we've all been there, right? Sometimes things get to a restraining order level of heinousness, and it's even worse when the other party seems to think it all went hunky-dory. In an attempt to make you feel more comfortable about sharing your horror stories, I've taken a moment to detail the worst date of my life. Spoiler alert: I slept with him.
– Dewitt
Photo credit: Flickr
To read my terrible dating story, follow the JUMP:
It all began at a bar in New Brunswick, NJ called The Den. I had just broken up with my boyfriend, and it was the perfect spot for drowning in my sorrows with the friendly bartenders, unattractive men who'd buy me free drinks and the occasional cute college boy from Rutgers.
After arriving and equipping myself with a beer, I moved on to the dance floor area. Two men were gyrating with themselves in the mirror to a bad Britney remix, and I wasn't very impressed until I saw an adorable guy sitting on a couch in the corner. He was a scruffy lad who vaguely resembled Lee Pace of Pushing Daisies and Wonderfalls. Being my socially awkward self, I had no idea how to approach him.
Feeling defeated, I went back to the bar and chatted with a nearly seven foot-tall black man. I liked to refer to him as my fairy godfather, though my friend would later give him the politically incorrect titles of my "own personal Kazaam". He encouraged me to man-up and speak with my corner-crush, while simultaneously hitting on me in the most blatant fashion.
It only took a mere shot or two of "confidence" to drive me towards that couch. I sat awkwardly for a few minutes and then we eventually traded some awkward banter. At the time, he seems douchey and insulting in a cute way. My desire to punch him just gave me an excuse to touch him.
And then we made out. This was done mostly in his car, while listening to his favorite band Tegan & Sara. He confessed that he had the musical taste of a lesbian… and that he was a total bottom. What? Well, that was awfully forward and inappropriate of him. And yet it gave me a total boner. With a few more sloppy kisses, we made plans to go on a date after I moved to New York. I would have never guessed that I'd be agreeing to the worst date of my life.
The sequence of events remains pretty hazey. I believe our first venture was to a hotel, but get your mind out of the gutter! We were actually picking up his lesbian friend, who'd apparently be joining us for the evening. She was busy or something, so he demanded against the will of my thin pockets that we take a cab down to Christopher Street. Let's break it up by venue…
Some random cafe: This was apparently his favorite restaurant ever, which evidently proved that he had no taste buds. During our meal, he told me that I should get contacts, shave my beard and cut my hair shorter. He also confessed his obsession with Asian men and uttered the phrase, "Could you fuck my love of Asian men out of me?"
Pieces (gay bar): It's karaoke night with a particularly obnoxious drag queen hostess. My date contemplates leaving me for some guy who performs 4 Non Blondes' "What's Up?" He also tells me about another guy who's checking him out, just to point out how attractive he is.
The Cubbyhole (lesbian bar): This is where we're supposedly meeting his friend, who is now over an hour late. Drinks are consumed, as I wonder why I'm still on this date. It occurs to me that I am fragile after the break-up and hoping for some rebound sex. Everything is bearable at this location until I overestimate the strength of a table and knock over the drinks of some butch dykes. Sensing danger and shattered glass, we flee the scene in embarrassment.
The Duplex (gay bar): Nothing much happened here, aside from more insults and drinking.
Ty's (gay bar for bears): It was a cold night and the other bars were too crowded, so my date suggested we go here for some space and warmth. He proceeds to make comments about how everyone at the bar is probably HIV-positive and asks me to stick my hands down his pants to finger him. I proceed to wonder about the relationship status of the cute cubby guy in the corner.
The Cubbyhole (again): Finally! It's nearly two or three hours later, and his lesbian friend is ready to meet us. She shows up with two strangers–a 25 year-old reptilian bisexual and a 16 year-old boy. Both of them have just been released from police custody, and she decided to invite them out after meeting them on the subway. Since the bar is checking IDs and she isn't twenty-one herself, we had to head elsewhere. Along the way, he asks again for me to stick my hands down his pants and finger him. Since my hands are cold and he has a cute butt, I accept the offer.
Julius (gay bar): This historic bar dates back to the Stonewall riots, as did some of their clientele that night. Now I'm not complaining about this, but there were some creepy interactions between the sixteen year-old and a mature gentleman. After our two new "friends" showed us the drug pockets in their jackets, I felt a need to play erotic photo hunt on one of the bar's touch screens. When I am lost, I search for the third nipple in a softcore porn pic.
My apartment: Due to some unanticipated subway issues, it wound up taking two hours to get back to my place. I figured I'd take the couch and just let this kid sleep in my bed. What I didn't figure is that he'd strip to his boxers, lie in my bed with them pulled down slightly and talk about how horny he was. This is when I realized that I have no post-break-up dignity or standards. After all the shit he talked, I couldn't resist that round, hairy goodness.
The sex: As far as I can remember, no blowjobs, kissing or foreplay occurred. It was all about his ass. He didn't want it to be fingered. He didn't want it to be licked. All he wanted was for me to put a condom on and fuck him hard. It was five in the morning by now, so I couldn't even grasp how unsexy this was. We got to business and as I started to pound away, he pulled me out and told me I wasn't a very good top. Then he requested that I cum on his asshole and finger it in. We made a compromise that I'd cum on his chest, and let's just say that I felt a need to get tested afterwards (just in case).
I made a vow that I'd never talk to this man ever again. The Facebook pictures his lesbian friend posted were immediately de-tagged. I received a message asking when we'd be hanging out again, and broke my vow to tell him that I wasn't interested in seeing him again. He replied, "lol, whatever man. i thought we were just having fun." Think again, my worst date ever. Think again.
Wow O_o that’s extremely shitty
wow thats horrible. I was going to tell my story about my date with a guy I met offline. We went to dinner and he proceeded to tell me how unattractive he was and how he doesnt date alot because he doesnt fit the “gay stereotype” of what gay men should look like. Really akward. I just said well who does man? I thought it would make a good debate but it didnt.
After the akward dinner, where he told me he doesnt like to talk while eating. (?)
He offered to drive to a local bar for a drink. Which I needed after that dinner.
On the way he tells me he is OCD and during the story he runs a stop sign and almost hits a van!
Scared shitless for my life, he blames me for talking to him while he was driving.
After the ONE drink I said it was good meeting him and said it was a nice night for me to walk back to my car. It was only 5 blocks.
He sent me an email shortly after and I said I wasnt ready to date and I wasnt interested in seeing him again.
It was the worst and most socially akward date I have ever been on.
But that date above was horribe too. I would not have fucked him or fingered him!
He sounds like a bitch. fuck that
good story though!
My worst date was with a flight attendant I met who was staying over in Portland. He was sort of cute that Friday night, but in hindsight, I think it was the bar lighting and the alcohol consumption that increased the attraction. He asked me to dinner the following evening. I picked him up, because he was just staying the weekend at his hotel. He walked up to meet me in the lobby, and was literally wearing this large rhinestone brooch, pinned to this purple flowy shirt that could have passed for a dress. I steeled myself up for dinner, which amounted his retelling of wonderful trips to places like Sioux Falls, Omaha, and other dreary places in the Midwest. Finally, I said I wasn’t feeling well, which was only a half-truth, as I could smell his breath across the table. The waiter came by and asked if I would like to take the remaining 1/3 of my pasta dish, I told him “No”, and my date said, “Well, that’s rude if I”m buying you dinner to waste it.” So, he got a to-go container, and took the rest of my dinner. Then he asked if he could come home with me. I told him no, and let him find a cab to his hotel. Ugh.
That was an awful date. The worst date I have ever been on was with a blind date. He picked me up at school and we headed off to a destination an hour away. He had a nice body, but his personality and teeth were lacking. He told me we were going to a dance. Ok… sounds cool. So when we got past the point of no return (a.k.a. the point where it would be longer to turn around and go home) I asked him what this date was for. He then proceeded to tell me that the dance was sponsored by Alcoholics Anonymous and we were going to the meeting before. He then told me that I was taking this well. It’s not like I could have run away! So we get to the meeting late and people keep asking me what step I was in the program. I kept telling them I was not an alcoholic, which made me sound more like an alcoholic. I then found out about his crystal meth addiction and how that landed him in rehab for 17 months. I wanted to find the eject button for this date. We danced and he took me home. And when he leaned in to kiss me, I leaned in and gave him a big hug. I never saw him again.
I don’t know what is worst – the date or the fact that you stayed on the date for so long. I would have gone home or found something better after the comment about fucking his love for Asians out of him. 🙂
But yeah, that ranks up there as a really bad date. He sounds like a total douche!
Shortly after the end of an 11 yr relationship, it was for New Years Eve. I had a date that cancelled at the last minute. The one thing that I knew is that I didn’t want to spend NYE alone.
In desperation I turned to Craigs List and was going to post. Here was a post from what sounded like a really nice guy who was new to the area and like me didn’t want to spend the evening alone.
We chatted several times in the next 48 hours and exchanged pics. I bought champagne, and made a light dinner, and we planned a casual evening at home. Neither of us wanting to drink and drive on the crazy holiday night.
He showed up an hour late, 10 years older and 30 pounds heavier than he appeared in his pics, dressed in ragged jeans and a tshirt with holes in it…
He brought his dog, that he had just rescued from the pound the day before.
He couldn’t hold a conversation. After about an hour and a half or awkward conversation, it was getting close to midnight and he said, “Hey how about if I blow you and you cum at the stroke of midnight?”
That was the best idea I’d hear all night, so agreed. Hell I had to have something good to remember about my first NYE single.
We did as planned and before I even had my pants back up he was up, and had his dog, at the door asked me for gas money for his 20 minute trip back home…
i don’t mean to L.O.L., dewitt, but i am going to have to L.O.L. at that horror story.
see, things like what you described above is what makes me not want to go on “dates.”
i really am surprised that i don’t just keep myself locked inside my house, where it’s relatively-safer from all the riff-raff.
(i don’t imagine this “dream guy” left your Fingering-finger smelling spring fresh, after his requests…)
(i admire the proudness with which The Naked Italian has himself on display, by the way.
{his Stocky Friend could not be anymore mortified, however.})
that’s what you get for going to the den! haha. the ultimate cesspool of gay carnal connections..
SORRY DUDE, YOU LOST ME AT THE DEN…NUF SAID!!