Tuesday, June 29, 2010


After my breakup, I really wasn't in the market to be actively dating. (Especially after a very awkward situation I created while attempting to date this guy at my part-time job which may or may not have led to me slightly stalking him & my ex-gf leaving him a very drunken voicemail rambling on about his cock.) So imagine my surprise when one summer I scored 2 dates in the course of 72 hours - not even trying! So hey, when life gives you lemons, might as well date both of them at once.

The first came when I was waiting at the train station on my way home after work. A guy came over and asked me when the next train to Stamford was and I told him 6:08. He asked if I was waiting for the same train. (I mean, come on, obviously I was - No, I just hang out at random train stations.) So he starts chatting me up, asking me if I'm from the area. I told him I grew up there but I just moved to CT. He told me he did too and went to the local all boys Catholic school where I just so happened to have worked as a counselor for many years. He asked me how old I was: I was 24. He was 34. (From here forward, he is referred to as "The 34 y/o") We continued talking at the station and on the train, since we were both getting off at Stamford. When the train was pulling into the station, he asked for my number and if I wanted to get a drink some time. Pulling out his ancient Nokia cell phone, he punched in my number and I shrugged it off and headed towards my connecting train.

The next day I got home from work early and headed over to some local happy hour spots in CT to try and meet some friends (I was still pretty new to the area). So I downed a few martinis in one restaurant me & my mom like to go to, then headed down to the waterfront to this outdoor bar. As I stood drinking and texting my friend, viewing all the older happy hour patrons, a really cute guy came up and asked if I was waiting for someone. Then, just as quickly as I could reply, he flashes me his wedding ring and turns to point at a table of 2 frumpy guys and tells me one of them wants to buy me a drink. I've got a pretty good buzz going on and hey, who knows, they might be cool, so I go over and hang out with them.

The less frumpy one who had all his hair and was possibly somewhat attractive was the one who had his eye on me; the frumpier, balding, nerdy one was his older brother. They were pretty cool and funny and so I hung out with them, going from the bar to behind the baseball field where they retrieved a Rubbermaid container of Keystone lights from their car (real classy huh!) and we continued to drink. Less Frumpy's (Now being referred to as "LF" for simplicity's sake) friends cleared the way to let him make his move on me, to which I drunkenly obliged and led to some making out and fondling in the back of his friend's car. Afterward LF began walking me home and asked me for my number - I drunkenly responded, "Uhhh, what was your name again?", took his number down in my phone as well, and stumbled home.

LF called me the next day and we went out to dinner (OUTBACK STEAKHOUSE!) and began hanging out more since he was semi-local. (He grew up there but his mother moved recently; Since all his friends still lived there, he'd come down and stay with them on the weekends.) We'd go to the movies, hang out at his friend's place and do Power Hours (Oh yeah, I was living it up.), made him take me to an Anime convention; I pretty much had the kid wrapped around my pinky and could make him do anything for me: The power of my hotness, I suppose. I enjoyed hanging out with him. He was fun and funny and pretty cool. His friends were awesome too. There was just one problem: I was totally not sexually attracted to him. Further confirmed when I finally slept with him 3 months after we'd be hanging out and it was a complete and utter let down.

From that point on I tried to avoid any kind of sexual interaction with him. Unfortunately, he turned around and told me he thought he was in love with me - to which I just smiled. And then, when he told me he loved me again a month later, I lied and said it back because I felt bad. This apparently made us "Facebook Official" with our relationship. Shortly thereafter, I became fed up with his insecurities, clingy behavior and lack of bedroom skills, I abruptly ended the relationship and the timing couldn't have been better; His car broke down, he lost his phone and I stopped talking to him all in one weekend. It could've been the next County hit!


I'll backtrack now to the 34 y/o, since that whole adventure lasted much shorter. He called me a few days after our meeting to arrange a date for that Friday night. I met him out at a nice lounge for drinks and dinner. Unfortunately, I came to find out that he had been living with a woman in Vermont for 2 years and they had broken up and he was living in his friend's spare bedroom - for the past year & a half. He had no car. He worked nights a big corporate television station that shall remain nameless. I had a pretty good time and he invited me back to "his place" (aka his friend's apt that he was sharing) so I said, why not? You only live once. We took the train and a cab to his friend's apt, stopping to get beers along with way, hung out on "his balcony" and compared tattoos. We had started watching "Almost Famous" (his favorite movie), then he decided to show me his guitars (he was also apparently a musician) and then things started getting hot and heavy.

Before I knew it, I was that "sex on the first date" girl. And 5 minutes later, it was over. I figured he was just drunk so really not a big deal and went to sleep. We woke up in the morning and there was another 5 minute romp in the hay which I again attributed to being hungover/morning. So I cabbed it back to the train (which I had to pay for - not too thrilled about that since I don't carry cash & got into a fight with the cab driver because I tried to use my card & he told me I had to call the card in in advance before I got in the cab. So I asked him to stop at an ATM & he takes me to a gas station where the ATM didn't work, then takes me to an actual bank and tries to charge me $3 a stop when his dumb ass should've just taken me to a bank in the first place. I handed him a $20 bill and told him to go fuck himself.)

Not really anticipating going on another date with the 34 y/o again, I begrudgingly agreed to date #2 when he called and said he was going to get a hotel room for us for the evening. (Since you know, he lives with his friend. Kind of awkward to keep bringing chicks back to a place you don't own, I'm sure) Sweet! It's just like "Pretty Woman", I thought. So date #2 commenced - I picked him up, we valeted the car, checked in, and headed to a local bar for drinks. Here's where things went down hill. At the bar, he gets the first round, then TELLS me it's my turn to pay. I would have had no problem offering to pick up the tab. Just don't TELL me I have to like it's my duty. So we go back to the hotel, get some wine/champagne from the lobby and go upstairs and rent a movie on pay-per-view. (Forgetting Sarah Marshall, if you were wondering. Hilarious film, btw.) So we're laughing and drinking and he decides to give me a massage. Which leads to him pouring champagne all over my chest and licking it off. Which leads to sex. Which leads to, 5 minutes later, just as I'm starting to get into it, he's done. And not just that - here is the icing on the cake (literally): He pulls out, pulls the condom off and proceeds to jizz all. over. me. I am just laying there in shock like "WTF??" And also pissed that I will need to wash my hair again in the morning.

So we go to sleep and I try to take a shower and sneak out in the morning so I can get to work and never have to see this guy ever again. When I come out of the shower, he's awoken - and so has his cock - as he pulls back the sheets to show me the "surprise" he has for me. Knowing this won't take long, I get on top and sure enough, 5 min later, it's over and done with. I say goodbye and go downstairs to get my car... Which breaks down 4 blocks away from the hotel, no thanks to my ex's constantly fiddling with it. (And luckily the tow truck driver is a Honda head so he knows exactly what is wrong but unfortunately doesn't have the tools to fix it.) Mind you, as I'm waiting the hour for the tow truck, I am texting the 34 y/o and he doesn't bother to come by and see if I'm ok because he's going back to bed since he doesn't have to work til 1 o'clock. (A very nice, pretty hot ambulance driver did stop and help me push my car out of traffic, hung out with me til the tow came, bought me a water and asked for my number in the meantime though.)

So after my car has been towed and I am trying to reclaim my modesty at home later that afternoon, the 34 y/o texts me to tell me I "forgot something - teehee" (my thong. He could keep it for all I cared.) and then asked if I'd been tested because there was blood on the condom when he went to throw it out. (I thought my period had ended; Guess not. But then again, maybe you shouldn't be having casual sex with girls if you're paranoid about this shit.) I never talked to him again after that, despite a few attempts for him to get in contact with me including one drunken text message where he called me a bitch, and a pathetic voice mail where he "thought we had a good time" and wished I'd call him back. Sorry, Quick Draw. No dice. In the end, I finally blamed his minute man status on the fact that he was so friggin' psyched to be 34 y/o and sleeping with a 24 y/o hot chick that he just couldn't last. He was also balding and had an awful goatee, so I guess it was for the best.


While my relationship with LF was much more interesting and lasted much longer than my brief encounter with the 34 y/o, that certainly was not the last time that I found myself double-dipping in the dating pool. And certainly not my last One Night Stand experience - Those stories to follow...


  1. tee hee

    man I am totally living vicariously through your tragic date fails.

  2. Oh and there are a few more to come. (I was pretty reckless with my vagina there for a bit.)