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I recently read Chelsea Handler’s My Horizontal Life: A Collection of One-Night Stands, and it inspired me to dredge up one of my own romantic disasters to use as fodder for blog content.

One of my few “successful” attempts at online dating was with The Rich Asshole about 4 years ago when I was still living in Brooklyn.  We met via match.com and after exchanging a few emails we met up for dinner. He seemed nervous at first, which I found amusing because usually I’m the one shitting myself around potential suitors.  I immediately liked him because he was on the beefy (but not obese) side and was attractive but not more than me. My shallowness aside he was also intelligent and had a sense of humour I could get along with (i.e. he laughed at my jokes and even made some good ones of his own). At the time I might have used the word “sweet” to describe him because at the time I didn’t realize I was a sucker for assholes (no pun intended).  I later discovered that he had recently lost quite a bit of weight and still had some insecurities about his appearance.  So for the course of that evening anyway I was feeling quite good about myself but, in retrospect, should have savoured those few hours of having the upper hand.

Dinner went well and, despite telling myself that I wasn’t going to ruin the potential of this date by being a whore, we decided to go back to his place after a dozen or so drinks. During dinner I had picked up on the fact that he was well-off financially and always had been. He had attended a well known prep school and an ivy league university and now worked for one of those financial companies that is busy ruining the world. So imagine my confusion when we got back to “his place” to discover that he was renting a room from a married couple who had children. And not in a subtle “room down the hall” way. It was a bedroom right next to their dining room and kitchen.  Apparently they spent a lot of time outside of the city in another home but still, I thought this was weird. Especially since the first night he brought me home was not one of those out-of-town nights.  Call me old-fashioned but I don’t think it’s appropriate for a child to watch the lodger’s latest gay trick stumble through the living room on the way out, smelling of gin with his zipper undone.

Anyway, we had fun that night and the next morning I had a really unusual feeling, which was that I didn’t want to get out of there before he woke up. In fact we talked in the morning and I still found him cute and attractive. I wasn’t used to having been sober when first meeting someone who I later went home with. Normally my mornings after were spent being horrified at the not-even-cute-with-beer-goggles men I had decided to go home with.  Waking up next to someone cute and funny was a whole new world for me.

I wasn’t prepared for this feeling of still liking someone the next morning so of course I immediately turned into a nervous weirdo and when saying goodbye I asked if I would see him again in the most awkward way possible. This was the moment any upper hand I had ever held completely disappeared.

We went on a few more dates and I quickly revealed myself to be a needy, emotional, insecure wreck who drank too much.  What took me some time to realize was that The Rich Asshole was kind of a dick.  Our negative personality traits combined to turn me into an even bigger headcase than I normally was.  We had a few really fun dates but things didn’t seem to be going anywhere. He seemed really into me one minute and then the next he was cancelling plans at the last minute or being evasive about why he wasn’t free.  This was of course fuel to the fire of my crazy.

I got the sense that he was pulling away. Mainly because he had started ignoring my calls/texts. He eventually told me that the reason he hadn’t been in touch was that he started seeing someone else right around the time we started dating and it was getting serious. I got angry that he hadn’t just told me this but not because he was lying to me about why he was busy, cancelling plans, etc.  No, I was mad because I was so needy at the time that I would have been happy to date someone who was openly dating someone else.

A few days later I emailed him to say that I wasn’t mad and that we should be friends. Partly because we did have a lot of fun together and I thought we could be good friends. But also, the same delusional overconfidence that used to convince me that I could make straight men fall in love with me made me believe that he just needed more time to realize I was a better pick than this other guy.

We hung out as friends once and had a good time and I thought the groundwork I was laying for our future love was going well. But then, as anyone reading this who has half a brain would predict, he proceeded to string me along, make plans and then break them at the last minute, or, even worse, not bother to cancel at all and just not show up. He always had an excuse and a nutcase like me didn’t require much convincing. OK, I wan’t completely pathetic, I think there were maybe two or three times this happened before I’d had enough, but since I was convinced we were well on our way to being a happy couple it seemed like an eternity at the time.

Things ended as you might expect. He cancelled plans to go to an amusement park with me and a group of friends at 7am the morning we were going so I sent him an angry email informing him that he was a selfish asshole and that he was probably too much of a coward to reply.  His response: “I’ve upset you. Maybe this email should be it for us”.  His calm, rational response to my insanity made my head explode.

Thankfully he sent me what I’m guessing was a drunken email a few months later which gave me the opportunity to regain a modicum of dignity.

I was pretty bitter about the whole thing, especially the part where I behaved like an obsessive, insane person.  At first I put the blame squarely on him for being a selfish, manipulative asshole. And while I think he kinda was those things I think my reaction to his assholery said a lot more about myself and my inability to deal with rejection. And not to end on a faggy Sex and the City analysis, but when it seems like a guy isn’t that into you… he’s just not that into you.  I’m such a Miran… no, I can’t, I despise all of those women.

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