New Year's Eve date

I am starting this blogging process by going through all my old emails, many of which were the result of internet dating posts, and trying to make a funny story of them before finally sending them to the recycle bin. The first compilation is from two December's ago, and this is how I remember it:


So after the Christmas holidays the lack of having someone starts to get me down. I know that I would rather have someone in my life to exchange silly presents with; someone to walk through the streets of New York with, enjoying the silence that can only be achieved by blankets of snow. Since I don’t have that one person to snuggle and drink hot chocolate with, I turn to my trusty friend – the internet – to find me a man.

Placing an ad entitled “Santa didn’t bring me the Man I wanted” I begin the process of weeding though the losers who didn’t go home to their own families for the holidays and are, like me, stuck in the city with no one during the coldest part of the year and are looking to meet someone knew and kindle a fire all their own.

In my ad, I suggest meeting for ice cream as a first date. I would normally suggest meeting for a drink, but I don’t drink alcohol and while I am fine with my personal choices I don’t want to have to explain them all to someone I may or may not have an interest in. There is nothing that kills a prospective connection like saying “Oh, I don’t drink, but don’t have a problem with people who do. It is not a preachy thing, I just don’t like the taste. Yes, I have dated a bunch of alcoholics, and I grew up with an alcoholic parent, but it isn’t about that – really, I just like Pepsi instead.” Not exactly the kind of conversation that makes a guy want to meet up. I also think that because I don’t drink guys think that I will be a stick in the mud (or they know that there is no chance of getting laid by getting me sloshed) so don’t want to meet. I digress – so I suggest ice cream instead.

If one were to live in another city, dinner might be a good suggestion. My best friend in NC has internet dates all the time that involve a sit down meal, but New Yorkers aren’t ready to make that kind of commitment – financial or otherwise. So ice cream it is.

And I did have a good response from a guy named A.B.:

I love ice cream. I also like coffee, but that is more out of need at this point. Like you my Christmas wasn't perfect but it wasn't bad.

So I live by myself. I am 33 and gainfully employed. I am a lawyer working in financial services (I don't love the job, but I very much do like and respect the people I work with). I secretly believe that Love Actually is one of the best movies ever made. Sports are always good. I don't smoke or do drugs - nada.

I think I have a very good sense of humor - especially about myself and particularly when things don't go to plan. Which also means I am laughing quite a bit. I also try not to take myself too seriously.

So a little more about me: I am 33 SWM 5'8", really enjoy traveling. I like to go out, but I also like to stay in. I bet you the cost of ice cream/coffee (your choice) when we meet you can guess what part of the city I live in.

So the ball, puck etc is in your court. It would be great to get an email back from you. I can be IM'd at uwsguy on AIM or Yahoo.

Now, the betting is a cute idea, but it also makes him seem like he would have made me go dutch on the cost of an ice cream cone if I couldn’t figure out from his IM address that he lived on the
Upper West Side. He wasn’t expecting a genius, was he?




We agree to meet up – and on my side of the park no less, because he is having a piece of art stretched. That was one I had never heard before.

Nice guy, simple enough. We had Cold Stone Creamery and walked around the neighborhood. Though he was classic WASPy lawyer, he seemed nice and I was willing to overlook the obvious blue button down shirt, khaki pants type of guy he was. The date lasted maybe an hour and as we parted we had the sort of hug, almost kiss on the cheek moment. And the next morning I got this email:


Had a great time last night – I hope that you did as well. We should get together again. :)

Let me know what you might be willing to consider for New Years.

How was I supposed to take that? Nevermind the fact that an adult man had used an emoticon in an email to a girl, I was willing to overlook it because I wasn't sure it was a usual thing. Beyond that, I had spent approximately an hour in the company of this man and he was asking about New Year’s Eve? During the date he had mentioned that some people at his law firm where having parties and he was trying to figure out where to go. While I didn’t have solid plans, and actually was pleased at the potential invitation to one of his party options (all the better to wear my new fancy cocktail dress), I was curious about the “willing to consider” part. So I asked him about it and he replied:

LOL, listen I am not trying to be the creepy Craig's List guy. I just wasn't sure if you would be comfortable coming over watching a movie, watching the ball drop and staying over. And I am not suggesting there would be sex. It just would be nice to wake up next to someone. That's all. Nothing weird.

I know that he said that it was “nothing weird” but how weird is it to have a second date at his house, with the accepted notion that I would be spending the night? No thanks. I don’t have any prejudices about sleeping with someone too early – if you want to knock boots on your first date even, I don’t judge (I may have even done so myself) but to set it up as part of the plan seemed forced and presumptuous to me. I had to wonder if the only reason he was cruising around the classifieds was to find someone for the upcoming holiday.

So I declined the invitation and spent another New Year’s alone.

I guess it is a valuable lesson to realize that my own company was preferable to being with someone who just wanted a warm body to fill the empty space in his bed, even on one of the highest pressure “must be in a couple” nights of the year.