Monday, January 03, 2005

NYE Boys

I got dolled up for New Year's Eve. Why? Because I love to dress up for fun events, even if I prefer to be a slob on an everyday basis. After CM I rode home and threw on a little black dress, heels and lipstick (OK, my dolling up isn't all that extensive and still takes less than 5 minutes). Then I got the super-great fun of biking in the heels and dress to the party in DECEMBER. Fantastic. I also learned an important lesson about my little black dresses--one is fine to bike in, but this one is completely scandalous, even by my biking/flashing standards. Thankfully it was dark and I was wearing underpants.

After several minutes at the party I realized that something was weird--I was one of two women at the party and the other had a newborn and husband in tow. Fortunately more women showed up throughout the night, but the ratio still skewed overwhelmingly male, and most of the women were 'girlfriends'. Additionally, the word recently got out that I am now single. The intersection of sausage party, my 'fresh meat' status and the lipstick/dress combo created a different dynamic between me and some of my bikey guy friends. This only became worse as the evening continued and the alcohol ran freely.

Yuck--there are few things that make me as uncomfortable as men who I am not interested in expressing interest in me. It's bad enough when these men are just strangers who can be brushed off rudely if necessary. It is entirely different when the guys are men who you know and want to remain friends with--or at least know you will have future contact with or share social groups. I don't know how to gracefully stop them from embarrassing themselves. This is probably partly my awkward ineptness and partly the inability of many men to be able to read women's signals adequately. So anyway there were a several uncomfortable moments and several guys who I don't look forward to seeing anytime soon.

But, beyond this I still managed to follow my New Year's Eve tradition of developing a connection with a cool boy from a different city. This year's state: New York. Also following the tradition--he's the younger brother of a man I hope to develop a professional/business relationship. Breaking the tradition, I did't make out with him in front of the older brother and other family members. He is Todd's brother who I met the night before at Alex's party. We had some chemistry on Thursday, but only spoke for a bit. Friday night things seemed more interesting, but we were both mingling a lot at the party--a few times I sort of used him as my 'shield' to deflect unwanted boy attention, but nothing too overt. He and I then biked over to a party at the lower apartment of Todd's place and hung out there together for quite a while.

This party was sort of the same thing--except half of the guys were gay. Doesn't matter. For some inexplicable reason stereotypically gay guys who are overly concerned about appearance and fashion just adore me. This is completely perplexing because even a cursory inspection of me reveals way too many 'mistakes'.
  • Shoes--Payless, circa two years ago;
  • Legs--unwaxed;
  • feet/hands--unmani/pedicured;
  • hair--boring cut/no product;
  • dress--again, two years old and not 'stylish';
  • handbag--bike panier;
  • make-up--just lipstick;
  • body--chubbyish and flat-chested.

Even when I am not 'dolled-up' this type of gay guy just loves me. It is truly a mystery of my life. But anyway, I digress......

So the boy and I spent a lot of time talking as other men drifted in and out of the group. Eventually Todd and some other bikey people arrived. One of them was totally trashed and started to insist how cute of a couple we were and that 'he had a feeling about us' and 'if you aren't at that level yet, you soon will be'. Ummm yeah--too bad he was too drunk to feel the awkward silence that built from his 'compliments'. When the party wound down the boy, Todd and I all went upstairs to talk for a while. What makes more sense than extending the evening until 7:30 in the morning? Obviously, nothing happened under Big Brother's eye and I biked home and napped straight through polar bearing.

Todd and I talked later and decided no Lake Michigan for us--too late, too lonely, too cold. An hour or so later the boy called to confirm the bailing from the already bailed plan and to tell me that he was leaving for New York that night or early Sunday. I wished him a nice life and he said that we'd see each other in the future because he visits Chicago regularly. Cool.

The next day he called to say that he was postponing his trip and that he happened to have an extra ticket to a play that evening and would I join him, Todd and Lisa? Well, yes of course. It was fun and nice--plus it is always reassuring to have additional confirmation that my read on people is accurate. It is nice to just get confirmation that there are indeed cool, wonderful, smart men with whom I can share a mutual attraction. If we lived in the same city I think we would probably have a blast, but we don't so the flirt should just be enjoyed for the moment.


So for three years in a row I have met a fun new boy on NYE who was perfect for the moment. Maybe my NY resolution should always be to begin each year flirting with a cute, smart boy without the worry of what it will lead to. However, I do have some regrets:

  • Not going out with Todd to meet his out-of-town brother on Tuesday night--I could have had a week of flirting instead of a weekend. Dammit.
  • Not being more affectionate with the boy in front of the other guy bikey friends--this could have killed two birds by making the guys think I was attached and by just racheting up the flirt for fun's sake.

Oh well.......this also helps me to put the adorable lawyer boy in perspective.





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