NYC You and Raise

I'm in NYC again for work. This time, though, I finally was able to
meet up with a friend for dinner. My friend from UVA is here. When we
were in college, we spent many hours throwing each other around. We
met in karate class, would spar with each other, then we'd race around
the city getting slurpees or going to the driving range. He is a
really smart, funny, generous guy who happens to be a trader and
living in NY these days.

He is also a relationship guy. Essentially the entire time I've known
him -- not quite 10 years -- he has had a serious girlfriend.
Unfortunately, he recently broke up with his girlfriend because they
realized it just wasn't going to work. And, those breakups are the
hardest. Its much easier (long term) to have a breakup where someone
does something awful and then you hate each other. Just not being
quite right sucks because you still like each other. Sucks even more
when you are still living together because NY apartments can take
awhile to find.

So he picked me up in his "city car" and off we went to dinner at
Colicchio's craftbar. (Note: the "city car" is a porsche, the "country
car" is a Ferrari that apparently bottoms out just trying to get out
of the city. Traders.) Whenever I see him, its just like UVA level of
friendship even though we are really bad at staying in touch and only
see each other infrequently. For example, he and his girlfriend stayed
with me in Chicago for about a month some years ago while he worked
out a job situation. The next time he was in town -- a year and a half
or so later -- he showed up with a different serious girlfriend. Bad
friending by me and him but whatever. We had a good discussion,
including our current problems. He saw my job problems, and raised me
relationship problems. And, I fold -- especially as he, being a
self-made, self-directed guy offered me an idea of how to go out on my
own and side-step firm life. Unlike his trader-self, I'm risk-adverse
but its something I will at least consider.

Anyway, we had a great time and it was so good to see him. Plus, it
made me appreciate even more just how hard it is to be single,
especially if you're not as lucky as I think I am to have some really
good and reliable friends. Got to witness the difficulty of his
position when his ex-girlfriend joined us later for dessert and drink
after what she described as discouraging apartment-hunting.