Yesterday, I met up with a classmate from my undergrad, Ras, who was in town on a business trip. I hadn’t seen Ras in 7 years. He knew me from years 18-21, which were not my best years emotionally.

He’s a tall, socially awkward guy who’s smart but also a tad on the angry side. I remember that at one point I had a crush on him, but not because I thought him particularly handsome or even appealing, but because I felt that he was the sort of guy I was worthy of, he was at my “level”. We were both awkward losers.  I thought maybe Ras could be the guy that I figured the “adult” thing out with, so that I could stop being a failure as a woman and my mother would stop asking me if I was a lesbian (not because she saw me with women, but because she never saw me with men). I remember, feeling giddy and excited when he would talk to me, even if the things he said were somewhat mean or extremely awkward because a boy is talking to me. The trouble is, I also remember distinctly that he rejected me. He said outright (well, typed via AIM, remember AIM?), “I don’t like you. I am not interested in you,” and implied that he would never be interested.  I was crushed, and at the same time completely unsurprised because of course what guy would be interested in me?

But that was at least ten years ago, and actually I feel that he was an awkward bullet that I dodged.  We’ve had a handful of exchanges over the years, exclusively via email or facebook.

So when he texted me, I figured why not?

The very first thing he said to me after saying hello and good to see you was, “You’re wearing makeup now.” And I made some joke about “putting my face on” so as not to scare the locals, but I instantly felt bad because either a) I’m wearing too much or b) he remembers that I looked terrible in undergrad. Awesome. Here’s a pro tip guys: Do not talk about a woman’s makeup. Simply say, “You look nice” or don’t comment at all.

And then the next thing he asked me was how many children do I have? He knows I don’t have any. He knows I’m not married. He knows I am a complete failure by society’s standards of women, so obviously this is his attempt at humor. I made some attempt at levity but then I said very plainly that children do not fit into my current lifestyle and he might as well have asked me how many private islands do I own. I actually had to repeat this again during our lunch when he kept harping on the fact that I don’t have kids or look like I’m in a position to have kids.

Over the course of lunch I discovered that he’s given up on art and has a “real job” at a bank. I said, “well, I have a real job too— at the bookstore, when I’m not freelancing.” And he says, “That’s not a real job.”

And I just swallowed it but it made me feel bad because it god damn is a real job.  I think about my coworkers and how would they feel if you told them that they don’t work real jobs? Retail has such a stigma in this country.

And then somehow over the course of the lunch, Ras decided that I was shy like he was and spend every night in like nun. He kept asking me “what else do you do?” like he wanted to know the exact number of times I go to bars or out with men.  And while I am introverted, I am not shy. I think those are two different things.  Lately, I’ve been isolated because I am so busy, but I do go out on occasion. I do not go to bars often. I am much more of a dinner and a movie or coffee and a chat kind of girl.  The last bar I was in, some guy used my shoulder as an armrest while he hit on my friends. So, yeah, I don’t like bars.

I was put in this awkward position of trying to defend myself and validate my choices.  I left our encounter feeling weird and a bit unsettled.

I keep thinking about why I felt this way. I think that Ras has an old-fashioned way of thinking, especially thinking about women. I am not much bothered by not having kids or being married. The only reason I ever feel bad about these things is because I am alone and being alone is hard, not because I am “failing at society”. I am non-conformist in this respect. I do not do things simply because I am told that I must, like a sheep in a herd.

I guess I’m bothered because I don’t know if Ras simply saw what he wanted to see in me (himself), or if what he saw is actually the truth.

I just left feeling bad about myself and maybe a bit embarrassed by the huge divide between myself and “normal” women.