Regrets, I've had a few....

A few days ago, I was talking to a student worker who was essentially complaining that people trying to be social were distracting him from his work and from school. I commented that he should probably try to strike a balance and allow at least some time for a social life, or he might regret it when it's too late... like me.

Of course, I was projecting - and if I'd spent a little more time in college focused on having a long term plan, like grad school or law school, instead of a short-term plan of figuring out how I could smuggle two 30-packs of Shaffer Light into my dorm, I might be in better shape today, instead of in a somewhat dead-end job.

At the same time, I think when I graduated and started my job, I started focusing on two things that were (somewhat) important, but that I allowed to replace having any sort of a social life, which has contributed to my current lonely, single existence.

Those two things were buying a house and getting my MBA. I wanted to make as much money as possible as quickly as possible so I could put down a down payment, so I jumped at the opportunity to work overtime pretty much every Saturday - something I did for nearly three years. Working for a college gets you certain perks, including free tuition, so I started taking classes at night. While neither thing was that significant, the combination of the two took up pretty much all my free time. It took the place of having a social life, so I didn't really notice that I was alone - that I didn't really go out, or date, or talk to people outside of work or school.

And then I bought my house, and at the same time my overtime went away thanks to some restructuring. And about 8 months later I finished my MBA. So now I have a ton of free time on my hands- no classes eating up my weeknights, no 8-hour shifts on Saturdays eating up my weekends, no financial statements or reading that I have to get done in the time in-between. And when I picked my head out of my books and my checkbook, I noticed that I didn't have a whole lot of friends. That I was single, while most of my coworkers, classmates, and people my age were married.

I can't help but wonder if I'd had more free time as a 23 year old, if I would have noticed that I was lonely and made some positive changes before it was too late, before I became a bitter, single 27 year old. I feel like it's too late for me to start a relationship, that all the decent single women my age are already married off and popping out kids. I've tried dating sites, and most of the single women seem to fall into one of a couple categories 1) they are single because they have massive baggage (divorce, kids, bad relationships) 2) they are single because they are horribly ugly or nuts (including one whose profile included "have you ever wanted to kill yourself but are too lazy so you decided to try online dating?" or 3) they are single because they don't really need a relationship - they have a bunch of hobbies and/or are attractive enough that they can afford to be picky (ie they are out of my leauge) or 4) they aren't really interested in a long term relationship or settling down.

I feel like every day that I'm single, my chances of meeting someone go down as more and more women my age enter relationships and get married. When I've talked to other people about online dating, they've accused me of being too picky, of not contacting women because something small seems like it wouldn't work out. But I feel that I can't afford to waste time on a relationship that is unlikely to turn into anything. Of course, there is probably a healthy dose of fear of rejection and low self esteem mixed into Mad Anthony's dating theory slurry.

And there's one other regret - one other answer to the what would MadAnthony do differently if he could go back in time. That something is losing weight. I've dropped a few pounds in the last couple years, and a few inches around the waist. I probably could still stand to lose a few more, and I probably won't, but I no longer have to special-order size 46 pants from OldNavy.com. Being fat has always hurt my self-esteem, and probably hurt my chances with the ladies. Losing weight earlier in life probably would have helped me be more attractive and more confident.

Or maybe not. I don't feel any more confident - if anything, I think I grow less and less confident each day, as I feel my chances of ever having a real relationship grow smaller and smaller. Losing weight has made me wonder something more frightening than the thought that women didn't like me because I was fat - that maybe women don't like for another reason, like because I'm an asshole. Because I come off as not liking anyone until I get to know them. Because I'm not very interesting, because I don't have any cool hobbies or an interesting job or an ability to talk to people without staring at my shoes (although I have been told I have good taste in shoes). Those are things that are far harder to change dropping a few pounds.

When I commented to the student about my regrets, another coworker commented that I was single because I have a defeatist attitude. I don't think that's totally true - when it's things I feel like I can change, I do OK - losing weight, saving money, getting a decent score on the GMAT, getting my MBA. But when it's things that require external factors I can't control, it's harder. Dating is one of those things. While I can make some positive changes - try to improve my apperance, try to be more interesting, try to put myself in social situations or on dating sites - I can't make women like me, and the longer I go being single, the more I feel that things are out of my control, and the more defeated I become - which makes me want to do less, and thus starts a vicious cycle.

And makes me wonder if things would be better if I'd made a few different decisions a few years ago.