I am a 32 year old computer programmer. My problem is simple: I have never had a girlfriend. To be truthful, I don't even know where to begin.
For the majority of my life, I've had my head in the books. (I graduated from Stanford). When I started working, I had hopes of meeting someone compatible, only to find that there are no women in my field. I see cute women in the office cafeteria, so I know they exist around here, but I spend the majority of my time with my colleagues in my department. To be honest, none of us seem to have much of a clue.
My siblings suggest I go to bars and clubs, but I have never been very good with small talk. I tried okcupid.com one time, but I'm not the best-looking guy, and the results just proved depressing. I know I could make the right woman very happy.
Forever single in Forest Hills
Dear Forever Single,
This letter broke my heart. I feel like I need a magic wand to help you out. The kind Cinderella's godmother used to make her over and get her to the ball. 32 years old and never had a girlfriend?! That is rough.
I'm glad you have the good sense to avoid internet dating sites. I'm not trying to be mean, but those sites are not designed for anyone physically-challenged in the looks department. Something about anonymously swiping through hundreds of profiles a day brings out the shallowness in a lot of people. Bars and clubs are also not a good place for you to pick up. Something tells me you are not only "not the best-looking guy," but you are also socially awkward around women. It's the fact that you choose to hang around your clueless single male colleagues instead of talking to the cute women you see in your office cafeteria. That and the fact that you probably make a fairly good income as a computer programmer and still no woman has dated you.
Listen, I can't be your fairy godmother, but there is some woman at your job that can be! No one gives a man better advice on dating than a woman. A woman can advise you on your appearance, where to meet single women and proper dating etiquette. Your mission, should you choose to accept it, is to find a woman at your job who will help you out and guide you.
Step one is to find the proper woman at your job. She doesn't have to be the best looking, just the least crazy looking. You know, someone who looks like she actually goes on dates. So avoid the woman with bifocals thick enough to stop a bullet. (And if it's you wearing the bifocals, get some damn contact lenses.)
Step two is to establish a friendship with this woman. Since you spend 8 hours a day, 5 days a week in the same building as this woman it's not going to appear weird if you start acting friendly. Okay, it might, but at least it's a captive audience and she's more likely to be polite to the weird co-worker than the weird guy on the subway. Start with hello and then work your way up to casual conversation. Ask her how she likes the job, what she does there, where she is from, where did she go to school, etc. Keep the focus on her. Do not, I repeat, DO NOT blurt out I'm 32 years old and ain't never had a woman. One, she may think you are a serial killer that has selected her for your next victim (especially if you are a crazy looking white man. Sorry, but statistically you do most of the serial killing). And two, you have not established a rapport yet, so she has NO interest in helping you at this early stage. So wait a while before you spill your guts.
After a good two or three months, after you feel like you two are cool, then ASK her if she's willing to provide dating advice. Ask her about what you can do to fix your appearance. Where are the good spots for meeting single women (she might even hook you up with a friend) and once you score a date, where you should go. After you've had a date, go back to her and talk about it. If you are good enough friends at this point, she'll tell you what moves you made that were good and which moves you made that sucked.
Step three, once you have a fairy godmother at work, is to focus on places where you can interact with the same women on a regular basis, giving the women a chance to get to know you personally. I would suggest work, but since you are in one of the fields with the fewest amount of women, the competition may be fierce there. Try book clubs or dance classes (even if you can't dance...which I know you can't). There are so few straight men in these settings, the women will be more likely to speak to you, especially if they see you on a regular basis. I hope this advice has been helpful, Forever Single. Good luck, and may the Force be with you.