Loser No More
I am a 24-year-old guy who has never had sex. I haven't even had a girlfriend since I was 15 years old. When I was a teenager, I was a basket-case punk rock kid and I never really let anybody get close to me. Basically, anytime a girl was interested in me, I was afraid and pulled the whole fifth-grade "make fun of her and blow her off" thing. This had a lot to do with my being mixed up and wasted all the time, but it also had a lot to do with my being a giant pussy about the opposite sex.
Now that I'm older and fairly well cleaned up (at least as cleaned up as I'd ever want to be), I find myself stuck in the mindset I created for myself years ago. Whenever it might seem like a girl wants anything to do with me, I kind of flirt around with her, never having the balls to make a move toward anything, and eventually end up with a friend.
When I was growing up I was a 300-pound lardass, and because of it very few girls were ever into me-which kind of explains my fear of them (after all, I didn't want to reveal the oceanic folds of flesh hidden by my extra-large Black Flag shirts). Nowadays I'm in much better shape, have a good job, etc., but for some reason I still think of dating and relationships as being similar to jumping off a cliff.
No matter what, I can't convince myself to really go for it, because in my heart I just know that any girl's interest in me has to be an illusion. I keep thinking this is just a big case of my being a big wimp, and that I just need to jump in and get beat up and get used to it-and get over it. I was hoping you might have a little bit more advice for me.
-Complete Sexual Retard
You are a former fatty. While definitely more socially acceptable than being a present-day porker, there are a whole host of problems that come with dumping a ton of weight. The worst of all being that while your body has slimmed down, your brain still hasn't accepted this fact. I'm not talking body dysmorphia (the phenom that causes you to look in the mirror and see a chubster), I mean that you still feel as crappy about yourself now as you did back then. You are not that fat kid in the Black Flag t-shirt anymore, so quit it.
The first thing to realize is that you are not unique. There is nothing terribly weird or unusual about what you are feeling. Please appreciate that there's something very freeing about knowing there are approximately a bazillion other people out there who feel just as socially retarded, unattractive and losered-out as you do. True, Paris Hilton probably never struggled with feelings of unworthiness, but then I'm guessing she doesn't have a lot of time for introspection. Most of the rest of us have felt just as bad or worse at one time or another. And many of these same basket cases are getting laid in spite of themselves.
You're not off base equating dating with jumping off a cliff. There are risks involved with both, but even on the most horrific date, one can usually manage to hobble home with all limbs and organs intact. The worst thing you could possibly suffer on a bad date is rejection. Which is painful, but who hasn't been shown the curb? Been laughed at? Publicly humiliated? Big deal. Being made a fool of builds character. Hell, I've been rejected so many times I gave up counting once I hit 300 (about a decade ago). So some perky-boobed bim isn't interested? Next! Perhaps her naughty-librarian-lookalike neighbor will be.
Whatever you do, don't make any more female friends-at least until after you get laid. You need to concentrate, and lame crushes will only distract you from your mission. This is why I suggest giving internet dating a try-this way it's obvious from jump that you are both potentially interested in seeing the other naked. Nobody goes online to make friends, so there's none of that ambivalent crap you have to deal with when you dick around getting to know someone first.
But you're not going to be able to see some cutie's boobies if your face is busy scouring your own colon. So pull your head outta your ass and buck up. Quit being a big girl's blouse! Look around you-people far uglier than you are having sex! Talk to girls, go online and get out there. And if you find yourself lapsing back into old behavior and wanting to put gum in your date's hair, retreat to the bathroom and bang your head against the urinal until the urge passes.