r: point taken- I was mainly trying to point out that “tricking women” is a strange way to look at it. If a woman doesn’t want to sleep with you you won’t be able to trick her into doing so unless there’s something really wrong with her, and in that case you shouldn’t want to. The game is mutually enjoyable if it’s played well by both sides, and when men act as if it were somehow unseemly or unethical I’m always tempted to wonder if they’re justifying the fact that they aren’t doing what they’d like to.
Unless you are downright phobic, the best way to deal with the fear part is to habituate yourself to it. A lot of experienced performers will tell you that stage fright never goes away- you just get used to it, and learn to function with it, and even channel it toward your own ends. You can start modestly- just start approaching women, having short, friendly, exchanges, and then going away. Very few women are going to react badly to that, as long as you don’t come off creepy. And a few might respond really well, and draw you out. Success breeds success. Just don’t put too much pressure on yourself to go out and get some immediately. At first, just having some pleasant interactions is enough.
Also, bear in mind that being a 47 year-old virgin is easier, in some respects, than being a 22 year-old virgin. Young women, particularly really attractive ones, can be really rough on men. They have a lot of men to choose from, and sex has more significant consequences for women than it does for men, particularly during the prime child-bearing years. The easiest way to winnow the field is to throw a lot of grief at the guys, and see who stands up to the treatment. Women in their mid-forties are, generally speaking, a lot more forgiving.
The other thing you can do is to start flirting a bit with women you interact with when you’re out and about- the girl at the coffee shop, or the woman at the post-office. Women love to flirt, as long as it’s clear that it’s consequence-free. I’m not talking about a crass remark, or a leer. Just send them a little twinkle and see what comes back.
One thing a lot of men do is act like they’re not interested in a girl when they are in fact trying to get closer to her- it’s like they think they can sneak it in real quick without her noticing… this is really transparent, and, at best, will permanently relegate you to “friend” land. So you need to get used to showing various levels of interest, but in a light-hearted way that says “I’m not going to stalk you.” Flirting a bit, even, or especially, when you have no intention of following it up in any way, will get you used to doing that. It will also get you free coffee 
.
I mean, I’m not saying that therapy or drugs might not help (beta-blockers spring to mind), but if you want to be having a different kind of interaction with women than you’re having, you’re going to have to change the way you interact with them on a fundamental level. And at some point that means taking the bull by the horns and making some changes- they can be very small ones at first.
