RaunchIsGoood said:
I really wish I could think of it as 'I got nothing to lose' when I asked a woman out, but it just doesn't seem to ever work that way. Even though I'd like to, I don't have the guts to consistently hit on random girls at bars or anywhere for that matter. I've read some stuff with regards to how to pick up women, but I don't think I'm brave enough to actually give it a try though as this shyness is pretty extreme for me. While not a stud, I don't think I'm unattractive at all and had it not been for being shy, I'd probably had done well with the ladies.
I don't visit SPs or MPs, and I'm saying book a well-reviewed SP.
I'm going to go Dr. Phil on you... (With the obvious caveats.) At this point your virginity is probably undermining your ability to pick up or have relationships...
I'm an average guy, with average income, a little bit your Jr. I do Strip Club Safaris only, and not generally for sex. (Periodic gratis handshakes aside.) The vast bulk of sex I'v ever had has come from hooking up, or withing the context of a relationship. IMHO, I do 'well enough.' I'm not shy, but I'm awful in any forced dating situations. Be it a fix up, or dating site, or whatever. I'm also not a club guy, or a really smooth player.
Here's what I figured out:
-Go out with friends to places that have people of both sexes and where you're comfortable. Maybe apply some booze, or herbs and spices, to the 'relax' point, but not the 'wasted' point. Have fun and have zero expectations.
-Should you bump into a woman while having fun... You know that one you trampled on the way to the washroom, beside you on the patio, or next to you at the bar. Yeah, that one. Forget sex, forget relationship, forget imagining her naked. DON'T forget she's a woman (or just avoid the worst male'isms'). Make some smalltalk-- be interested, interesting, friendly, and as honest as you can get away with. It's OK to be a nice guy, and it's OK to be shy... But you gotta get those lips to move. Remember, zero expectations, be sincere, and not just to people you're attracted to. Heck, I'll chat with guys pretty much the same way (with the male'isms'), and even that girl who really wasn't your cup of tea might have a friend (and feel the same about you.).
-Odds are at some point you'll have to go back to your respective peers. If you're lucky at this point you might get a number or an offer to go someplace else. Probably not. If you're getting a really good vibe give her a way of contacting you or ask her for her info. In most cases a chat is a chat and don't try to be passing out business cards to everybody you say 'hi' to. Don't be a lame ass, don't make a great display of buying her and her friends a pile of drinks, don't stare like a puppy, and don't stalk her around the place. Not cool. JUST KEEP HAVING FUN.
-Force yourself to keep chatting with anybody you bump into. Don't be intrusive and take a hint. But always remember you just having fun. Now, with that being said: be aware. Is somebody you bumped into sneaking peeks you you? Is she going out of her way to walk by you? To bump into you again? ARE YOU INTERESTED? If so... Does somebody interest you and nothing's happening? All you can do is 'arrange an approach' and learn to take a hint.
Everybody I've hooked up with, dated, or been in a relationship with has come about via this process. No expectations, no games, no real 'system'. Not any real trying. Heck, I even got my previous job that way.
Your shyness is probably 'the problem' but if you're fixated with your virginity, losing it, and your lack of experience while losing it, that will 'show' to any woman you're talking to. Your virginity is something you can 'fix' in short order, you're shyness is something you must work on. I'd suggest doing both, see that SP but make sure you 'force yourself' into new social situations as well.
I would suggest, that if you start seeing SPs you also force yourself to get out in social situations and participate there as well. SPs, even GFEs aren't real 'pick ups' and aren't real dates, and aren't real love... And everybody should experience that sort of suffering a few times first hand

A healthy hobby is one that fills a nich that is of value to you, not one that dominates your life. My fixation with SCs is about the 'safari' quality of going to strange places for beer and boobies. I get a modest thrill of danger and fun 'in the hunt'-- It puts a smile on my face for weeks to come, and best of all it's helped condition me to keep my cool when beer and boobies happen in my normal life. So play safe and have fun and get out there!