grap3fruitman said:
I'm a little confused. Could you clarify? I'm supposed to do well with women by going out and practicing doing well with women?
I disagree and I think this is a horrible analogy. Riding a bike is nothing like talking to a person. Riding a bike is such a simple concept, dealing with people is so horribly complicated because people are complicated. Let's go back to your analogy for sec: if you kept falling off your bike and never managed to ride it once, what would you do?
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But regarding that analogy: if that batter has never hit a ball, he's probably fucked, right? What's he supposed to do?
Few things to pick up on here. First, to address the batting analogy and your first point here: practice makes perfect. In your case, that does not mean practising doing well with women, it means practising doing something, anything, with people generally. You've said you're uncomfortable with asking for directions and the time, so start taking yourself out of your comfort zone by asking these things on a regular basis. A previous poster gave some good advice earlier about asking for help at the book store. This can work with any hobbies or interests you have. Games are an obvious example, although employees in game retail are unlikely to be the best for social interaction

Another (real life) example: since I'm interested in music, the other day at a music shop I asked the girl at the counter for help with something and ended up in a conversation with her. The conversation went on for over an hour until the shop closed, and then we went for a drink to continue talking. I wasn't expecting anything out of it, I didn't even get her number or facebook. It's best a lot of the time to take things as they come, especially since for now you should want to concentrate on bettering your general social skills rather than going after a girlfriend.
How does a batter succeed? He has balls constantly thrown at him until he finally does connect with the bat. And when he does it once, he keeps going until he does it again, and again, until it becomes easy. To extend the analogy further, it sounds to me like your issues with handling those four women who expressed an interest in you, were to do with the ball being thrown too fast, so to speak. You were going from the safe, slow-ball environment of work, surrounded by familiar people and social situations, straight to the challenge of pro league. All of your missteps are completely understandable when you look at them this way - you were a rookie thrown to the lions. The trick is to build up your social interactions with a more gradual curve. I hope what I've written in the previous paragraph will give you some ideas as to how to achieve this - a few other posters have given useful advice on this front too.
Finally, the bike analogy. I think you've written it off when it actually illustrates an important point. You're right to note that people are complicated, hence social interaction is in one sense dissimilar to riding a bike. But the concept of riding a bike is useful since the responsibility of success falls on the rider, as the person in control. People may be complex and outside of your direct control but your interactions with people can be brought under your control with practice, just as the cyclist brings the bike under his or her control, with practice. People are really remarkably socially adept and fluid. In a two person conversation, when one person asks a question, the other gives a relevant answer. What I'm trying to get at is that conversation does involve a large degree of control and predictability, otherwise our conversations would be nonsensical. Because of this, the skills you pick up from one conversation are transferable to another. A confident conversationalist will drive the discussion, and seek out subjects of mutual interest.
I hope this will explain why I recommend social interaction with anyone, any age, male or female, attractive or not. There was a poster earlier who mentioned how their job enabled them to make small talk with anyone, including making them laugh. I can tell you now that if a girl is going to want to enter into a relationship with you, good conversation skills and the ability to make her laugh are extremely important, as well as the self-confidence which should develop naturally amidst self-improvement.
Now I really hope that you'll give this advice some thought and not ignore or dismiss it out of hand. You're by no means fucked or a hopeless case as long as don't do that with the advice people have given you here.