Waiting, Doubting

I have learned the lessons of He's Just Not That Into You, and I understand that if a guy really likes you, he'll make the effort to find you and ask you out. Even though I'm well-versed in this area, I've always found it tough to sit around waiting for a guy to make a move, and especially to trust that a guy will make a move. I guess I don't give them, or myself, enough credit, but I often feel like nothing will come of a first encounter unless I take charge of the situation.
Many women believe that taking things into their own hands is the right way to approach dating. Unfortunately, being the first to call or message a guy means you are putting yourself out there, and then leaving the ball in their court. Once that first message is left hanging in the air between you, there's not much else you can do without seeming a desperate stalker. Although I convince myself it's best to be proactive in dating, I end up being much more doubtful of myself after getting no return message. I would have been better off risking my chances and waiting for them to reach out. At least then I could have convinced myself that I was impossible to track down.