Danni, it looks like you and I are close to the same age, so I can understand your point of view. I'm not the dating type, so it was a big step for me when I asked a guy out for the first time. He paid for the meal too.
Although it's becoming more acceptable for women to take the initiative, the majority of women still don't have the guts to ask a man out. Hence, most men find it pleasantly surprising when they do get asked out, especially by shy quiet girls they totally don't expect that from. This already puts you in an advantageous position. I think if you detect that an available guy is attracted to you but he's not making any moves, initiative is good. Your chances of rejection are slim as long as you don't scare the guy off by stalking him, calling him every hour, or talking to all of his guy friends about him (thus giving them the impression that you are a stalker type).
Whatever you decide to do, good luck!