Does he or doesn't he

It's funny how when you stop looking for a relationship there are suddenly a ton of opportunities. I'm currently flirting with the possibility of dating Jacob. Everyone says that he only comes over to talk to me and blah blah blah. So I'm giving in and trying to get a feel for the situation. He is a great guy, and he has done some really nice stuff for me and my friends over the past three years or so. It feels like he's a part of the group, and I like that. The problem is that he is so shy. It's kinda hard to get to know him, and it's so hard to sense the tone through his text messages. So I don't know if everyone saying he likes me is just what they think, or if he actually does. If he does, then things are moving really slow. Not that there's anything wrong with that, but I'm impatient. And now I've got all the thoughts in my head because I'm a girl and over think things WAY too much. Dating is just so awkward. How do just go up to some one and say "I like you. Wanna go out sometime?" It's so much easier said than done. And I wouldn't want to turn the games into an awkward situation for everyone, not just him and I. I just can't be the one to go out on a limb like that. I have been hurt way too many times, and maybe he has too. I just wish I had a better feel for things, and that he wasn't so shy sometimes. But either way, it's nice to have a decent guy to focus on for once. :]