Am I desperate?

I've been in and out of love three times in my 25 years. I've dated countless women in my life also and i've been single most of my life also.
The entire time the only woman friend (that i've never been with) that i have has been one of my best friends. I don't know why we never have hooked up. I've always been in love with somebody else or she has had a boyfriend. We're both the same age and most of our friends are getting married, divorced, having kids, or moving away. We've talked about how the pickins for getting mates is getting slimmer all the time.

Now for the first time we are both single and looking for somebody. It's wierd because I don't know if I should try to hook up romantically with her? we get along great, and I also think she is very attractive. The problem is that i think that we are both very vulnerable right now. We are both getting over serious relationships. If we hook up would it be because we are both desperate? or could it be that there is a chance it could lead to something more. aghh! what should I do? I really want to try, but it's the classic tale of "what if it doesn't work out?"

Would you guys take the chance?