He's very shy and awkward so I don't think he'll make the first move. I'm not sure if I should because I have before and it didn't work out. We've been friends for almost two years and I don't want to ruin the friendship we have.
Also, my best friend doesn't like him. My best friends opinions come first to me. She used to be friends with his cousin but she turned out to be a snakey bitch. His ex-girlfriend a few years is not a nice person and my best friend has heard stories of what they used to do together. We both understand it's his past but to her it brings up concerns about the type of guy he is.
Most Helpful Guy
I'd make the first move and give him a chance. If it turns out he's not a nice person you can still break it off later, but at least then you know why you can't be together. And maybe if she gets to know him better your best friend will change her opinion too.
Most Helpful Girl
If you really like him, I say go for it. But since you said he's shy, I would slowly approach him. For example, try starting with small bodily contact. A hand on the shoulder, pat on the head, etc. But before this make sure you actually like him for who he is now, and not worry about what he might have been like in the past. One last thing: it's important to respect you're friends opinion but don't take it to heart. You opinion always should come first in matters like this.