How do I get him to be unscared? (Advice for a confused teen.)?

Here's the thing. I've known this guy for about 4 years. We like each other a lot and openly say we love each other all the time. I asked him why he doesn't just ask me out already. His response was that he doesn't want to take the gamble because I make him feel something he doesn't really know how to feel...happiness. He's basically scared that something bad will happen if we go out. However, I'm not going to waller in self pity and wait around for him, if he doesn't ask me out & another guy I like asks me out, I'll say yes. Yea, I don't want to lose my best friend of 4 years, but he doesn't want the gamble of a relationship, but doesn't want to see me with anyone else. To be honest, I'd hate to see him with anybody else either, but I'm basically the only girl in his life besides his mother and sisters. We love each other, but he hates having feelings cuz "they drive him crazy". Apparently, I came around and turned his perfect little figured out world upside down. He wants to spend all his time with me, but I am gonna flirt and I am gonna go out with other guys if he doesn't. I talked to a friend and she said just to wait, but the thing is, a) im not patient and b) i waited for at least 2 years. We have liked each other in that way for 2 friggin years, we know everything about each other, and he's scared. How do I gt him to be unscared, maybe not even for me, but in general, he's scared of forming bonds of any kind, I don't blame him, but he's so unhappy, I hate to see him unhappy. I don't care if we really end up together or not I just want to convince that not every person is gonna trash his heart. And that he can't live his life all alone and be happy.