I'm not into the whole bombing the trail thing, so I've been spending a lot of my time in the park. Yeah, it's easy to psych yourself out either before you drop to hit a feature or while your approaching a feature. Just start as small as you can and gradually work your way up. Don't feel pressured to try something you feel very uneasy about because of your friends. Also what helps me a lot is learning to control yourself when you fall. When I slip off the heel side of the rail, I always try to use my hands to feel where the rail is on the way down. If I start a grind and I know I'm not going to ride the whole rail, I don't fight the board and try to keep it on the rail (well, I did try to fight it once, and I split my shin open on the rail). Hopefully that didn't just spook you some more, but that was only because I was getting greedy on a down/flat/down rail that I should have just hopped off when I felt iffy about the approach.
If you keep trying and trying and things just don't get better, then perhaps freestyle just isn't for you, the same way bombing blacks and riding through trees isn't for me. I feel like i'll never get comfortable straight-lining a black, so I've happy accepted my place in the park