Most Helpful Guy
I just think you put too much pressure on the actual "date" part of it. I would down grade the meeting to just simple coffee or a walk in the park. I would also spend as much time just generally talking to the guy to increase your comfort level as much as possible before you do meet up.
Most Helpful Girl
Almost everyone feels that way, it's normal. If you keep dating more people, it will stop being such a stressful activity.