It's presented as a joke, but he seems to put the opposite sex on a pedestal above himself. It's easy to see that as a self-esteem problem.

"You know your self esteem isn't high when you're not so much threatened by the competition as by your date herself."

I don't think he'd be threatened by dates if he saw himself as equally (or more) worthy than the date is. He is entering into it with the assumption of having to justify himself to this person. In other words, his base assumption is that they are better, and he must prove himself. This is self-defeating, and all too common with western-men today.

"convince a woman I'd never met before that I wasn't a deranged serial killer was going to take all of my Jedi powers"

You don't need to convince a woman of anything, this isn't a used car sale.