Always wanted to be Inigo, when Willow said "Let's play Princess Bride." Not for the cool sword -- but so he could pretend he had a father who would have died to protect him. One he'd die to avenge. He always played Westley, though, because Willow asked him to, and there wasn't much else he could say but "As you wish" when it came to her.
(Jesse played Prince Humperdink, since *somebody* had to be the bad guy, and anyway how cool was it to actually get away with saying 'hump 'er, dink!' without getting yelled at?)
Read the book, would eat worms before admitting it, and would eat worms pickled in holy water before admitting that he used to play Westley for Dru. Though he did like the outfit.
(Edit: See, it has, like, narration and stuff. So I'm not really naked. I'm just wearing a really slutty low-cut top.)