I was in the dating game last K-con, and it was a lot of fun. I totally flubbed the first question though, but at least the other two guys up there did also. I mean, we all picked Major Motoko Kusanagi from Ghost in the Shell over Card Captor Sakura, but with all the potential reasons why, we just came up with wanting a more mature woman. We sucked. I was pleased with my other responses though, even if the randomness out of the hat kind of made things difficult. And I DID try to reply as my character would, which I feel all the contestants should.
Assuming the same rules as last year, I don't know how the initial bachelor/bachelorette is chosen, but the contestants are just picked out of the crowd, as Negima described earlier. Questions are pre-written, so the only improv is by the contestants. And while this is described as a dating game, no actual date happens, it's just for fun. I say this because some earlier posts made it sound like an actual matchmaking game. But seeing as I'm engaged, I'm happy the game is like this or I couldn't participate ^_^