Okay here's how the game goes you pick the most ugliest person you can think of and ask them out and date them for a month and make them cool then drop them and make them uncool. if you dump them before that month you LOOSE.
I feel like sasuke has the most potential out of the other guys
This is an interesting take. Normally a story like this is about a popular Sasuke trying to date then dump a nerdy [Name].