1. Find out his favorite band, tv show, movie, or comedy troupe (this should be easy, if you aren't discreetly listening to his conversations you don't really like him).2. Familiarize yourself with these things. Watch the movies and tv shows on Netflix or Hulu, or rent them, listen to the band on YouTube, or whatever.3. Begin to wear shirts depicting these bands, shows, movies, troupes, etc.4. He will inevitably comment on your shirt. Say thank you. The next bit is up to you. Guys go crazy when the girl initiates.