I stumbled across this fun — and beautifully designed — site today. Type Connection is a game where you play matchmaker and pair typefaces in a way that is reminiscent of dating websites.
The site is actually the MFA thesis project of design Aura Seltzer. Combining type history and nomenclature, the idea is for the user to develop a better understanding of pairing typefaces while playing.
After selecting the two typefaces you want to pair, you get to see how they match up before sending them on a date.