Type Connection
One of my fellow designers sent me this one. Very cute way to learn a little about typefaces and how to pair them. A Typographic Dating Game — you get to send them on dates! See if the X heights are similar, or the terminals, or the stems :) wooooo nerdy! love it! Go play here!
stream of consciousness 
Fun! But I tried to fail since I wanted to see how they would explain why a pair DIDN’T work, and it just kept succeeding… I think they only let you make pairings that work!
if you fail, it gives you an oops popup.