Type Connection is a game that teaches you how to pair certain types of fonts together based on certain characteristics, and you learn by sending two different typefaces on dates. First you pick a font, then a date strategy and finally a partner. If it works out you'll learn why your choices were good. If you fail, you'll be told why and sent back to try again.
You start with a few choices between popular serif and sans-serif fonts -- a distinct difference you'll learn early on in the game (if you don't already know). All the fonts are noticeably different so whichever you choose will lead to a different kind of pairing. Whether you fail or succeed in creating a happy couple, you'll end up with plenty of information about your choices and learn a little bit more about pairing typefaces in your designs.
All the fonts and pairings are designed to teach broader principles through specific examples, and you can play again to make different choices and learn more. Even if you happen to be pretty good at pairing your typefaces, it's worth failing to learn why certain choices don't work. The information you'll learn from failures of font love can be just as valuable.
Overall, Type Connection is a cute and clever way to teach you quite a lot of useful information about how different fonts and type styles affect your designs. If you're looking to learn from scratch or just brush up your skills, it's a really fun (and free) way to do it.