Each artist’s unique interpretation of form and space, along with the context of their recent work, leads them to produce type designs that are different but related.

So find a good type designer whose work inspires you, then play mix-and-match with some of their designs. It’s a simple approach but fun and effective.

Also, I saw that A Book Apart is going to release a typography book later this year. Their publication are awesome. http://www.abookapart.com/products/on-web-typography

Thanks for the feedback. We are indeed considering ways to help our users pair fonts better. You can also check out the About Face articles (http://blog.typekit.com/category/about-face/) for good pairing suggestions. Often when we release new fonts we also show off some good pairings (http://blog.typekit.com/category/new-fonts/).

I completely agree. As paying customers, we need more of these articles. Especially for those of us that are type challenged (ME). Also, I would like to see Typekit implement some kind of font pairing system where you can test multiple fonts together.

To avoid unnecessary head scratching a different example character should be provided as an example of aperture:

“Also, try to pick typefaces with similarly-sized apertures (the partially-enclosed parts of letters, e.g. in the letters a and c)”