From the comments thread on the first post of today:
If you have kids try this game that I came up with by accident about 10 years ago: get their yearbook and draw someone, and then give them the drawing and the yearbook and see if they can figure it out. It's a fun game! We were playing last night and even cynical high school kids love it.
Even without kids! This is a great game and great as a drawing project.
You just need something to draw. Once, years ago, I came across an ad that had a collection of photos of smiling realtors. I still have those drawings somewhere, but I got really inspired trying to capture what felt to me like the insanity of their smiling. I wrote statements of their inner thoughts, explaining those facial expressions.
So that's a variation of Ryan's game — which I love as a game. Pick a face to draw, exaggerate the expression, and write out an imagined statement that somehow goes with that face. A way to do that with another person is for both to draw the same face and then see how differently you interpreted it.
Another thing I used to do — often with another person — is to watch some TV talking heads show — the news or whatever — and pause the TV on some interesting facial expression and draw the face. Add a snippet of what that face said, and feel free to make it as absurd and out of context as you like. Now, it's timeless art!