If you had a friend that woke up from a 20 year coma, what first would you tell them?

This depends on a lot of things - namely the mental and emotional state of the said friend. Stuff like "welcome back" and "I'm glad you're alright" are pretty much a given, so I'd think that this topic is referring to what you'd say after that.

I'd think that they would first want to hear personal things, how their family is, their partner, whatever. Political things like who the president is and events like 9/11 aren't really important until they're out functioning in the world (unless they had some kind of direct effect on him - i.e., his/her brother was killed). A lot of other things seem rather trivial when you get down to it.

I couldn't imagine what missing out on two decades would be like, or catching up with the world. Just how long would that take...? =/

Jam it back in, in the dark.