Due to real life stuff, almost never. Last time I really cried was well over a year ago (I had one little episode during a bad panic attack but that was like... three tears. Doesn't count.) Don't get me wrong, I'm not trying to be some macho man, I very often WANT to cry and just can't.

Like Pike, media makes me cry much more easily. Still not exactly a lot, but there are a few things that will do it every time, like the last episode of Babylon 5 or Johnny Cash's rendition of Hurt.