Of the categories mentioned so far, I can recall having seen guys cry live in person at the following:  Funerals, Weddings, Buses (station), Theaters (actor)

I remember having seen women cry in person at Airports, Parties, Weddings, Movie Theatres, Hospitals

I'll admit to having offered guys drinks at parties and bars in hopes to increase my chances of seeing them cry, but no results, so I gave it up a long time ago.  I don't think guys really cry at parties the way girls seem to do.  If they do, they were probably going to cry anyway, no matter where they were.  Save your money for your own drinks. 

One of us should advertise our services to be some kind of "coffee and snack supplier" for support groups, haha... you know, come for the treats, stay for the crying? 

If only!!!!!

This is a less common thing, but I've seen it more times than I would expect: Crying in a parked car, in a public parking lot.

War memorials