Well, I still haven't had a full-out crying obs of my boyfriend, yet, but I came closer than ever this past weekend.

The two of us were at a party, and he was a little drunk (but still all there).  We were sitting on a bench together and all of the sudden he started cuddling me and talking to me about some things that we've been needing to talk about for a while now.  After a bit of that, he went to put a shirt (he had multiple) in his car and asked me to come with him.  We ended up sitting down on his back bumper, and he started getting into some more personal issues he hadn't wanted to bring up with our friends around.  We were sitting right up against each other with all four of our hands clasped together, and I think our heads were together.  I know I couldn't see his face, but his head was facing downward and I could see his glasses out of the corner of my eye.  While he talked, I heard his voice grow emotional, and I thought I saw something (tears?) fall into his glasses, but I couldn't be sure.  By the time we returned to the party, he was obviously fine, but before we separated in the crowd, he leaned over and kissed my cheek, and I noticed afterward that my face was wet where his glasses has bumped me.  

He ended up getting drunker as the party went on and got really sick by the end of it.  I've never drank or seen someone quite as sick as he was that night, so this might be usual, but I noticed that he was also shedding tears then.  After he threw up the first time, he sat back, unconscious, and I could see a tear streak running down from the corner of his eye.  Once I got him fully awake, he left his head hanging over the bowl I had for him, and I could see tears falling directly from his eyes and sometimes dangling from the tip of his nose.  The presence of puke made it a little harder to enjoy this part, but it was still nice because I was the primary one to take care of him and I got to help him out and hold him all night long.