On the last day of the Olympics my boyfriend cried four times over the course of the day. This was only my second time seeing him cry, and I'm going to mainly focus on my reactions to it, because he's a really private person and I want to respect that.
It's weird, he is not really a big crier, so this was a very unusual event for him. Partly his crying was spurred by the end of the Olympics, and the end of things just makes him really sad and reflective about how things will be different in two years. Which I think is.....just adorable. So he cried for a couple minutes around noon because we were sort of having a disagreement on top of both of us already feeling bad.
Around mid afternoon it was my turn, I cried pretty hard for maybe 10 minutes because I was just feeling totally hopeless about a lot of things. He tried to be there for me but he was pretty paralyzed by his own emotions and problems. Then again in the early evening, with his head in my lap, when we started watching the closing ceremony. I wiped away one of his tears for him then, and just stroked his head for a long time.  Around 11:15 I suggested we get in bed and end the miserable day, but he needed to talk a walk to calm down. So we walked around outside (it was very cold), I held his hand the whole way and I saw he was fighting back tears. When we got back to his apartment he sat on the couch without taking off his hat or jacket and cried a little more. I took off his hat so I could run my fingers through his hair some more (that's very soothing for him).
After five minutes or so he gets very businesslike and suggests we take out the recycling (excuse for another walk), so we do that. Then around 12:30 we finally get in bed and he starts crying again almost immediately. This time he's sobbing, quietly, but it's still harder than I've seen him do before. He's turned away from me, so I reach around and stroke his face, and he presses into my hand. I ask him, "can you come closer?" He does, and I say, "Thank you," as gently as I can. I feel an enormous need to be as close to him as possible, to try to smother out his pain, and the only thing I can think to do is lie almost on top of him and hug him. I was not able to solve his problems, I just wanted him to feel okay enough to get to sleep. I started talking to him once the worst of it had subsided.
"You don't need to make any decisions tonight. Just lie here with me."
"Just try to relax your whole body." I asked him to relax his legs, his jaw, his eyebrows, his mouth, all the places I know I get tense when I cry. I told him he was safe, and to just focus on the moment, lying next to me. I asked him to relax his jaw again. I asked him to take a deep breath. He did, and I said, "Good job." I was really really sleepy, but I wanted to stay awake until he fell asleep, which he did eventually. He wanted to be held throughout the night, which I was happy to do.

The next day my car broke down right by his house (an hour away from my house), so I basically lived out of his place for the week until my car was fixed. It was stressful for me, but it turned out to be a really great experience because we got to "test out" what it would be like to live together. And let me tell you, it was awesome.  I was really happy we got to do that, because I would have hated to go to work the next morning and be unable to balance out that awful day with good days.