I've had a number of observations over the past couple of months. Here are the ones that stand out:
First of all, my BF and I got engaged a few months ago! I guess I should start calling him FI on here, although he will be my husband quite soon.
Anyway, there have been a fair number of tears around here lately, mostly because of a string of rotten luck. I've also just felt more comfortable crying around FI than I ever have around another person, and I think that prompts me to do it more easily.
So, here are some of the most memorable incidents.
1. I'll start with one about a friend. A major, unpleasant event occurred that upset FI and me, but our friend (male) was even more upset by it. We were meeting him in town, and we knew he'd be very emotional (he'd been texting us the night before that he was very broken up about everything). As we walked toward him, he referred to an inside joke of ours, and I pulled the three of us into a hug. I figured it would be a fairly quick hug, since we were on our way to a meeting, but he wasn't letting go, and he suddenly began to sob. His sobs were fairly loud, and his whole body shook. The three of us squeezed each other harder, and we stood there hugging for about two minutes while he sobbed. Both FI and I had tears in our eyes when we pulled away, and our friend removed his glasses to wipe his face, which was covered in tears. He continued to cry on and off for the next half an hour while we discussed the events, attempted to get back on track, etc.
2. Several days ago, FI and I had to confront a very emotional decision (which ended up resolving very nicely, surprisingly). A lot of things were completely out of our control, and we were both upset about it, but I was definitely more anxious and distressed than he was at the moment. We were lying in bed, discussing the options, and I began to sob. We were both lying on our backs, and he said, "Let me hold you." I rolled over onto his chest and sobbed into his shoulder. This may be the hardest I've ever cried around him - I was really quite upset. He held me tightly for about ten minutes. I was definitely doing a large lip curl, and my whole body was shaking. After I'd calmed down a bit, and we talked more, he started to sob a little bit too, and we just held each other until we managed to fall asleep. The next morning, we were both tearing up, and when he left for a couple of hours for a job, I cried on and off the entire time he was gone. When he got home, we talked again and resolved a few things. The whole situation was in our control and resolved a couple of days later, fortunately, but it was a scary weekend.
3. One of FI's family friends recently passed away. We knew she was ill and were sort of expecting to get the news, which we did one morning via email. I was working on a project across the room, and he told me he'd just gotten word that she'd died. He made reference to a bit of an inside joke of ours (we definitely use humor in somber situations quite often), but I knew he'd be upset. Not devastated, since they weren't extremely close, but still affected. I set down my things and came over to the couch to give him a hug. He was still reading the email, and his lips began to quiver. I gently took him in my arms and closed the laptop, and he curled up on my chest. He let out one breathy sob and laid there in silence for about a minute. He finally sat up, and his face was streaked with several tears. I wiped/kissed them away, and we talked about her for a few minutes. I had to leave for work then, but he definitely seemed less upset - again, he wasn't devastated by this death, so I think the opportunity to let out a couple of tears and talk about her a little bit was enough for the initial expression of grief.
We went to her funeral several days later. Of course, there were a number of people wiping away tears, but as this wasn't an unexpected death, it was more a celebration of her life than a time of intense grief. One of the eulogies, though, was particularly direct and emotional, and both FI and his sister were in tears through most of it. It normally would have moved me to tears, as I find myself personally affected by similar things since my mother's death, but I was definitely in "comforting" mode. I had my arms around FI, and he, his sister, and I were all holding hands tightly. His father was also wiping away the occasional tear. After the eulogy, I wiped away the tears on FI's right cheek, and he blew his nose with a handkerchief.
This was the first funeral we've been to together, and somehow, it felt as though the whole experience brought us closer together (even though it was for an unfortunate reason, of course).
4. This one is possibly the most interesting: FI and I have begun to explore roleplaying comforting/crying. The other night, we concocted a scenario in which we'd met at a bar after he'd broken up with a GF, and he'd come back to my place and allowed me to comfort him. It was a LOT of fun. It was a bit impromptu, since we'd just planned to discuss it and ended up actually trying it out. But he wants to try it again and explore other scenarios, which I think sounds great. His fake crying is actually quite good (he's done a bit of acting).