I've been holding off on posting this for a while, but the board has been so quiet I figure now's as good a time as any. 

I have a 21 year old male coworker (looks strikingly like [url=https://img.buzzfeed.com/buzzfeed-static/static/2016-07/27/4/asset/buzzfeed-prod-fastlane02/sub-buzz-10514-1469609672-7.jpg?downsize=1040:*&output-format=auto&output-quality=auto]this[/url]) who I have always wanted to see cry. He has depressive tendencies and once mentioned to me that "I've felt like crying every day this week" as well as a couple old tweets along the lines of "worst night in a long time," or even more tantalizing, "I hope the tears in my eyes don't let on that I'm upset to my coworkers." (I checked the date, I wasn't working that day.)All that makes him sound sort of attention-seeking, but that's really not the case at all. He's someone who routinely puts the needs of others ahead of his own, even to his own detriment, and tends to be very stoic, if a little morose. He also has a lot of ideas about masculinity that I think end up hurting him. 

A few weeks ago his family pet was having medical issues, and he came into work anyway. I approached him in our break area around midday to ask if there was any news. He was facing away from me, and said quickly, "yeah put down," like he was already fighting tears. I said I was so sorry, and asked if he hugged (it's a habit of mine to ask before hugging someone, especially if I have no hug-history with them), and he said no. He was already trying so hard not to cry, I think hugging him would have made him break down. His chin was trembling and his eyes were filled with tears, he kept touching at the corners so keep them from falling. He said, “life is so cruel” and the pain in his voice and on his face was so open, that might have been the most vulnerable I've ever seen anyone. I sort of wish I had hugged him anyway, even though it almost definitely would have pushed him over the edge. 

He said, “I can’t cry, like an a**hole” (or along those lines), said that his friend had just lost his dad and what right did he have to cry when other people had it so much worse. I tried to combat that with “What would your friend say if he heard you say that? You crying doesn’t take anything away from anyone else,” but there wasn’t much I could do to dismantle that line of thought quickly. At that point other people came into the room and I stepped in front and talked to them so he could stay back and compose himself. I figure that's the second-best way to help someone who is crying, who isn’t willing to accept direct comfort. I can at least make it easier for them to stay discreet. 
Later that day we walked out to our cars and he mentioned working on some project for our boss that evening and I said, “tonight’s going to suck. It just is.” He said he wasn’t going to go home and was going to try to just keep busy. I said okay, but make sure you let yourself feel it sometime. He said, “I will, when I’m alone or late at night.”

I held off on posting this because the reason he was crying was so sad. In happier news, his family now has a new puppy, and a few of us at work had a tree planted in a national forest in his old dog's honor.