Some details changed for privacy, just in case. A (quite handsome, in my opinion) friend of mine is going through a rough patch and a few weeks ago we were hanging out late after everyone else had gone home. I knew he was struggling, so we've talked a few times pretty intimately. He started to talk and then dropped his face into his hands and started to sob, kind of rapid and quiet. I went to sit next to him and asked if I could hug him, and his response kind of just came out as another sob, voiced this time, so I put my arms around him and laid my head on his shoulder. I could feel his shoulders shaking as he kept crying, voiced and more intense sobs. After a moment, he wiped his eyes and apologized, and I told him that he was fine and then we talked. He teared up a few more times, but that was it. It was short, but really really nice - he's cute and an attractive crier, so unfair.