How often I cry tends to zig-zag. I'll usually do so after having a bad day, feeling frustrated with something going on in my life, or remembering an unpleasant memory. But in a more positive way, I might also cry if someone tells me something that's really nice and touching; while I consider myself relatively nice and do my best to treat everybody well, it's pretty rare for anyone to actually return any kindness to me and it makes my day when they do.. Life situations are pretty much the only times where I'll cry, since I don't have many emotions otherwise, and have developed a bit of a tough skin as a result of having a fairly bumpy life. When my friends tell me that they feel like crying, I honestly encourage it most of the time; it's never any good to bottle up your emotions if you don't have to. Considering it's a natural response to stress, it should never be considered a sign of weakness, in my opinion.