I've sung for friends (in fact, one old friend constantly sings, so if I'm around her, I pick it up and do it for the next like three weeks), in front of the school, at a party, just for the heck of it, ect. Personally, I think I suck at singing, but whatever; I've embarrassed myself enough as it is, more won't hurt. I'd rather play the piano or guitar if I have to sing, but that's not always an option.
So, if I was asked, probably. But chances are I'm not going to start singing randomly, and if I do, it's just for fun, and I'm goofing off.
Not that I'm a guy though. But the songs I do sing are almost always originally performed by males (my voice is deep enough that I do those better than female ones), so that might be problematic if the pronouns aren't changed.
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"Nothing worth having is easy."
Three years!