This piece on Jezebel really struck some chords, both in itself and because of some of comments from women sharing their experiences. Really, guys, telling a strange woman-- or even an acquaintance or co-worker-- to smile is a creepy thing to do. No need to feel bad about it, just read for some explanation and then please try to not do it. Some perspectives:
Men who ask this question don't want to know the answer. They want to disarm you. They want you to think, "Oh dear, I didn't even realize that my sourpuss lips were putting a damper on this poor gentleman's day" and guilt you into making a conscious effort to be nicer - ideally, to the man in front of you, who has shamed you into being nice in the first place. It's Move #93 in the playbook for how men take advantage of women who have low self-esteem and that's what pisses me off about it.
Also, fuck you, I look mad because my face is naturally downturned when I'm not smiling. (Thanks for the reminder, btw.) Plus, do you really expect me to have a perma-grin plastered on while I'm doing menial data entry on my computer?
I'm not smiling because I'm thinking about the fact that men think of women as decorations, without inner lives.
There was this one time where I'd just come from the doctor's office where I'd been diagnosed with an ectopic pregnancy and injected with chemo drugs to "dissolve" that pregnancy. I'd just lost my fucking baby. I hailed a cab to get home, and the driver harassed me for at least 10 minutes, asking why I wasn't smiling, to smile because I'd feel better. I told him I'd got some really bad news. Didn't deter him in the least.
It's none of anyone's damn business. Stop telling people to smile when you know nothing about them.
Sometimes I get this gem from guys at parties/work, and it was immensely satisfying when I came up with a response.
Creepy Guy: "You know, you'd be pretty if you smiled more."
Me: "You'd be smarter if you kept your mouth shut."