…[W]hen presuming that nothing could possibly be that bad in an attractive woman’s life that she dare not smile, you are dehumanizing them. It’s a “nice” form of dehumanization, but it’s still dehumanization nonetheless. It’s also transparent. You don’t see men running up to homeless women and the elderly and asking them to smile. The request is usually made when the requester thinks the requestee is attractive. It’s not about a legitimate need for women to be happy as much as it’s that smiling/pleasant-looking women are easier on the eyes and more inviting to approach. It’s really not about the woman at all.
If you really are that hard-pressed for a woman to smile, tell a joke, slip on a banana peel, pay her phone bill; basically, instead of asking a stranger to fake an expression for you, do something that might legitimately brighten her day. Who knows, she might even smile. And, she might not. You have no control over that, and that’s kinda the point."