I think having anyone tell you to smile more in any situation that isn't a posed photo is creepy because it's invalidating your emotional state, or telling you to stop feeling your feelings and replace them with how the other person wants you to feel... the most fucked-up instance of this that's happened to me was when a female therapist suggested "smiling more" as a prescription for depression.

All that aside, I have actually been catcalled on the street by women, and since it doesn't happen to me all the time I just found it funny. I have also been complimented in the office on my appearance by a female supervisor and it felt creepy, but had much worse sexual harassment from a male boss who apparently wasn't even gay, just doing it to mess with me.