Dear Etiquetteer:
A woman friend on [Insert Social Media Platform Here] asked her female friends how to tell the difference between a guy being complimentary and creepy. As a man I wonder about the difference as well. I suppose it makes a difference if the parties are both single and romance is a possibility. But what if a friend is looking particularly sexy? How does a friend, not looking for romance, comment? Or is it creepy to comment at all? Does age difference matter? What matters?
Dear Complimenting:
Just to clarify, we’re talking about comments exchanged between People Who Know Each Other and not Total Strangers. The catcalls of construction workers to female passersby are obviously Not Perfectly Proper and don’t play a role here.
The real difference in whether a compliment is actually complimentary or not is in how it’s received. If its impact is creepy, then it’s creepy, regardless of intention. Often what makes a compliment creepy is how it’s delivered. If there is a suggestive tone in your voice, a leering look in your eye, if you’re standing too close, those things all increase the Creep Factor.
Ask yourself how you want to make this person feel. Do you want them to feel good about themselves and their appearance? Do you want to encourage them to wear more of that color or style? Do you want to convey an interest in, um, getting to know each other better? You see where this is going. It’s the difference between “You look desirable” and “I desire you.” How you deliver it can change the impact. But, as Etiquetteer’s Dear Mother used to say, “When in doubt, don’t.” If you’re not sure how a friend might like hearing you tell her about “looking particularly sexy,” best to keep mum.
Etiquetteer is sorry to say that the age gap does make a difference. The older a man is, the more suspect his motives are likely to be. One thinks of elderly, devious Charles Laughton in The Paradine Case making young, beautiful Ann Todd visibly uncomfortable* as he says “You look very, very appetizing tonight, my dear.” You can tell he’s ready to gobble her up, and not just because of the word “appetizing.” There’s a reason for the Lecherous Old Man stereotype: he actually exists. And Etiquetteer knows it, having run interference for years for young ladies who have been creeped out by them.
Etiquetteer will conclude with the age-old advice that a Gentleman never forces his attentions on a Lady.
*Not only that, her husband, Gregory Peck, is in another part of the room.