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When I was 18 or so, I was asked by one of my grandfather’s pervy law partners if I intended to get by in the world on my smarts or my looks. Of course, I would have loved to have glued his mouth shut, but I also kind of appreciated the reveal: Anyone stupid enough to underestimate me is the one at a disadvantage, not the other way around.
I do believe that this dumb little comment was meant to be flattering, but instead it underscored that complimenting anyone has always been a tricky endeavor. In the years since this exchange took place, the etiquette surrounding compliments—or what we think of as kindly words—has been overhauled, and offering praise today seems more trip-wired than ever. Does every “God, you look amazing” suddenly come across as a judgmental “Are you on Ozempic?” Is it best, these days, and especially this holiday season, to just keep well-intentioned comments to yourself?
“I like to think I’m very supportive and enthusiastic about others’ life wins: new jobs, new husbands,” says Lauren Santo Domingo, the New York–based co-founder of Moda Operandi. “But I do feel as if I put my foot in my mouth sometimes. Just the other night I congratulated someone on their divorce. It was not a mutual split. Oops.” She has also occasionally been on the receiving end of misfires, such as when someone recently asked if she’d gotten a facelift. (“I hadn’t,” she clarifies.)
One must when it comes to delivering a backhanded compliment, or what is sometimes called a velvet dagger, it’s best to appear sincere. “Bless your heart” hits only because you might actually mean it. Slim Aarons – Getty Images
According to some etiquette experts and advice columnists, if a friend suddenly looks surprisingly glamorous, suspiciously youthful, or unusually aerobicized, you must keep your lips zipped. You must never ask them to let you in on their secrets, the experts advise, and they generally warn that telling someone that she looks incredible might make you seem like the Harvey Weinstein of the holiday party. (In fact, some columnists even arm readers with dreary lists of compliment retorts, including: “My appearance is the least interesting thing about me.”)
This may seem like a frivolous issue, but I don’t think it is—at least not entirely. What gets lost in a landscape in which we’re told that we can’t express sincere admiration without fear of making a grievous misstep? On the other hand, has some good come out of this cultural reexamination? I turned to friends and colleagues for their opinions, and it turns out I’m not alone in grappling with the new social restrictions.
Some argue that the reassessment of compliments in recent years largely serves the greater good by making us more sensitive and sensible about how we comment. Writer and television producer Susan Fales-Hill says that after years of weathering microaggressions, she welcomes more thoughtful approaches; she adds that she errs on the side of caution when giving compliments herself.
“As the product of a mixed marriage and someone who grew up in the pre–politically correct 1960s and ’70s, I’ve been on the receiving end of my fair share of condescending comments masquerading as compliments,” she says (she cites specifically the dreaded “You’re so articulate”). Doing away with patronizing digs like this, she notes, has contributed to the “betterment of us all.” However, a recent experience made Fales-Hill think that there has to be a happier medium.
“One evening I was leaving an event with a friend when two gentlemen standing 10 feet away from us very tentatively ventured the words, ‘Excuse us. We don’t mean to be rude, and we hope you won’t be insulted, but is it all right to say that you ladies look lovely this evening?’ It wasn’t as if they’d called out, ‘Yo, got a burger to go with that shake?’ ” The men were clearly afraid of being perceived as sexist pigs and were expecting total hostility, she says, but something still compelled them to offer the compliment anyway. “That’s when I knew we’d reached a sad pass in our society,” she adds.
Perhaps compliments seem more fraught these days because face-to-face human interaction in general has become more fraught. Thoughtful exchanges are getting rarer in an era when many of us can’t even be bothered to use actual words and instead transmit witless strands of emojis in DMs.
If you’re planning on delivering a withering remark remember that you’re insulting someone, so if they catch you, don’t backtrack. Instead, wink and say, “You’re sharper than you look.” Bettmann – Getty Images
“We’ve lost so much because everybody’s on their phones and no one’s speaking,” says T&C contributing editor Cornelia Guest, no stranger to social mores. All that texting “makes us less articulate in person and less confident in communicating with someone. We lose humanity, in a way.” Tone remains a decisive factor in determining whether a compliment is received with enthusiasm, awkwardness, or horror. “When you speak to somebody, you get a lot more information,” Guest says. “You can look at their eyes; you can hear the tone of their voice.”
It seems that a few of the old truisms have remained intact during the compliment reckoning. The first: Sincerity is crucial. Always has been and always will be. Praise should “genuinely come from a good place, and be well intentioned,” says textile designer Lisa Fine, who tells me she has not restricted the way she gives compliments at all in recent years. If someone has had a physical transformation, she’ll offer praise. “I just believe in being sensitive, kind, and honest.” But as for compliments that are “snide and backhanded,” she says, “anybody can sniff that out a mile away.”
All of the women with whom I spoke seemed to believe that the giving of compliments remains a defensible practice, and several say that offering praise may be more necessary than ever. “I think there are not enough positive things said in this world,” Fine says, “and if it’s taken wrong, it’s taken wrong.”
I largely agree. We live in an era of vicious, unrelenting schadenfreude, and undercutting our ability to make one person feel admired in an age of degradation seems mean-spirited. As a kid I was told that it was a sign of a strong, generous, and self-assured character to be able to offer another person heartfelt congratulations and admiration. Maybe the key is indeed sincerity, or maybe it involves keeping compliments broad rather than sailing in with an ask for a reference to the person’s dermatologist or divorce attorney. More than anything, it’s probably just a question of correctly reading the vibe—another social skill that should never be allowed to sunset.
If there’s one thing we can all agree on, however, it’s that anyone who trots out the “least interesting thing about me” line above likely won’t have to endure expressions of admiration very often.
This story appears in the December 2025/January 2026 issue of Town & Country. SUBSCRIBE NOW
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