If you can’t say something nice—or your message reeks of “I told you so,” concerns a teenager’s clothes, or is only going to create a headache on Facebook—don’t say it at all. These experts know what they’re talking about.

By Rebecca Webber
Updated December 28, 2015
Ben Wiseman
Ben Wiseman

When You're Not Sure What to Say

My dad passed away when I was in college. I was taking an exam shortly after it happened, and I couldn’t focus. I picked up my backpack and walked out of the class. The teacher said, “If you leave, you’re going to fail this test. That’s going to hurt your average. I’m not sure you’ll pass the class.” I just kept walking. My dearest friend, Peggy, picked up her backpack and followed me out. I walked to this place called the Duck Pond, where it was just very mellow. I sat on a picnic table, and she sat next to me, without saying a word. I’ll never forget it. After about five minutes, I looked at her and I said, “Oh, my God,” and I started talking about my dad’s death. Now, if she had been asking me, “Are you OK? What do you need?” I don’t know if it would have worked. We both just sat quietly. Sometimes you just need to stop talking, because in silence, the truth comes out.
—Hoda Kotb, cohost of the Today Showand the author of Where We Belong: Journeys That Show Us the Way. She lives in New York City.

When Someone Is Wrong on the Internet

Some social-media conversations always turn into arguments. I rarely discuss politics. And you couldn’t pay me to get involved in another conversation about vaccines. I’ve done it, and it doesn’t matter what facts I pull out. I’m not going to waste my time. If I’m tempted to comment, I call to mind one of my all-time favorite cartoons, from the web-comic xkcd.com. A guy is sitting at the computer, and his spouse says, “Are you coming to bed?” He says, “I can’t....Someone is wrong on the Internet.” That always helps me laugh at myself and back away from the conversation.
—Amy Vernon, a digital-media consultant and a social-media etiquette expert who tweets under the hashtag #smetiquette. She lives in New Jersey.

When You Told Him So

Something goes wrong, and you say, “Didn’t I warn you? Didn’t I tell you this was going to end in disaster?” At some point later on, you might say, “Honey, maybe we shouldn’t ever do that again.” But hold your tongue on gloating. As Gloria Steinem says, “The truth will set you free, but first it will piss you off.” It can make other people bitter or resentful or hurt their feelings. If these are people you love, a little diplomacy, a little tact, and a lot of silence go a long way.
—Judith Viorst, a poet and the author of Alexander and the Terrible, No Good, Very Bad Day. Her latest book is Wait for Me: And Other Poems About the Irritations and Consolations of a Long Marriage.She lives in Washington, D.C.

When It’s TMI

Don’t be the person at the office who shares too much: the one talking about his visit to the winery with his wife—perfectly reasonable—and all of a sudden he’s telling you how he got stinking drunk and what happened next. When you expose those kinds of details, it allows other people to form a judgement about you. Even sharing specific parenting challenges allows others to make a judgment about your capabilities. It might be completely inaccurate! But it can still impact your career. If you share a controversial opinion, you could be fine if the other person agrees. If not, it could be a death knell.
—Edward Yost, the human-resources business partner for the Society for Human Resource Management. He lives in Centreville, Virginia.

When Someone (a Teenager) Is Pushing Your Buttons

In politics, we say, “You can never get in trouble for something you didn’t say.” In my most disciplined days, which are few, I have managed to apply it to two of the toughest terrains known to mankind: marriage and raising teenage girls. Like political opponents, husbands and adolescent girls are scholars of pushing one’s most delicate, hair-trigger buttons, sometimes making us utter things we regret—and that will be used against us later. But if you must say something in the heat of the moment, here’s a lesson of advanced politics: Shoot the king; kill the king. You had better be right.
—Mary Matalin, a political consultant who has worked for presidential and vice-presidential administrations. She lives in New Orleans.