Some Personal Questions You Should Never Ask

The best thing about getting married is that nosy acquaintances stop asking you, “So when will you two get married?” The worst thing is that they start asking you, “So when will you two start having kids?”

Modern society has somehow let a certain kind of rude question slip through the cracks: the friendly inquiry into someone’s progress reaching traditional life milestones. These potentially fraught questions are often treated as light conversation starters by co-workers, distant relatives, and acquaintances. We’ve explored how to answer those questions, whether politely deflecting or addressing an underlying emotional issue. Now let’s dive into what not to ask in the first place.

Inappropriate questions are almost inevitable. Small talk is about getting to know people, and it’s impossible to predict everyone’s personal boundaries. And it can be satisfying to intentionally enter a more meaningful conversation. The important thing is to realize how seemingly banal questions can hit sore spots.

“Having good etiquette is all about making others feel comfortable and respected,” says Myka Meier, founder of New York’s Beaumont Etiquette school. “Therefore, before you ask a question, think how the other person could feel. Any question that may cause someone to feel under pressure, uncomfortable, self-conscious or judged is one to steer clear of.”

Relationships and family

“When will you two finally get married?” might seem like an innocent, jokey question. But what reply do you expect? You’re not asking for a heads up; when someone’s engaged, they’ll surely tell you. It feels more like you’re grilling them for opinions on the institution of marriage, or implying their relationship looks stale. Neither is an appropriate conversation starter.

If you want to ask about the relationship, start with something more innocent. If you open with a vague “How’s your partner?” you can let the other person decide how intimately to answer. Or open up about your own life, but don’t demand they rise to meet your level of intimacy.

“When are you two going to have kids?” is even worse. The reasons for not having children are myriad, personal, and sometimes unhappy. The honest answer might be “Things have been hard after last week’s miscarriage” or “Turns out the adoption agency is kind of racist,” but unless you’re a close friend, the person you’re asking will have to make up a more innocent answer, distancing themselves from you without you even knowing. “Instead,” advises Meier, “you could ask someone ‘So tell me about your family’ and even if they don’t have children, they can still tell you where they are from or about their relatives.”

When talking to someone with kids, avoid judgment calls like “When are you going to have more?” or “Did you want a girl instead?” Just ask about the kids that do exist: How old are they, what are they like? Don’t ask what milestones the kids have reached; the last thing any parent needs is another person testing their kids.

Pregnancy

It’s pretty obvious why “Are you pregnant?” doesn’t fly. You really can’t be too cautious. I’ve chatted with a friend in her eighth month and still waited for her to bring it up first. Still less awkward than a false positive.

For the same reason, if you know someone’s pregnant, “Are you having twins?” is out of bounds. If they are, they’ll definitely mention it. When you hear the due date, believe it. Work very hard to avoid the merest hint of implying a pregnant woman is fat—or obsessing over how skinny they are. Just avoid any implication that you’re evaluating their body.

If they tell you the baby’s gender, react positively, but don’t treat it as a “win” (unless the parents are already openly doing so). When a colleague of mine was pregnant with a boy, several people asked “Is your husband happy?” One even congratulated her on “doing her job,” as if she were producing a male heir for Henry VIII.

Don’t start in on child-rearing plans. “Are you going to breastfeed?” or “Are you having a natural birth?” are weighty decisions, and any advice you have to give is definitely better explained by a dozen parenting books, and contradicted by a dozen others. The only appropriate advice is entirely optional, free of value judgments, and focused on making the expectant parents feel better and freer. People have and raise babies all kinds of ways, most of them work just fine, and you’re not the bold thinker who will unlock the secrets of SIDS.

Work

“Do you like your new job?” isn’t that rude, but it can be awkward. If they don’t like their job, they’re probably not telling everyone, so you’ll be forcing them to lie. Just rephrase in a way that doesn’t demand a value judgment. “What’s your job like?” or “What are you working on?” is a little easier to answer without a deep soul-search about career fulfillment.

Checking in on a longterm project is another grey area. “How’s your book/podcast/side business coming along?” feels like you’re requesting a progress report. Instead, ask about any specifics you learned, or follow up on anything they’ve posted about the project on social media. That way you’re approaching the parts they’ve already chosen to show the world, which is likely a lot more interesting to you than what percentage of work they’ve completed.

When first meeting someone, even the most common opening question can be risky. Meier advises against opening with the old line “So what do you do?” as it can sound opportunistic. If your goal is to get to know someone better, that question only works if they happen to like their job enough to talk about it in their off hours. (Even worse is the loaded version I got at a tech conference: “What do you make?”) If you’re starting out cold, “What do you do for fun?” is a lot more useful. By definition, the answer is something the other person wants to talk about.

If you know someone is between jobs, the best-intentioned followups can sound like nagging. As The Muse’s list of rude job-search questions demonstrates, this is a minefield. People struggling to find work can feel like the world is calling them worthless, and feeding into that won’t win you any points. Avoid making suggestions like “Have you thought about going back to school?” You’re not going to be the one who convinces them to change course or settle. Even a simple question like “Where have you applied?” sets up an expectation that you’ll check in later for a progress report, says The Muse. If you really want to help, instead ask what they’re looking for. And be cautious if you suggest any leads; leave them plenty of room to politely turn you down.

Use your judgment

Most of the questions above are appropriate in certain contexts: among partners, close friends, or immediate families. That’s one reason they’re so inappropriate for small talk: they insinuate intimacy and ask for vulnerability. By asking for a progress report on someone’s life, you’re also asking them to evaluate your relationship to them.

We naturally want to increase the intimacy of some relationships over time, so we can’t avoid testing the boundaries. But by paying closer attention to the latent meaning of your questions, you can match them to the context of the relationship. As Meier advises, “Before you ask a question, gauge its sensitivity level.” If it’s a lot more sensitive than what you and your acquaintance usually talk about, save it for another time.