How to tell if a question is appropriate
Asking questions is usually a means to an end. You need information, the person you’re speaking with (hopefully) has answers. However, while this works great for “What time does the store close” or “What is your favourite book?” it gets sticky when you veer into personal territory, says Sarah Epstein, MFT, a relationship therapist. Many people may think they’re just making “polite conversation” by asking questions of the other person but they are actually coming across as intrusive or judgmental, she says.

How do you know the difference? “A good rule of thumb is that polite people always think about the impact of their words instead of only thinking about the information they want to learn,” she says.

You’re so cute, why are you still single?
“Thoughtful, polite people don’t ask about a person’s relationship status because they know that it can be a sensitive subject for many,” Epstein says. The other issue with this question is the word “still” – something you should try to avoid because it comes across as inherently judgmental in any personal question, she adds.

Why don’t you have kids yet?
Polite people never ask about reproduction because they know that a person’s choice whether or not to have children can be a very touchy subject, laden with potential landmines, Epstein says. “These types of questions often lead to hurt feelings, particularly for those who struggle with infertility or those who have chosen not to have children but continually receive questions about their decision,” she says.

You look so thin! Have you lost weight?
For many people this may seem like the ultimate compliment, acknowledging someone else’s hard work. But unless you know for sure that the person was trying to lose weight and that they are OK with you commenting on their body, steer clear. “Polite people avoid questioning or commenting on others’ weight at all,” Epstein says. “Superficial questions rarely lead to fulfilling conversations. Plus weight loss can have many sources, including illness, eating disorders, anxiety and grief.”

Why haven’t you put a ring on it yet?
Even in couples who’ve been together for years, not all relationships lead to marriage and not all partners are looking to be wed, says Jodi R. R. Smith, etiquette expert and founder of Mannersmith. “The only people who should be asking these questions are the ones in the relationship,” she says. “If you just want a reason to attend a big party, you should host one yourself (after the pandemic, of course).”

You seem like you’re doing well, how much money do you make?
The only people allowed to ask this question are professional headhunters doing a confidential salary survey, Smith says. “If you are just curious how much your friend, cousin, or neighbour makes at their job, you can quell that curiosity by looking it up on a salary website,” she says. “Many etiquette rules have relaxed but asking about money is still tres gauche.”

I’m sorry to hear your dad passed, how did he die?
Curiosity about someone’s death is natural and very human, especially during a pandemic of a deadly virus, but this is still one question you shouldn’t ask, Smith says. “You need to remember that the person you are talking to is in mourning and that’s no time to play amateur detective,” she says. “You should be expressing your condolences and looking for ways to comfort the mourner and that’s it.” Plus, there are generally kinder routes to finding that information (like Google) that don’t put the burden on the family.

Why do you look so tired?
You may think you’re expressing concern for their health and wellbeing but what the listener likely hears is “you look bad,” says Bonnie Tsai, etiquette expert and founder and director of Beyond Etiquette. “They may be experiencing some health issues that are causing them to feel more fatigued than usual or they may just appear that way all the time,” she says. “There’s no need for you to make them feel like they need to appear a certain way that’s acceptable for your standards or society’s standards.”

So, who are you voting for?
“Politics has always been a taboo subject for the dinner table and most social situations because it can alter the mood of a conversation very quickly,” Tsai says. “You can never be too sure of other people’s political affiliation and values and no one likes to be put on the spot by that question.” This is particularly important to remember these days when politics, religion, and other hot button issues are centre stage.

Why don’t you get out more?
You may see this as a gentle way to chide your friend into trying new things, hanging out, or even travelling more. “However, this question can be perceived as offensive because it sounds as if you are suggesting the person needs more exposure and knowledge and they are uninteresting,” she says. This may also be a sore subject if someone doesn’t have the same financial resources as you and wants to do more things but can’t afford to, she adds.

Oh, where is his dad?
This is one of these uncomfortable, painful and unnecessary questions that too often pop out in the moment, without thinking, Parker says. “This is an intensely personal question and if people would like to talk about their personal life they tell you,” she says. “Resist asking to satisfy your curiosity about their family situation.”

Are you a man or a woman?
We are living in a very different time than previous generations and gender and sexuality are frequent topics around us but while it’s fine to discuss it in the abstract, it’s not fine to pepper an individual about their identity, surgeries, treatments, or anything else gender-related, Parker says. “Asking someone about their gender or sexual orientation is rude, inconsiderate, and in some circumstances, derogatory,” she says.

How old are you?
This is the perennial “do not ask” question and it is still on the list for good reason, Parker says. “We all know people who do not feel comfortable answering this particular question and that’s all you really need to know about it,” she says. Why they’re not interested in discussing their age isn’t any of your business.

Why are you parking in the handicapped spot?
“Any kind of question related to any kind of disability should be nixed,” Parker says. It’s normal to be curious but many disabilities aren’t readily visible and your question may lead them to feel uncomfortable or defensive. You’re basically asking them to tell you details of their private health history. “Anything about physical appearance related to a disability or disabilities should be strictly avoided,” she says.

Are you pregnant?
There really isn’t a safe answer to this question, and that’s the problem, says Lisa Mirza Grotts, etiquette expert and founder of the Golden Rules Gal. She may be pregnant but if she wanted you to know she would tell you but more likely she’s not. “A lot of women carry weight in their midsection and pointing this out is insensitive and hurtful,” she says.

What religion are you?
Just like politics, religious or faith-based beliefs are very personal and oftentimes questions about religion are based on assumptions, like location, ethnicity, or appearance, Grotts says. “In conversation with another you might have an idea about someone’s religion but never press the subject unless they bring it up first or they are a good friend,” she says.