Adapted from a recent online discussion.

Question: People in your columns often cannot believe how rude and intrusive someone's questions are. I am one of the people who asks these questions. I don't mean to be rude. I am just very open and direct, and asking questions is how I show my interest in someone.

The trouble is that what one person finds off-putting, many will find a great way to move past shallow filler conversation. I value this part of my personality, as it has enabled me to quickly make friends and get to know people at a deeper level.

I don't, however, want to make others uncomfortable. Is there something I can say to let people know they are free to tell me if something is too personal? Should I just accept that I will occasionally rub someone the wrong way?

Answer: "(Nosy question)? If that's too personal, then you can tell me to stuff it."

People do have different privacy thresholds, so I won't suggest you develop a whole new restrained personality, but it would be an act of kindness either to avoid the handful of hot topics people keep writing to me about, or to flag them upfront - as in, "This is a taboo topic so shut me down as needed," followed by your question.

I wonder if it's possible to come up with a universal Don't Ask List. I'll start: "Are you pregnant?"

  Comments: "When are you going to have kids?" or "Why don't you have kids?"

"What's wrong with your kid?"  

"What happened to your face?" 

Answer: Thanks. Just reading these is painful.

Comment: "You're so great! Why don't you have a boyfriend?" This is sometimes meant as a compliment, but I always hear it as "I can't tell what's wrong with you by just looking at you. Please explain to me why no one loves you." I have never, ever, ever gotten this question from a single person.

Also, I think the writer paints a false dichotomy between boring social niceties and "move(s) past shallow filler conversation." Lots of people use the "I'm not rude/mean, I'm just honest" dodge, and usually those people are jerks.

Answer: Fair enough, but it is true that some people can get away with bolder questions than others - and often it's because they convey genuine interest versus a lust for dirt. As in, non-jerks.

Comment: You are not entitled to have the world solve your boredom problem. You are not entitled to put people on the spot just so you can avoid what is (to you) deadly tedium. You are not entitled to know anything about anyone.

Answer: Yes, yes, you're right - but the initial question was about actually getting to know people, not about titillation. Being shamed into asking about nothing besides the weather is a lonely business.

The trick of drawing someone out versus prying is in not judging, isn't it? Wanting to know people, caring about them, goes over better than wanting to feel superior to them, and often it's not the question itself but the context that tells the difference, including tone, expression, and attentiveness to the answer.

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