How to avoid sending "creepy questions": finding the right distance

Questions that put people off even when you mean no harm

"What did you do today?" "Where do you live?" "Do you have a boyfriend (or girlfriend)?" Even questions that are normal between friends can suddenly scare people when sent anonymously.

The reason is simple: when it's anonymous, the person "has no idea who's asking." When a friend asks "What did you do today?", it's a conversation. When a stranger asks "What did you do today?" anonymously, it feels like surveillance. The same words leave a different impression depending on whether they're anonymous.

Understanding this gap in how things feel is the first step to not being seen as creepy.

Patterns of questions you're better off avoiding

Pattern 1 is "questions that try to keep track of someone's activities." "Where are you right now?" "What time did you go to bed last night?" "What time do you usually get home?" Asked anonymously, these could come across as stalking.

Pattern 2 is "questions that dig into someone's appearance." "How tall are you?" "How much do you weigh?" "What are your three sizes (a Japanese term for bust, waist, and hip measurements)?" Some people dislike questions about their body even from people close to them. All the more so when it's anonymous.

Pattern 3 is "questions that probe someone's relationships." "What's your relationship with X?" "Do you like that person?" Questions that pry into someone's relationships tend to put the person answering in an awkward spot.

What they have in common is that they "go too far into the other person's private life." With anonymous questions, it's safest to ask within the range of what the other person has made public.

Persistence shows in "how often" too

Even if each question is normal on its own, sending them to the same person over and over can make the sheer number feel scary. Once they notice "It's this person again," they'll be on guard no matter what you ask.

Even when you're anonymous, people can sometimes tell it's the same person from your writing habits or timing. Hold back from sending several in a row in a short time, or sending one after another when they haven't answered.

Questions are something you send while respecting the other person's pace. Leave some space and be patient enough to wait for their reaction. That calm will likely help your questions feel safe to receive.

Even compliments get scary when they go too far

Complimenting people is a good thing, but going too far can backfire. Excessive praise of someone's looks in particular tends to feel creepy when it's anonymous.

"You're cute" is one thing, but words that keep praising details of their body or face may give them chills. You may mean it kindly, but the person receiving it might feel like they're being watched.

If you want to compliment someone, it's safest to aim at the parts they "choose to show," like what they post, how they think, or their taste. A light, casual line should come across more pleasantly than persistent praise.

If they're put off, back off gracefully

After you send a question, it's also important to pay close attention to how the other person reacts. If their answers get curt, or only your similar questions get ignored, that may be a sign that they want you to stop.

When you notice that sign, have the courage to back off gracefully. The more you push because you want more of a reaction, the more wary they tend to become.

Goodwill and interest only mean something when the other person can receive them comfortably. People who can back off when they should tend to earn trust in the end. The kindness of stepping back and reading the other person's mood creates a distance that never feels creepy.

Reread it as if you were the one receiving it

Before you send a question, there's one check we'd like you to try: imagine "How would I feel if I got this question from a stranger?"

Things that are hard to notice as the sender can suddenly become clear when you put yourself on the receiving end: "This is a little scary." If you flip your point of view, you can stop just short of sending a risky question.

Precisely because it's anonymous, the extra step of imagining how the other person feels is essential. If you use "Would I be happy to be asked this?" as your yardstick, you can probably cut down on questions that make people uncomfortable.

What makes a question keep a good distance

A good question is "one the other person can enjoy answering." The test is simple: imagine, "Would I be fine being asked this question out loud in a classroom?"

"What music do you like?": fine to be asked in a classroom. OK. "What are you into lately?": fine. OK. "Who do you usually walk home with?": I wouldn't want to be asked that out loud in a classroom. Not OK.

If you think with this test, your questions will move closer to an appropriate distance. When in doubt, choose not to dig deeper. Doing that keeps down the risk of being seen as "creepy."