Asking the same person many times? Small question box worries answered

It's fine to send as many as you like

To get straight to the point: it's totally okay to ask the same person questions as many times as you want. In fact, quite a few people create question boxes because they'd be happy to get lots of questions.

Think about it. People create question boxes because they want questions. Some people even feel lonely when no questions come in. Your sending questions should be something that makes the other person happy.

Worrying "Am I being pushy?" shows that you're considerate, but you don't need to worry that much. Even when it's anonymous, some clues remain that the questions come from the same person, but your name won't be shown.

That said, a few things to keep in mind

It's okay to send as many as you like, but there are a few things to keep in mind.

First, don't send the same question over and over. Sending "What's your favorite food?" 3 times will get you the same answer. Send different questions.

Second, wait for an answer. If you send a question, then another one 5 minutes later, then another 10 minutes later, the other person's inbox fills up with questions from the same person. A good pace is to send the next one after your previous question has been answered.

Third, watch how the other person reacts. If they say something like "That might be a few too many questions" in an answer, slow down a little. As long as they haven't said anything like that, you don't need to worry too much.

"Am I bothering them?" is usually overthinking

Worrying "Am I bothering them by sending so many?" shows that you're considerate. But that worry may just be you overthinking it.

People who open a question box want questions to come in. Few people would feel that the questions they receive are a "bother." In fact, some people are happy to get a reaction.

People tend to imagine the worst about how others see what they do. But the other person may be less bothered than you'd expect. Rather than holding back out of worry, why not go ahead and send one?

Being noticed as a regular leaves a good impression

If you send questions often, the person answering may notice from things like your writing habits that "this might be the usual person." But there's no need to be afraid of that.

To the person answering, someone who keeps sending questions is someone to be grateful for. They may even take it warmly: "It's this person again, how nice."

It's just like a regular customer being remembered by the staff at a shop. Becoming a familiar face isn't a bad thing. Instead of shrinking back and worrying about being noticed, enjoy asking questions with confidence. Being a regular doesn't necessarily mean you'll be disliked.

Send at a rhythm that's fun for you

It's fine to send as many as you like, but if it starts to feel like a duty, that defeats the purpose. It's fine to send questions when you feel "I want to ask" or "I want to chat."

There's no need to pressure yourself with "I have to send one every day." Ask what you want to ask when you feel like it. Keeping it that light makes it easier to keep going.

Send not for the other person or for anyone else, but because it's fun for you. Value that rhythm. Getting involved at a pace that doesn't strain you will likely make the exchanges naturally more enjoyable, too.

Send your support as many times as you like

Not just questions, but also messages like "I always watch your posts" or "I'm rooting for you" can be sent as many times as you like. In fact, support that keeps coming should help hold the other person up.

Even when people have been told something once, they may forget it as time passes or lose confidence. That's exactly why words like "I love what you do" or "Do your best" that arrive every so often may feel just as welcome every time.

There's no need to hold back because "I already said it before." Even if the feeling is the same, it's worth something every time you share it. Your repeated support might give the other person the strength to keep posting.

Regulars are a question box's treasure

For people who run a question box, regulars who send questions again and again are people to be grateful for.

When someone asks from a different angle each time, the variety of answers grows and the question box tends to get livelier. Writing answers while thinking "Another fun question came in!" is an enjoyable time for the person running it.

So don't hold back, and keep the questions coming. Your questions should help make the other person's question box a fun place.