First off, I’m am not seeing really great communication skills coming from your end in your story here.

he keeps insinuating there is something wrong with me just because I don’t ask him about his private life

This is predicting. Or do you actually know he thinks this? The use of ‘insinuating’ sounds like you’re filling in a lot of blank space with your own narrative. Unless he came out and actually said this, private information isn’t necessarily an unspoken agreed upon trade. And if it was that would be a fault on his side.

And Just to get it out of the way: Introvert isn’t where you don’t want to socialize. It’s just a personality trait in how you recharge with or without socializing. Typical introvert would not avoid socializing altogether. They’d socialize and then excuse themselves for a time being. This is of course with healthy preferences of who to socialize with like any average person could have and that is perfectly fine but that isn’t a trait of what makes a person introvert or extrovert. That’s just having standards.

Either way, this just sounds like you have made a choice that this person isn’t for you and you have some unspoken boundaries and expect someone to know your boundaries without telling them. Even if you think you are being clear with social queues this might be a case of miscommunication of what a social queue is for you and what he reads communication(possible) . But I wouldn’t leave that to assumption.

People aren’t mind readers so of it is bothering you this much you could tell him like several others are suggesting.

after that if he doesn’t let up, see HR as that would be harassment at that point.

Tell him straight up. Unfortunately the only approach is direct or it will get worse. After you tell him, tell your boss the conversation in case the coworker tries to be petty and report you.

I am a manager at my job and see this type of stuff all the time. Could it be he simply wants to be friendly? Sure. Either way it’s better to be direct so there is zero confusion.

I would tell him, “Look John, you’re a nice guy but I’m not interested in making small talk with you”. And then just continue your work. If he doesn’t leave you alone after that then it’s time to go to HR. Please do not feel bad. Some people lack self awareness at the workplace and don’t know how to act in a professional setting.

Most of what I’m seeing here sounds too confrontational or passive aggressive to me. What I would do personally is wait until he asks you if everything is okay again and then say something like this:

“Yeah, all good here. So you know, I’m not quiet because something is wrong in my life or between us, I’m just very introverted and my natural state of being is not to open up”

Most people tend to assume other people’s internal state is works similarly to their own, unless it’s an aspect where they know they are far removed from the norm, so for an extrovert, they equate you being quiet to what would cause them to be quiet. Without telling him the reason you act differently, he will continue to assume this.

By wording it as an FYI, you give the opportunity for him to understand the difference and change his behavior without telling him he has been doing something wrong, because best as he knows he hasn’t been, and so you hopefully prevent him from getting defensive.

If he continues, then maybe you can go to a more confrontational approach. That’s how I would handle, at least.

I am also a woman and I’m guessing you are not from your username, so ymmv with communication like this.

Tell him you feel shy around him because you're attracted to him, and then ask him out on a date. Either he'll leave you alone or you'll get some. Win/win

This website completely changed the way I thought about this stuff and I found it super helpful.

The line to walk, generally speaking, is, "When you do [specific behavior], it makes me feel [specific emotion]." So for example, "When you ask me if everything's ok, it makes me feel pressured/put on the spot."

Keeping it about your own feelings makes it less confrontational while still bringing attention to the problem - you don't wanna get drawn into a whole debate about whether there's anything wrong with asking if someone's ok, but you want him to understand how you feel and (hopefully) take that into account in the future. If he does get defensive, repeat the message once to make it clear you're standing your ground, but then drop it and move on. A lot of times it's just a matter of the other person not realizing how it affects you.

Having said that, speaking as someone who's very much had the same mentality in the past, there are a lot of advantages to having friends in the workplace. Something to understand about this approach is that it's actually good for building relationships because it allows you to confront the behaviors that bother you while openly communicating your feelings, and people may even respect you more for standing up for yourself. Just remember to walk a middle ground, you don't want to veer into aggression or passivity.

It's hard to refuse someone who on the surface is just being friendly, and who might take your rejection as a harsh assault on their fragile personality.

I think just try to communicate to him that he's distracting you from work. He might not actually realise.

If he can't be reasoned with, then maybe yes go to HR

"I'm sure you're perfectly nice as a friend, but I'm not looking for a friend. I like to keep my work and private life separate, and I'll thank you to do the same around me. Don't think I dislike you; but for me, personal chat is an unwelcome distraction."

"Please stop asking me if everything's OK. Everything is fine and your concern is appreciated, but I prefer to work in silence and I'm not getting any right now."

Something like "I don't like to chat at work".

The other suggestions seem far too inviting for follow-up or could be perceived as sidelong attacks.

That phrasing is hard to follow-up on, though not impossible, and focuses only on you. I suspect you also don't chat with others, so they probably can't say something like "But you chat with Johnny?"

Talking about what they're doing that annoys you opens a conversation about them feeling attacked or maybe trying to find alternate ways to talk to you etc. You don't need to explain why you don't want to chat because that will open other conversations. They probably will try to follow up or redirect, but calmly insisting that you prefer not to chat may work.

HR is generally a bad place for employees to take issues since their stated job is to protect the company from liability their employees might incur. If you have a union or some other third party resource go to them first, then go to HR if they advise it. Since HR is interested in protecting the company from liability created by employees you may be able to aim them at the other employee, but you need to be sure that's what they'll do before going to them, otherwise they may view you as the liability.

EDIT: And you don't need to wait for them to ask if you're OK. If your issue is that they're talking about non-work and that's not why you're there, just bring that up immediately.

And also be clear they can still talk to you as long as it's work related, and that you're not refusing to work with them. Otherwise you become an HR problem.

"I'm not interested. Please leave me alone."

You didn't tell us when he asks if everything is OK. That is a large omission, and I hope you can update the original post with examples of what led up to the question being asked. Also, what is the setup there? Are you working at Subway making sandwiches? Do you have adjacent desks? Do you show up to work with black eyes? We are left wondering what's up.

Certainly anyone who repeatedly asks "Are you OK?" is exacerbating some issue, but I would be hesitant to offer any advice about what you ought to do without reading more details.

(In other words, the missing missing reasons applies here just as it did in the original scenario, for those who remember it.)

going to HR over this seems ridiculous...

do this anyways.

they're creating drama for themselves and it will suck in more people if they don't get the validation they're seeking. either figure out how to give them what they want in a way that works for you (this usually doesn't work) or do everything in your power to protect yourself.

warning: if management sees them as more valuable than you are; you can expect going to hr to backfire.

"Look man, I appreciate the concern, but really, I'm fine. I just prefer not to socialize." Then divert your attention to something else.

Or you could pull an SGDQ and go with the ol' "I would really prefer it if you would be quiet."

Tell him the truth. He's so annoying you asked a bunch of randos on the internet what to do about hi.

Without knowing more about the situation, the best response is impossible to determine.

Are they fixated on you because they think you have social needs?

Has everybody else told them off because he is annoying and by not telling him off you are granting some degree of (passive) acceptance that he is needing?

Is he romantically interested in you?

"Look man, I just have no interest in having work friends. I am here to do my job and go home. You are distracting me from doing my job and I don't appreciate that." Or whatever.

Going to HR may be the smart move to avoid him going to HR about you not being friendly or a team player or whatever nonsense if you professionally tell him off. I wouldn't tell HR you are being harassed, just tell them that he is distracting you from work and don't appreciate it. If he continues after HR talks with him, then tell HR you feel harassed.

You going to HR can also take place of talking to him yourself. You talk to HR and ask them to tell him to let you work, they talk to him so you don't have to try and navigate his bullshit and you get the issue noted to support your side of things.

"Everything is good, thanks. Staying busy with work..." and then either get back to work or stare at them until it gets awkward. Its possible they have trouble with social cues and you seem friendly or nice or whatever, people are weird and being a new employee is stressful so trying to latch onto someone who comes across well can be a thing that happens. I try to redirect people like this to the topic of work and answer any personal question with something boring. What did you do this weekend? Laundry. If they have any self awareness they will eventually only talk to you about work. Stay professional and don't be rude while making it clear you are at work to do work and have no interest in their personal life or sharing any details of yours.

going to HR over this seems ridiculous

It's not.

More to the point, you should do so before he beats you to it, complaining that you're not being a "team player" or something.

it's gonna depend on the size of your work place really. hr isnt so much the group that is a resource for you the human. think of them like the IT dept that manages the human resource. if you've plainly stated your boundry to that person. "it's not your business what my mood is, if your uncomfortable with me not behaving in the excited mannor you want. that is a you problem". it's on your manager to ensure the other person respects that boundry. and if your manger doesnt do that, hr should definitely care because thats a problem. that said. it's far easier for everyone to just say "smile more, we're a family and we all behave the same way" in smaller org. and you'll have to decide if staying in a place that wont respect you boundries is healthy. my work pays me to complete specific things, not fill in someone's social circle because they need a trapped audiance to maintain friendships. i was lucky in my current org to have a manger who caught a situation like you describe happening to me and take zero nonsense from the other person. and now that i've worked with that expectation, with someone who would enforce that, i'm not willing to consider my persoanl life part of what the org is paying for.

Are headphones a possibility in your workplace?

You do sound rather aggresive. :) We introverts can be friendly as well. He is probably just insecure about the situation.

Become their best friend. Setup a hang out outside of work in the worst part of town. Don't show up. Make excuses. Do it again next week. Do it again until they hate you.

Just kidding. Set boundaries and pray the respect them. If they don't buy a valve stem key for tires. Barely loosen the stem so that it takes 3-4 days for their tires get flat. Repeat until they lose their job.

Just kidding. Stay in the basement, get fired for missing work, become homeless, get a job somewhere else.

There we go... juuuuust right.

Have you tried saying, "Please don't ask me that anymore"?

That will address the exact problem without being rude, without offending him, and without opening it up for more questions. You don't owe him an explanation, so don't leave an opening for one. Just say: "Please don't ask me that anymore."

If he asks why, you say, "Doesn't matter. Please don't ask me that anymore."

If he offers an explanation for why he's asking you that, you say, "Ok. Please don't ask me that anymore."

Neat and easy. No unintended consequences.

My coworker put up a sign that says, "I don't have time to chat."

"Really, dude? I am so tired of you asking that. It's none of your business if I'm ok or not. Stop asking."

Tell him directly first. Then if he persists go to your boss or HR and tell them you think probably he is trying to be nice but keeps interrupting your work and won't stop, and the distractions are starting to interfere with your work.

I have a similar coworker, was constantly coming by and trying to start up conversation. Asking what I did the weekend etc. Why I don't like their pears etc.

Finally one Monday morning when they came by wasting time I pulled off the headphones and asked "do you have a work related issue you need help with? " their response was "no I'm just socializing" I responded with something implying they'd actually be good at their job if they did that instead, and I'm not now or ever interested in socialising with them. They finally buggered off.

I'd always suggest being direct instead of waiting for other people to take a hint. Tactfully, mind you. Phrase it in a relaxed, emotionally neutral way that doesn't single him out. Something like "Really, I am doing fine. When I'm at work, I just prefer to focus on the work itself instead of talking with people. I'm more at ease that way."

That being said, is this the kind of work situation where you're one of many options to make friends with or is it more of a you and him stuck in a room together all day type of thing? He sounds like a lonely person and if the two of you are stuck together then the best idea might be to seek a social compromise between you two's preferences, like designating some specific portions of the day as times when it's appropriate to have a conversation. You try to be sociable for him when it's on, he tries to be quiet for you when it's off.

I would go to HR since this sounds like covert harassment to me. Don't think it's ridiculous - you have the right to be left in peace. Lots of red flags on your post. However, it's worth trying to talk to him first, so here are my suggestions:

If you are working: sorry Mr Loy, this is not a good moment. I'm trying to get work done

If you are not working, but also not ballsy enough to tell him to go away: sorry, I need to go ( go to the toilet or just pretend to be in a rush)

If you really want to set up boundaries anytime (recommended): thanks Mr Loy but I'm not interested

The tone in which you say things has a lot of weight though. If you can sound tired and bored of him, all the better. People who pick and harrass others typically go after people who react either hysterically or annoyed, or also after people who appear coy or shy and polite. I hope this helps.

"Fuck off"