Asklemmy

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

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.

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

"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.

"What's wrong?"

"You keep pestering me when I want some quiet time."

You've got to be realistic about things.

"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."

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

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.

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

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.

"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.

"Fuck off"