Asklemmy

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 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.

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

"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 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"