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.

'None of your business, motherfucker."

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.

I think a direct approach is best and not caring if the person gets offended but also not trying to offend them. Something like "Sorry i don't feel comfortable with you asking about my personal life can we keep the conversation professional?"

Then if they dont accept that, and keep at it is when youd go to HR.

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

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"