It depends on the situation, like that question would be natural to ask if you're meeting someone for the first time, but if you're at work talking to a coworker you don't know super well but have talked with before, it would be more natural to tie it in with something like "so what did you do on the weekend?"

But honestly, most people love talking about themselves, so I don't think it could go that wrong.

A good thing to have, and this takes practice, is self awareness in conversation. Like, if you ask something and the other person makes a confused face, you jump in and go "sorry, that might be a weird question", but you say it with a smile or a little laugh so that it doesn't seem like you're on edge.

I was a lot worse at conversations when I was younger, what helped me immensely was going on a solo backpacking trip where I stayed in hostels and had to have tons of conversations with strangers. Obviously that's not a thing right now, but I wonder if there's some way for you to practice having conversations with strangers? I know online is a lot different than real life conversations but there's a subreddit called /r/CasualConversation, maybe you could practice talking with people there?