Comment by mewpmewp2

Yeah if an awkward person does it they can be called out as if they are interrogating or interviewing. I actually remember trying these tactics when I was teenager... and that is how it came off. I tried so many weird things because I was so unhappy with my social performance.

Usually safer way is making observations rather than directly asking or at least continously asking things over and over as if to desperately try to keep the conversation going.

But even then if you are awkward, it will still come off awkward and people will try to excuse them out of that situation no matter how much theory you might read online.