Asklemmy

This website completely changed the way I thought about this stuff and I found it super helpful.

The line to walk, generally speaking, is, "When you do [specific behavior], it makes me feel [specific emotion]." So for example, "When you ask me if everything's ok, it makes me feel pressured/put on the spot."

Keeping it about your own feelings makes it less confrontational while still bringing attention to the problem - you don't wanna get drawn into a whole debate about whether there's anything wrong with asking if someone's ok, but you want him to understand how you feel and (hopefully) take that into account in the future. If he does get defensive, repeat the message once to make it clear you're standing your ground, but then drop it and move on. A lot of times it's just a matter of the other person not realizing how it affects you.

Having said that, speaking as someone who's very much had the same mentality in the past, there are a lot of advantages to having friends in the workplace. Something to understand about this approach is that it's actually good for building relationships because it allows you to confront the behaviors that bother you while openly communicating your feelings, and people may even respect you more for standing up for yourself. Just remember to walk a middle ground, you don't want to veer into aggression or passivity.