How do you honestly feel about being asked "how are you?" out of the blue in chat?

I have social anxiety and I tend to overthink what I do. There are these people in my life (family) that I need to be socially cordial with because they fund my studies and could potentially help me land my job after college. However, we're not that close although they are technically defined as my "immediate family". One of my relatives said that it helps to ask them how's it going every now and then. I just can't seem to think of that act as something genuine for some reason though. It seems weird to me to just ask them out of nowhere.

So I want to know if I'm just overthinking this or what. Because I really do want to be in good terms with them and I want to overcome this anxiety when it comes to social interactions and building relationships. I know things like this should be much easier now because of social media but I think my anxiety is clouding my mind so I can't think straight. I'd like to know your thoughts.