I realize that was a super long post so maybe I should just ask:

If someone calls you everyday and asks you out to eat daily because they don't like eating alone (and they have the $ to eat out all the time, I don't) and you know they have a history of having a "daily" person (someone not involved in other areas of their life, I know of two others he"s had) am I a jerk to keep the "friendship" going if I seriously question whether I even like this person generally and find a lot of their behavior off putting/annoying because I'm concernd my mental health will be worse without the contact?