My guy friend and I have been very VERY flirty recently and have been vibing on so many levels of depth. (We both have the same health problems and have known each other for a really long time) I’ve started catching feelings and want to ask him out, but from being friends I know he’s not into being in relationships anymore from previous bad experiences. I don’t want to ruin our friendship if it goes poorly, but I would like to be more than friends. Should I go for it or not?? Any advice??