Just get the lay of the land.   If the land is full of lardasses with a lardass principal that BBQs with the target lardass, that might not be a good idea. Stop trying to lawyer personal interactions.  Stick to reality.  Straight up pure popularity, do they like your friend  or the lardass.    If they hate the lardass then go for it.  But check the water and don't rely on "rules".