I've taken people (groups, my team etc) out to eat many many many times... just so you know, the person you are describing self limits through all this stuff. It NEVER bothered me to see it and pay for it. Not Once... The lack of self awareness, the lack of being able to see themselves in space and understand the impact of his actions... the end up limited in their careers... I'd always prefer to be the person stuck with the bill and the one responsible than hoping for a free lunch... NEVER take a free lunch because, you know, it ain't free mang.