Hell, if someone ALWAYS offers to pay, I let them do so.
I'm rather used to being relatively poor, and I figure whatever.
Probably sound a lot like your quasi-friend. On the other hand,
my friends (when I had them) would never make such foolish
offers, unless I mentioned that I didn't have enough money to
do something - in which case they might (usually just loans though);
I'd do the same for them too.