The context of the following conversation is Ash put money in Quinn's pocket when he refused to let her pay for the dinner.:
Ash says i snuck money in Quinn's pocket when she wasn't looking.
The friend responds Quinn is so nice I don't think she ever let someone even attempt to pay for dinner.
Ash responds i just feel bad for her because she thinks she always has to pay for everything.
The friend responds she is really rich so I don't think she cares that m much about money though.
Ash responds you're probably right I guess.