Most Helpful Girl
I am very aware of the fact that at my age, I tend to be more financially secure than men significantly younger than I. I would feel the guy would find it insulting if I insisted on paying for everything all the time, but I do insist on going half or the tried and true "my turn, your turn."
Most likely your older woman is just feeling sympathetic to the financial situation of younger folks. I can see where it would make you feel odd, though.
Next time you are out, grab the bill first before she does and tell her "It's my turn.". Or, offer " OK, you got dinner but the movie is on me.".