Frum_Bachur,
I’m sure that you ate meals at those restaurants and watched the movie and ballgame yourself, so around half of those costs you listed were for your own entertainment.
Nobody is stopping you from asking the young woman to help defray the costs of the dates. If you choose to do that, however, it might be a good idea to let her know in advance so that she can prepare. Also, allow her to choose some of the venues, because you don’t want her to feel pressured to pay above her means. That said, I don’t think it’s a good idea, becuase it may lessen your chances of making a shidduch, which is the whole point of dating in the first place. You did, after all, write, “you get what you pay for” 🙂
Another option is to choose less expensive venues.