I'd say it's better for everyone, including the restaurant servers, to discuss bill splitting before people start ordering things. Based on what /u/MrGuard1 said in the OP and in some follow up posts, he had a history of eating out at expensive restaurants partially or mostly at his expense with previous girlfriends and he was fine with that, but in this case he was annoyed that the woman he was seeing stretching his budget by ordering lots of pricey drinks, and that this had happened more than once.

Given that it would have been reasonable to say something like "I'll pay for the meal, how about you pay for the drinks?" before any food or drinks are ordered, followed by asking the server to bring out the meal check and the bar check separately right from the beginning. That way each person is treating each other to something and the experience is less tacky than haggling over the exact price of the bill after the fact.