You are both being disingenuous. You should scale back your lifestyle and stop living so high on the hog, so that you definitely aren't pressuring her, and she should be regularly contributing something towards your dates. It's madness, if she's broke to expect her to pay $100 towards something, but not crazy to expect her to buy the next round of drinks, or a pizza, or the occasional dinner. If she shows signs that she is losing interest when the pressure's off, but so are the expensive treats, then you'll have your answer. If she foots a modest bill when your social lives are less hectic, then you'll know she's sincere.