Good question here, TBM.
To be honest, I just feel things out. Generally, if I invite her to something where she wasn't expecting to have to pay a significant amount of money (such as inviting her out to dinner), then I'll pay. But if we happen to just be having a night out on the town and decide to stop at a bar/club/restaurant, then I usually just pay for my own bill without mentioning it, and you'll often find that she'll just do the same since she wasn't actually expecting you to be spending money on her in the first place.
Once in awhile she may even offer to pay for you. Or, maybe she'll invite you out somewhere, and then she'll offer to pay since it was her idea. For me, the key element is determined when the invitation goes out: was the invitation to something where (a significant amount of) money was expected to be used (i.e. a romantic dinner?) or was the invitation for a walk on the beach where you ended up at a coffee shop or food place spontaneously? If it's the latter, then I usually only pay for my own part, and you'll often find that she won't be expecting more than that anyway.
If you've sold yourself as a "poor, traveling entrepreneur with big aspirations" (as I believe Chase does quite often), then you might be able to get away with having her pay for the majority of the outings. But if she knows you work a 9-5 job as an engineer or investment banker, then it'll be tough to expect her to pay for everything without her giving you lip about it.
Those are my thoughts.
- Franco
