Who Pays & When?

Don’t fall into the offer to pay trap. A good woman will offer to pay or possibly go Dutch on the check. Don’t let her under any circumstances. She’ll talk it over with her friends and they’ll decide you are cheap. You’ll never get any love.
After you’ve been sleeping with her on a regular basis you can start letting her pay. A good benchmark is to compare salaries, you might not know hers, but you can guess).
If she makes half of what you do, then you should probably play the sugar daddy role and suck it up most of the time.