I know several women who spend more than they feel comfortable affording because the guy they are dating picks expensive restaurants and activities, but it is assumed everyone is still going dutch. Sometimes even if they eventually say they can’t afford it, the guy seems to not pay attention. But, more often the woman says nothing, and complains behind his back to other friends. I have no idea if men do something similar? If they are afraid to say things are getting too expensive?
In my opinion, and this is from someone who has not dated in a while, the time to discuss finances regarding how much is spent on dates and activities is whenever it is applicable. Don’t go on a bunch of dates you can’t afford, it shows financial irreponsibility.
As far as talking about how much income you actually make, and debt you might have, the real details of your financial situation, probably as you are becoming exclusive with each other, and considering living together or marriage is a possibility in the future, feeling like you don’t see breaking up any time soon, then eventually money will come up when planning vacations, or a new job offer or promotion, considering moving to a new house, paying a bill, and the conversation will just happen.