I've got a friend who's quite a bit younger than me and just finishing Uni. Over the last couple of years, whenever we've gone out, I've tended to buy her drinks, as she's not got much money. (To be clear here, she's the girlfriend of a friend of mine so it isn't a 'date' scenario).
I've never particularly minded doing this but I'm now potentially going to be jobless and working freelance whereas she's finished Uni and, at some point, will presumably start working so I think it's time I gently moved away from buying her drinks all the time but I'm trying to work out how to do it in a way where I don't make her feel guilty or awkward about the fact I've tended to buy her drinks in the past or create any ill-feeling.
Let's assume for the sake of argument I've sent her a link to this thread already.