[Ashley V]

I'd just let him pay. He's a big boy and knows his finances, but I definitely see why you are concerned. If you feel really bad and want to do more than just cook him dinner every now and then, tell him you want to do _____ and prepay for it without telling him. When you go to whatever it is, and he goes to pay, then kind of flirtingly be like "Gotchya" and explain that you are treating him this time. I wouldn't make a huge deal out of it - actually, just appreciate it, because in today's society not many men are very chivalrous.