If he asked you out, leave your wallet alone when the bill arrives. If he pauses as he is subtly hinting that you should contribute even though he asked you out don’t offer. If the check is still on the table 5 minutes after the waiter placed it on there and the clock is ticking away and he STILL hasn’t done anything about it, stare at him in the eyes, and ask should we get out of here? If that doesn’t prompt anything say in the sweetest voice dinner was lovely, thank you for inviting me. If he is not responding, girl he ain’t worth a second date and I wish I could be there to shake him silly like a rag doll!
If you invited him to a meal or any date where there is a transfer of money, you must reach for the wallet. Most guys will not accept you to pay, although in todays modern era and in the land of many self-righteous men, they will let you pay. So whatever. You asked, so deal with it, and do take pride in how nice it feels to contribute. Men on some level and at some point do really like a woman (regardless of her age or how much she makes at work) to contribute. I always think a cute thing is for him to grab the movie tickets but you insist on grabbing the popcorn and soda. Or he gets dinner but you buy the ice cream. Another one is he gets the groceries for your cooking date but you are hosting at your home with your favorite bottle of wine or your homemade chilled cookie dough waiting in the backdrop. It’s pretty much the little things that work and make someone feel appreciated and that you are reciprocating in a genuinely kind way.