First date he paid, I gave the tip, Do I tell him I will pay this time or at least try and tell him I will pay, or let him pay?
Most Helpful Guy
I think you should offer. It sends him a really good sign, which is that you're an independent woman but more importantly that you actually enjoy spending time with him even if it costs you money.
Most likely, he will pay. But he'll feel even better about paying, knowing that you don't take it for granted.2