Don’t openly inquire about menu or drink prices beforehand. Making money an issue will only draw concern and take away from the gesture.
Step2
If possible, try to arrange payment with your server before night's end. Use an excuse to draw him/her away from your companion and set up a tab with a credit or debit card.
Step3
Go to a familiar place. There'll be no surprises in terms of price, and a preexisting relationship with a server or bartender will make arranging for prepayment that much easier.
Step4
If a bill does arrive at the table, avoid the fight over paying it. Expect it beforehand, and have either cash or a credit card ready to slip into the bill jacket. Hand it back to the server immediately.
Step5
Be casual. This cannot be stressed enough. Treat the gesture as a habitual action, not a special favor. Never imply strings attached.
Step6
If your companion insists on paying part of it, negotiate. Tell them that you’ll pick up this tab, but they can get the next. This is especially effective for dating, as it subtly opens the door to the next get-together.