Is it ever okay at a restaurant to assume your dinner is going to be paid for by the other party?

Of course. But these situations have to be approached strategically. For instance:
- Never say, “I insist” one too many times. You’ll might win.
- Make sure you don’t reach for the bill when the presumed paying party isn’t looking. And, if this happens, PLEASE do not try and put it back.
- NEVER smile and say, “You didn’t have to do that!” UNTIL you are 100% sure the presumed paying party has in fact paid the bill.
Here’s a successful scenario I was in a while back when Tyler’s parents, Bill and Nancy, took us out to dinner.
Walking into Cheescake Factory:
Me: I’m pretty sure Bill is going to pay for our Dinner.
David: Yeah, but there’s that certain amount of resistance we have to give.
Me: True, and I think I’ll blog about it on Monday.
Finishing up at Cheesecake Factory
Me: I’m so sorry I have to eat and run, but I have a flight to catch.
Bill: We totally understand.
Me: Can I just leave you money for mine?
(I had zero cash in my wallet. This was risky.)
Bill: No, I’ve got yours.
Me: Are you sure? I can pay.
(No I couldn’t)
Bill: Get out of here. I’m paying.
Me: (with a dash of surprise) Gosh, thanks so much.
Bill, I know you’re reading this. I’m sorry for pretending I didn’t know you were going to pay. Next time you really don’t have to (wink).






10/24/2011
Seriously