Jaya and I have a large group of friends that we regularly eat out with, so trust us that this advice works. However, this is the sort of thing that only works if everyone does it, so don’t be that guy and don’t accept repeat dinner invitations from people who don’t cooperate. If bad group dinner guests find themselves not being invited to things, hopefully they will figure out why.

• When you sit down, ask if it is possible to split checks. Some places are more accommodating than others (for some reason this is regional and I don’t really understand why.) In New York they tend to not want to do it.
• See what everyone is in the mood for. Is everyone hungry and wanting to split appetizers and desserts? Or is this more of a single entree per person crowd? This can help avoid the next point.
• Try to avoid situations where some people are ordering a small salad and water and some people are ordering 3 courses and tons of booze. This leads to the flow of the meal being different for everyone and extending it way out for the people ordering little. It also causes problems when it is time to split the check (if the waiter can’t do it per person and bless those who can!).
• Splitting the check evenly is fine! As long as everyone’s bill will be roughly the same anyway. If you have the salad and water vs three courses with wine, you MUST split it per person. It is wildly unfair to let someone subsidize your dinner. Make sure your share of the tax and tip is in proportion to your total bill too.
• There is an easy trick for making sure you are covering your fair portion of the tax and tip: take your total bill and calculate 30%. This is a little high, counting the tax at 10% (when in NYC it’s 8.875% and other places certainly less) but it’s MUCH easier mental math than figuring out the exact amount and that way you know you are covered and the waiter is getting a good tip.
• If it’s a birthday, split the birthday person’s share, if that’s amenable to your group. It’s a nice thing to do.
• Bring lots of cash (in a variety of bills if possible), it’s much easier to split that way.