QUESTION: Last night my husband and I went to dinner with two other couples. The women had decided that would be fun to do, but we did not discuss how to pay the bill. When the waiter brought it to the table, it became very embarrassing since we did not know if we should split the bill (some ate more than others) or if everyone should pay for exactly what they ate and drank. We ended up splitting it three ways, but how should we have handled it?
CALLIE'S ANSWER: It would have been easier to tell the waitress that everyone was going to be separate before you ordered. Since you didn't request this, the easiest way is to just split the bill. If someone offers to buy the whole dinner, you MUST reciprocate next dinner. It is rude to always let others get the bill. Dinner out is supposed to be a treat; fretting the little things ruins it.
LILLIE-BETH'S ANSWER: If you don't mention to the waiter ahead of time that the bills will be separate, it's easier, with less hassle, if all of you split the bill evenly, at the end. If you all know each other well and plan to do it again, the differences are minor and should eventually even out the more times you share meals.
However, if there's a big discrepancy in what everyone ordered (usually that happens when some order alcohol and others don't), it's easy to look at the bill, estimate what you owe and add extra for the tax and tip and to cover any small mathematical errors. You can always say something like, “I had wine, so I will pay for mine and add about $12 more for that,” or, if you were the one who didn't have alcohol, gracefully suggest, “why don't we split the food part of the bill and everyone pay for their own alcohol?” Whether you estimate or split a bill, try not to get too caught up in a penny-by-penny breakdown — it's more important to enjoy time with friends than to worry about a few dollars' difference in either column on a single occasion.