Chipping In....Or Splitting the Bill

It's very awkward when, say, family members decide to chip in and get a gift for someone together. For instance, I have a brother who's married and a sister who's married. For Mother's Day, we've considered all chipping in to get our Mother a more expensive gift that she really wants. Only problem is, how do you split it? Most would say three ways. However, there are really five of us chipping in, so shouldn't the gift be split five ways? Otherwise, I'm paying as much as two couples with two salaries coming in. It's a delicate matter, and who wants to argue over a Mom's Day gift, when it's something Mom really wants? And then there's the after-work dinner with the co-workers or girlfriends.You all go to a restaurant. One orders the cheapest thing on the menu and a glass of water 'cause she's broke. But another one orders everything from the Margarita to the appetizer to the lobster dish to dessert. And then the bill comes and somehow gets split evenly. Or, the person who should leave the biggest part of the tip throws a dollar down on the table. And the person doing the bill calculations is somehow always left paying more. It's enough to make you want to stay home with a good bowl of mac and cheese!