It is such a great pleasure to dine out with friends, to share good food, wine and conversation. For example, I recently had a fantastic evening at Myers + Chang, after the Boston Wine Expo, with friends, some old and some new. We devoured plenty of delicious food, drank some interesting Saké, talked about a variety of topics, laughed, and just had fun. The entire experience was perfect.
But other times your evening, which had been proceeding so well, can fall apart at the end when the check comes, when it is time for everyone to contribute some money. I think we all have been to dinner with very cheap, if not miserly, dinner companions. They might grab their calculator and try to break down their share of check to the very penny. Or they might try to offer less money that what they actually ate and drank. Or they fail to add in taxes and gratuity into their contribution, shortchanging everyone. In the end, the other dining companions often end up paying more than their fair share, making up for the difference due to the cheap ones. That just ruins the night.
I am not sure those cheap people will ever change. It seems ingrained in their personalities. One solution is just not to go out to dinner with those people again. And that does happen. You could also make a division on how to split the bill prior to going to dinner, maybe agreeing to an equal split. You can also just live with it, as part and parcel of the cost of being friends with such people.
When I dine out with friends, I prefer to just split the check equally, especially if they are friends with which I go out frequently. Any individual inequalities for a particular dinner usually get worked out over time. It is certainly the easiest way to handle the check. It is also more equitable if everyone is sharing dishes and drinks.
It can be fine as well if the check is roughly split based on what people ate and drank, though you need people willing to consider all relevant factors, including tax and tip. And they can't be worrying over pennies. You know you have a group of good people when the amount of money you gather is actually more than what is owed. It indicates people are overestimating, which is better than underestimating. You can always give people back some cash.
How do you handle the check when you go out with friends? How do you handle cheap dining companions?