Some time ago my wife and I had dinner with a client and his wife. We ended up splitting the check, but I wondered if I should have picked up the check or whether he should have. Here is the background.
I have my own standing rule that if the client comes to my office, or my area, I pay. If I travel to the client's office, they should pay. This has worked well for me for ages. Usually the client offers to pay all the time, but if it is on my turf, I tell him that it's my turn since it's my turf. Never a problem. It also establishes that he or she pays when I go to their office, which is, by far, most of the time. When I had my Manhattan practice, I belonged to a lunch club and this was never an issue since my guests got menus without prices (and I received a monthly invoice).
Socially, if we went to a restaurant that was a client, I would pay. Otherwise, the client usually picked up the check. If I bought tickets to an event, then the client paid for dinner; if they got the tickets, then I would pick up the dinner check. This worked well and was never awkward.
The client I had dinner with was living in Florida, and we met for dinner during a visit there. This is a very good (and wealthy) client that I always went to meet at his office for lunch, and he always picked up the check. This time, while the dinner was more of a social visit, he was still a client, and I could not relax as I would with friends, and something would always come up about his business or investments. When the check came, I expected him to pick it up, but it sat there on the table. When it was time to pay, he said "let's split it" and that's what happened.
In retrospect I felt I should have picked up the check since he was my "customer." In the whole scheme of things this was not a significant expense, and the gesture might have scored points. However, we were on his turf. If I were to be in a similar situation in the future, I would pick up the check right away.
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