It was late and the restaurant was emptying out, the woman's party of twelve just finishing up. Since they were my last table of the evening, I was feeling relaxed.
"We have some members of our group who would like to pay individually," she said. "I can help you figure out who is with who."
"So you want separate checks?" I clarified.
She looked at me like I'd said a dirty word. "Checks? I guess that's how you call it. We have people who would like to pay for their own items."
I never figured I'd ever see anyone get touchy-feely over being referred to as a "check" vs. a person. I wondered if I should take the woman back to our computer terminal and introduce her: Computer, this guest would like to be recognized by her name, and not as check #432, got that?
Instead I blinked and got to the more pressing matter at hand. "We can do separate checks here, but typically we ask that groups make this request in advance. If we know beforehand we can keep track of everything, otherwise it gets complicated."
"I can help you..." she offered.
"It's OK I still have my map." I actually had the table mostly memorized since it was one of my last, but I wanted her to see my map with my god-awful handwriting. "Alright, who is together?"
She pointed out each person who would get a check, and who they were paying for. I made some more chicken scratches on my map to indicate this, then nodded and walked away, leaving her to cross her fingers as to the outcome of this exercise.
I handed them six bills, which had each beverage, appetizer, salad, main and dessert perfectly accounted for. As this took a while, I didn't want to keep them waiting even longer by adding gratuity to each bill. Also, when couples pay separately they usually tip better (since they aren't subsidizing Uncle Bob's 30 dollar steak or whatever the case may be;) for this reason, I personally don't mind doing individual checks.
I'd forgotten one thing however, which my boss pointed out when I came back with five credit cards and a cash payment: most of them were from out of town. Four of the six "checks" tipped 10%.
Of the necessary transactions that take place in a restaurant day to day, it's almost always the tip line on a credit card slip that dehumanizes the most.