Bad date hypothetical

Even if they ask for separate checks at the outset, if one person ditches, the other person/people is/are going to be responsible for paying. They're still part of the same party, so far as the restaurant's concerned. It's like a roommate scenario: You can have any private deal you want for distribution of the rent, but the landlord still needs to get paid, and "I paid you my half, my roommate is the one who flaked" isn't going to help you. You can go after the other person for compensation later, but you're still expected to pony up the cash.

Also, a little dating etiquette: Don't bring up separate checks when ordering, at least not if you were the one to ask for the date. There are a whole host of reasons that's a bad idea. General protocol says that the person who asked for the date at least offers to pay. Frequently, protocol also says that the other person will volunteer to split the bill when the check comes, and that's certainly fine, but you don't ask someone out, then obligate them to separate checks in advance. It makes you look cheap, and it has an undercurrent of "well, there's not going to be a second date, I'll just cut my losses." Even if it's true, it looks bad.

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