Don't be cheap, decide whose gonna pay before you go. If he's a gentleman your dining with, there's no question he'll pay.
Yes you can split the check
I've never had a problem throwing down a couple credit cards when the bill comes. Usually split equally though. I would maybe ask beforehand if you wanted totally separate checks.
As they said... let the server know because some places have a plate charge if you're sharing a meal.
Haven't ever tried but I don't see why they wouldn't let you.
I imagine you should be able to. It's probably best to let your server know right off the bat to be sure.
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