When the check comes at a restaurant, who pays? As you can imagine, that depends highly on the circumstances. Our correspondents, Peter Bonventre and John Jannuzzi, tell all.

Peter Bonventre

To split or not to split? A conundrum that once rarely concerned me, as I spent a good chunk of my career at big media companies that blessed their writers and editors with generous expense accounts. Seems like a dream to me now. But, hell, I’ve been around the block a few times, and along the way, I’ve learned some things I’d like to share.

When the waiter drops the check on the table, three possibilities hang in the air: You pay, someone else pays, or you split the check with your table companion(s). Okay, let’s break it down. For one thing: If you’re dining with the boss at a business lunch or dinner, he or she pays. For another: If you invited your table companion(s) to dine and feel obligated to pay, then you call for the check when the meal is done, and you whip out the cash or the credit card before anyone can blink. If someone starts to challenge your right to pay, you firmly tell that person there’s always a next time. Never argue over a check. Oh, and guys, call me an old-school fool, but when you ask a woman to dinner, you pay. When you ask her out a second time, you pay again. And so on. Don’t worry about offending her feminist sensibilities. You won’t. If you think feminism is about who picks up the check, you’ve got a lot to learn.

Now let’s talk about splitting the check. For any number of reasons—the exorbitant cost of dining at a fine restaurant, the frequency of dining with the same circle of friends—it’s an ideal formula for an evening well-spent without the looming threat of bankruptcy. In many cases, it won’t matter who invited whom to dinner or who signaled the waiter for the check. When the check arrives, suggest splitting it as you plunk down your credit card. You might be surprised at how readily all will agree, and you’ll quickly establish a pattern for future dinners. Just remember: Whether you’re splitting the check in half with another couple, or four ways with three pals, split it evenly. Don’t itemize. And each of you should leave the same 15%-20% tip.

Finally, I shouldn’t have to tell you that you must never, ever ask for separate checks. Right?

John Jannuzzi

At the end of every meal in a restaurant, the bill is bound to come. And no matter how much you’ve been enjoying yourself, the check can dampen the mood. Not because you’ve run up a tab, but because there can be awkwardness in splitting a bill. Do you go even? Does one person take it all? Do you divide the check by what was ordered? Did one straggler only drop by for a whiskey? So many damn questions. So many damn possibilities. Below, some advice:

If you’re on a date, and you are the proactive party, you better be prepared to pick up the check – in full. If you’re not interested in going out with that person again, you should still pay. Asking another person to split a check in a restaurant that you chose on a date that you requested? Bush league move.

Business outings are another story. For these situations, I always consider exactly who I’m with. My boss would take me out to lunch every now and then when I was young and poor. She being older, more moneyed and superior, always paid. As the boss, it’s not good policy to ask your subordinates to pay if you’re taking the team out. And if you’re in the position where you can expense the meal, always pay. (Unless you’re content with being a dick.)

Now, to dinner with friends. My god, what a headache it can be. After a certain age, when you and your peers are all working and supporting yourselves, an even split is the way to go. In 2014, the sight of each diner tossing their respective credit card(s) and cash into the center of the table is familiar  to us all. You’re going to end up eating some money some of the time, but on other occasions your amigos will be the ones getting the raw deal. Ultimately, you’re paying for the time spent with your friends, not your pork chop and their striped bass. And the fellow who had only one drink? Offer to buy him another one at the bar down the street.

It all balances out in the end, trust me.