Carolyn Hax: Brother-in-law takes advantage of others’ generosity

Dear Carolyn: My very generous and wealthy (this is relevant) friends offered to throw a dinner for me and my husband for our 10th wedding anniversary. This is a second marriage for both of us so we’re all in our 50s. They asked for the guest list and we gave it to them, including my brother-in-law.

He’s the sweetest guy in the world, would do anything for you, but does have this flaw that he’s always looking to “make out” or game the system, if you know what I mean. He ended up ordering pre-dinner drinks that had to total in the hundreds (three shots of a very expensive scotch), he ordered two steaks for dinner and no sides, and he chose a bottle of wine that my friend who sat next to him later told me ran five figures.

Our friends didn’t balk at the check but you could tell they were surprised at the final total since they discreetly asked the waiter to confirm the charges. I would like to address it with them and offer to pay toward my brother-in-law’s extravagance. My husband says they had to expect that sort of thing since they picked such a fancy restaurant and didn’t choose a set menu, and we’d just be embarrassing them. Which of us is right? – N

How can someone be the “sweetest guy in the world” who finds ways to get other people – unwittingly – to pay for his indulgences? Howwwwww.

That’s exactly what it means to “game the system.” It’s about taking advantage of someone else. Period.

There is nothing sweet about it.

The idea of it drives me the same kind of nuts as when people declare something a “victimless crime.” Anything that involves taking something from someone else, and that includes even faceless someone elses, even wealthy someone elses, that is not willingly given? That is a crime with a victim. To call it otherwise is to decide you’re just more important than your victim is. Nothing sweet about that, either.

Since I’m all up in your grill with definitions … when one “discreetly ask[s] the waiter to confirm the charges,” one is technically not balking, you’re right, since that means stopping short or refusing and your friends did in fact pay – but it’s a pretty darn good example of flinching. That’s the thing people do involuntarily the moment they realize they’re about to be hit with something painful.

When you’re directly or indirectly responsible for causing someone pain, you apologize.

For your spouse to declare, more or less, that your friends had it coming because they chose to be extra generous has me clutching my pearls so hard I might rip them off and use them to thwack him and his brother both.

Call your friends and say you’re horrified by your brother-in-law’s behavior, of which you are only now fully aware, and offer to make them whole; either way, the next dinner or three will be on you. Also tell your brother-in-law you are upset he took advantage of your friends’ generosity, and let your spouse know you’re doing it; and, finally, when it’s up to you, don’t invite your brother-in-law for anything that involves a menu again, unless you’re ready to pick up the tab.