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The question

My wife's brother is a bully, the kind of guy who makes hurtful comments that are way out of line, thinly disguised as "jokes." When one takes offence, he retracts the comment, feigns surprise and asks forgiveness – but the cycle quickly restarts. I've encouraged my wife to stand up to him. When he pushes too far she politely but assertively tells him he's out of line and to back off. Now his wife is calling my mother-in-law to complain about what a witch my wife is. Who does that? When I try to limit my wife's contact with her brother, her mother guilt-trips her into spending more time with him. I know family is important but so is respect. Life's too short to spend around jerks who don't appreciate you and whom you don't like – even if they're siblings. What should I do?

The answer

I know what you mean about bullies who disguise their insults as "jokes."

Passive-aggressive bullies always find cloaking devices for their zingers. Take, for example, the "insultiment" (insult + compliment = insultiment): "Oooh, those glasses look good on you, they really distract from all the weight you've gained recently" (actual, real-life example once directed at me).

Or the "questionsult": "Oooh, so you finally got new curtains? Were these your first choice?" (Also an example from real life – a neighbour who would come over looking for decor flaws, of which there are plenty chez nous.)

In male culture it can be tricky because we will often, to the everlasting astonishment of womenfolk, communicate our affection toward each other through insults. We "bust each other's chops" – and it can resemble rudeness.

It's a question of intent, however. In most cases, there's no ill will. But, to paraphrase Supreme Court Justice Potter Stewart's famous dictum re: pornography (hard to define but "I know it when I see it"), you know a comment intended to hurt when you feel it.

As to what you should do – well, it's a bit of a tough one because you've already tried a few gambits I might normally have suggested, including a) politely but firmly push back, b) take evasive action, and c) keep encounters with the brother-in-law surgical.

And none of it has worked, partially because of the added complication of your mother-in-law running guilt-tripperference (just when you think you're out, she pulls you back in again).

I think it's time for you to step into the fray, sir – and fray it may well be, and result in some frayed nerves.

The only way I see to break this cycle is for you to get up in this bullying brother's grill and tell him how his treatment of your wife makes you feel. Make it clear he's crossing a boundary with you.

I did this recently with a kid I felt was bullying his mother. The setting: a dock at a cottage. I was reading a magazine, sipping a Caesar. She was putting up with the kid's insults and rudeness, for whatever reason, but after a while I realized it was hampering my enjoyment, so finally I leaned forward and said: "Listen, kid, when I'm around I want you to talk nicely to your mother because when you don't it bothers me, you understand?"

The kid was brought up short, for sure. Then I looked at the mother and said: "Listen, I know I'm stepping over a parenting line there …" But she seemed genuinely appreciative and grateful.

Likewise, this problem may seem to be mainly between your wife and your brother-in-law, but viewed from a different angle it's also a problem between him and you (or else you wouldn't have written in, right?). If your wife has a bully who won't back down – well, to me that's a call to action, brother!

So next time this boorish brother drops an insult on her, tell him you don't like it. (Of course, get her permission to do so first.)

If he tries to laugh it off and say it was just a joke, tell him you feel like it was a zinger wrapped in a jokelatey coating, and don't let him off the hook.

Yes, you may feel like you're bullying him a bit. But hey – sometimes that's the only thing bullies understand.

And yes, there may be squawking and friction and a flurry of phone calls between your in-laws.

So what? There's already plenty of that anyway – and only one direction this whole thing is heading: toward further family friction.

And what you're laying down is the truth. You know it. He knows it. Probably deep down his wife and mother do, too.

And as they say, it should set you free, one way or another.

What am I supposed to do now?

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