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The question

My dad received an inheritance and he chose to take the family to Mexico. When he announced the trip to my brother's family, my brother and his wife assumed that their adult children's unmarried partners were invited on the trip and my dad would pick up the $3,800 tab for each partner. My dad does not know the partners and does not consider them family. In fact, one of them he met only briefly once. My dad was stunned that my brother and his wife did not quickly rectify the situation; he felt that they should have known their assumption was unacceptable. My dad stated that he did not want to pay for the partners but "to keep peace" he would. Before the tickets were booked, I advised my brother and wife how my dad felt but they ignored me. I feel that my brother's family is taking advantage of my dad's generosity and it makes me angry. Am I being too emotional?

The answer

Not in my books. That kind of thing really fries my onions, as well.

I find other people's assumptions annoying in general, particularly financial assumptions, and especially the ones that conveniently benefit them.

But, I most particularly and especially dislike the ones that also insult my intelligence.

I tell my Damage Control Master Class: People can and will forgive you almost anything if you play your cards right. They can even forgive if you lie to their faces about what you've done – because they say to themselves: "I might've done the same in his/her shoes."

But one thing people can never forgive is when you insult their intelligence. People hate having their intelligence insulted. That's when the pitchforks and tar and feathers come out.

Let me give an admittedly trivial example from my own life.

Recently, I went to brunch at a swish hotel restaurant with my mother and my wife. The waiter comes gliding over in his starchy shirt and special little apron, all smiley and helpful, carrying a crystal jug full of orange juice: "Would any of you care for some fresh-squeezed orange juice?"

And that was it. Boom: brunch ruined for me. Because he was assuming I am: a) full of clueless assumptions, b) a sucker over whose eyes the wool could easily be pulled, c) meek and compliant. (That I would dimly assume the O.J. was free, and when the bill came and it turned out each glass was, like, seven bucks, having been "refreshed" numerous times, I would meekly accept my fate and pay.)

But, see, I'm none of those things. I used to live in New York, babies! So I said, and I quote: "May I say something?"

Him, still holding the pitcher hovering over the table: "Certainly, sir."

Me (steely glare): "I don't appreciate when I go somewhere in good faith with my mother and wife and the first thing that happens is getting a shakedown and being played for a fool."

And – well, maybe I should just abandon the anecdote right there. Talk about steely glares: you should've seen the one I got from my wife. Somehow brunch was salvaged, but in any case.

Maybe it's because I'm the King of Confrontation (Lao Tzu: "The sage, because he confronts his problems, never has any"), but I don't think you should let your brother's behaviour pass either.

I wouldn't say anything before or during your vacation. Since your father shelled out his money, for the sake of "keeping the peace," he's not getting much of a return on his investment if there then is tension in paradise thanks to a tiff between you and your bro.

So enjoy the sun, have a margarita at a beach-side restaurant with the sand warming your toes (is my envy showing?), nibble some chips and salsa, laugh and play Frisbee on the beach.

But upon your return to cooler climes, I would definitely say something to your brother. To the effect of: "You know, Dad was being really kind and generous by offering to take the family on vacation, and your so-called assumption was pretty presumptuous. Also, it kind of diluted the whole concept of 'family vacation.'"

He might squawk. There might be push-back. But if he has any sense of decency he'll know, deep down, shaking down his own father for Mexican vacations for his kids' boyfriends and girlfriends is a bit thick.

I'd also say something to your father – to the effect that there is a fine line between being nice and being someone people feel they can take advantage of. And it's possible to be the former without necessarily being the latter.

Are you in a sticky situation? Send your dilemmas to damage@globeandmail.com. Please keep your submissions to 150 words and include a daytime contact number so we can follow up with any queries.

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