Handout thorny topic for brother

Hi, Carolyn: I’m getting ready for a family vacation. My grandmother has generously offered to pay for a beach rental.

Unfortunately, my sister-in-law just lost her job, and she brought in half of my brother’s family’s income. I am very sympathetic; I was out of a job in 2010. However, every time I suggest an activity – e.g., barbecue at our favorite restaurant – my brother says they can’t afford it, and I say, “Don’t worry, I’ll pick up the tab.”

Frankly, it kind of goes without saying at this point that I’ll be paying for pretty much all of their activities/food that week. I don’t mind, but I would just love for my brother to spare me the guilt trip. He says no to everything I suggest, with repeated reminders of his wife’s unemployment, unless I offer to pay.

It’s my family’s one week of vacation this year, and we’d like to enjoy it. Any suggestions? – Surviving a Family Vacation

Since it’s somewhat confrontational to answer a question with a question, I’ll let an imaginary brother do it for me:

“What do I do about a sibling who knows my wife lost her job – and with it half of our income – but keeps asking if we want to go to this restaurant or that activity, all of it costing money we don’t have? S/he offers to pay, but only after putting me in the position to say I can’t afford it. Being broke is bad enough; I could do without the added mandate to grovel.”

Also known as, if you don’t like the result, then stop doing the same thing over and over.

How about this to break the cycle: Either it has to go with saying that you’re happy to pick up their tab for whatever the family does during the vacation week – meaning, you issue a blanket “My treat for everything” to spare your brother the humiliating he-says-no-then-you- offer-to-pay dance every time you suggest something – or take a hint and serve up some ideas that don’t cost anything.

I’m sure at this point your brother would be thrilled to be able to say “yes” without accepting a handout.