Hi Sasha,  My older sister and brother-in-law have two young kids. We all get along well. My sister and brother-in-law have combined solid, average, middle-class annual incomes - he works full-time, she works part-time. They live in a small condo in a very well-to-do neighbourhood. They had some financial difficulties a while ago, but are more stable now. They are not big spenders, but neither are they extremely careful with their money. My parents are comfortably retired, and they give my sister one or two thousand at Christmas every year. As well, my sister sometimes asks them to contribute towards big expenses, such as a new car (bought used), summer camp registration for the kids, new bikes, etc.

Just recently, she asked me and my parents to help pay for monthly (competitive) diving lessons for one of the kids. The problem for me is not about whether we can afford to help them out (we can - my parents have a decent nest egg, and I have no kids), but whether they should be enrolling their kid in an optional activity that they can't afford. Or am I a terrible, cheap aunt for not wanting to help out my sister's kid? N

Hm, this one crosses the line if you ask me.  It actually makes me uncomfortable that your sister thinks it okay to ask you to cough up the dough for this.  Sh-t, I mean, if she had asked you to pitch in because her daughter needed a leg transplant, then, obviously, but for diving lessons?!?

Listen, I'm all for children doing as many extra-curricular activities as possible and yes, diving is a wonderful sport to be a part of, but that doesn’t mean you should be the one funding it.   The big problem here is that this isn’t just a one-off request, this isn’t an opportunity to “treat” your niece – this is a developing pattern of expectations coming from your sister, and I think it’s time  you set some boundaries.

The bottom line here is that if your sis and brother-in-law want this for their daughter then they need to absorb this cost on their own.  But I get it… you don’t want to be the c-nt who crushes your niece’s 2016 Olympics dreams. 

So what you need to do is have a sit-down with your sister and let her know that while you can't give her the money, you’re more than happy to lend it to her.  That if things are tight on their end then you guys can work out a payment plan where she pays you back monthly. N, I’m not going to pretend this isn’t hella awkward - it is - but if your sister isn’t totally clueless then she should get the hint.

Hope this help and thanks for writing in!  Keep sending in your Life + Style questions to [email protected]!