Hi Sasha, I'm looking for an impartial opinion regarding how to deal with family, money and when to give tough love. I'm a graduate student (self-funded/scholarships/generous maternal grandparents) so money is a little tight and I'm counting down the next four months when I'll be able to really look for a full-time job. My Dad lost his job over a year ago. I wanted to be patient with him, knowing he hadn't taken a real break or vacation in the past 8 years and that if he didn't he'd be heading for a nervous breakdown. But here we are year later, and he's knocking on my door asking for money.

I'm struggling with how to motivate him to push harder to look without making him feel bad. I also don't want to become the constant bailout (especially right now, when I don't necessarily have the money to lend). Is this the time to stand-my-ground and push the people I love to be better? Or to I shut-up and write the cheque?


If it makes you any feel better P, half of my friends have been, or are currently in a similar situation; it’s a major emotional tug-of-war because you want to be a good daughter/son but you also want to get the f-ck on with your life.

Now everyone’s deal is a little different and how you choose to react depends on your relationship with your parent, but so far it doesn’t sound like we’re dealing with a Michael Lohan, right?  Sounds more like your pops has fallen on tough times, and if that’s the case then I think it’s your daughterly duty to help him out in whatever way you can.

Emotional support is a given, so to answer your first question P, yes, I do think you should be there to motivate and inspire him to get back on his feet. But keep in mind, your dad ain’t no spring chicken and it becomes exponentially harder to get a job over the age of 50.  

Getting back to the question of financial support, if you have some money stashed away - which it sounds like you do - then you shouldn’t even think twice about it. Obviously if he starts spending it on things that are not necessities (gambling, drugs, hookers) then cut him dry, but if this money is being used to cover some basic living expenses then it’s time to do a direct deposit.  I know it sucks and I know it’s your money, but if he needs the help then you can’t turn your back on him.  

I hope this helps and keep me posted, xx