Dear Claire,

My sister-in-law owes me quite a bit of money, but she has not mentioned anything about paying me back. It’s been a few months, and anytime I bring it up, she changes the subject. I have some expenses coming up and I need to have the debt paid – how do I ask her without causing tension?

Best,

Sad Sister-in-Law

Dearest SSIL,

Oh, my sweet smoked turkey sandwich, this is quite a conundrum! Everyone knows that an outright request to pay the debt is very new money, so you have some fancy tap-dancing to do; I suggest to you shine up your tap shoes and don your sequined top hat! No, no, that was just a funny – metaphors are lovely, yes? Getting back to the matter at hand, you must be sneaky if you want to reclaim your lost finances. Do you have a pair of black jeans? A black long-sleeve tee shirt? Black socks and shoes? A black ski-mask? You don’t? Well, lucky for you, Target has a large supply of all of these goods in many sizes. So, the first step is to visit your local Target, but make sure it’s not with your sister-in-law! That’s a significant obstacle to overcome, because everyone always wants to go to Target all the time. If she asks to accompany you, tell her you are making an intimate purchase that demands privacy and discretion. She will draw her own conclusions (which is her cross to bear) and grant you your solitude. Once you have made your purchase, put the outfit on and discreetly follow your beloved sister-in-law around until she visits an ATM (that stands for Aha, There’s Money). Once she’s there, leap out behind her and demand the money, using an Australian accent to mask your voice – the Aussies are all hoodlums and mavericks, everyone knows that. Terrified, she will have no choice but to give you the money right then and there, without ever knowing it’s you. Now, my motto has always been ‘better safe than sorry’, so have a follow-up plan handy in case you don’t execute the plan flawlessly. If any nosy detectives start to investigate the “robbery” (wink), you will already have an excellent Target-based alibi, but go even a little further. Plant some low-level controlled substances around your sister-in-law’s house. It will cast a lingering doubt on her credibility, which will be handy if you ever need to recoup additional money from her in the future.

There’s always a chance she will repay the original debt later on – BONUS MONEY!!!! Use it buy more wonderful products from Target!

Cordially, Claire