Of course we all know a "that guy". My husband's best friend is just such a guy. One small favor that is easy to grant, and would be rude not to, always leads to another and another and another. I worked for a CPA for several years and was proficient at income tax preparation. My husband's friend asked if I would help him out in the year he started as an Uber driver. I reluctantly agreed and gave him a list of what he needed to have itemized. Of course, he arrives with a cardboard box full of receipts, scraps of paper, and none of the paperwork I told him he needed from Uber. The one hour job turned into an all day job. He ended up spending the night because he lived about 300 mi away. He insisted on taking us out for dinner (I had no intention of charging him for the tax return) but at the end of the meal his one and only credit card was declined. Sigh....