Some of us have talked to our families about money since early childhood. How much allowance can I get? Will you buy me this toy? Why do you pack our lunches? Why do you have to go to work? Are you paying for my college? Then one day, when we've supposedly grown up and are on our own, we get out of practice. It becomes as taboo as our sex lives. We suddenly remember how family money conversations are the crux of every fictional family drama from Jane Austen to Gilmore Girls, and we'd like to avoid all that, thank you very much.Then again, what's money for, if not to help your loved ones?So, deep breaths, you might just have to step into this minefield. Whether you're the one in need of a little cash bailout, or you find yourself in a position to help others, broaching the subject with family won't be easy, but it can be done. The holiday season is as good a time as any to do it — especially if you're all feeling warm and fuzzy about each other (with or without some liquid courage). With the advice of Refinery29's financial expert and founding partner of StashWealth Priya Malani, we've got some guidance to make it all just a little less awkward.