Gift giving can be tricky enough when the recipient is someone you know as well as yourself, see on a regular basis, and can sit comfortably in silence with. But, when it comes to those people with whom your relationships are a bit more complicated, nailing down a thoughtful and appropriate present takes some finesse. So, we called in an expert for the task: Simon Doonan. While Barneys New York
's creative ambassador-at-large might have the taste and knowledge of the market to cherry pick a gift for anyone in your life, he’s also one of our favorite quick-witted straight shooters. In other words, he's the kind of friend you'd text first when you find out your ex is coming to family dinner because she has nowhere else to go on Christmas day. Feeling uncomfortable yet? You're in the right place. Ahead, a few more tricky, awkward gifting scenarios we asked Simon to help us power through.