It’s crunch time. I’m only halfway done with my Holiday shopping, and don’t particularly care. These are all just items and objects. This is the luxurious kind of stress.

Shopping for my friends and family is no problem. I know exactly how to satisfy their needs and tastes. However, most of us have people in our regular lives we’re not close to, but have that obligation to buy holiday gifts for. Constant-contact co-workers, lovely neighbors, great new acquaintances, etc. These are the types who used to be responsible for my worst retail angst. Cologne? Lotion? Gloves? Xanax? A decorative basket filled with tangerines and Triscuits? How the hell do I know what they could use, when the only talking we do is small?  

Many years ago, it all became clear to me. Chocolate or wine. If I teach you anything, let it be: when in doubt, gift chocolate or wine.

Neither are unhealthy, neither are as impersonal as a gift card, you never need to pay more than $25 for either, and - most importantly – you get the peace of mind that neither will go unused. Even if it turns out the people you give the chocolate or wine to don’t eat chocolate or drink wine, they’re sure to know at least one person who does who they can re-gift it to (while making themselves look good in the process). You don’t have to worry about your money going to waste.

One Holiday Season, my first NYC boss at my first NYC job got me an Armani Exchange scarf. “That’s a little extravagant,” I thought, “We ain’t tight. But, so what, he’s rich and I do so much for him.”

He left the tags on. That scarf came off the A/X clearance rack, after getting marked down about 5 times before a final price of something like $21. The following year, he got me this: