How not to suck at gift giving

This time of year, I always think back to my former life as a paralegal in the Settlement Trial Department of a Big_Bucks Law Firm 1.0 and one of the worst Christmas presents I ever got.   

It was from my boss, a lady who was only a decade older than I yet seemed to have a handle on what was en vogue.  She gave me a set of Dinosaur Christmas lights.  I don't remember exactly how old I was at the time -- 25, 26, maybe 27 -- but clearly I was past my dinosaur toy phase.  These weren't even trendy or kitschy dinosaurs.  This was something you'd put in a 7 year old's room to decorate his window or mini tree.  I was so caught off guard by the gift that I couldn't even feign appreciation.  And honestly, if you give this sort of gift to a kid-less, single guy in his 20s, you pretty much forfeit any claim to a gracious thank you or fake smile.

What is even more mind boggling is that my boss has a December birthday so we all gave her various presents a few weeks before.  Knowing that she liked red wine, I got her a box set of wine.  Sure it wasn't $20/bottle wine but it wasn't 2 buck chuck either.  You'd think this would have set the bar (pun intended) and she might have reciprocated with a nice bottle of Rum or something.

Looking back, I wonder if she re-gifted something she got or had bought for another occasion. I'd like to think that perhaps she had mixed up her gifts.  Someone else got my bottle of rum.  Alas, the simplest explanation is most likely true.  There always was something a little off about her.

I know it's hard to give an appropriate gift to someone, especially in the workplace with all the extra PC minefields.  However, it's not impossible if you put a little thought and effort into it.  All you have to do is consider the person’s hobbies and interests.  That might require having a conversation with them that doesn't revolve around you -- another thing that was hard for boss lady to do.

So the point is that if you feel the need or obligation to give someone a gift, do the ground work to make sure it is something they will appreciate, use or at least re-gift without looking like a clueless jerk.