You better not cry
Ear Pain

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A gift for their child that looks awesome, yet takes many, many hours to assemble. (Insert2Quarters)
My husband and I were the first of both our friend groups to have kids. His best friend has consistently gotten our daughter Christmas gifts that are either huge (we live in a fairly small condo) or really, really loud and obnoxious.
I’m just biding my time until he has kids of his own… I’ll have my revenge. I’m thinking drum sets, singing dolls, small collectibles that they’ll keep asking for more of, maybe a ball pit. (Platypus211)
Off Balance

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I gave my boss a “World’s Okayest Boss” Mug from http://www.worlds-okayest.com last Christmas because of a reddit post I saw. He thought it was hilarious but it wasn’t really a joke. He’s kinda like Michael Scott without being funny or loving.
This year I plan on trying out something from Trick Mugs, which is full of prank coffee mugs. (chipdumper)
No Cash Value

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A gift certificate to an out-of-state boutique that has no online shopping and is only open M-F. Oh and make it for a high end equestrian equipment shop even though you have never ridden a horse and have no interest in them.
Not that I have any experience with this. (bonkette)