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The Roundup

What NOT To Buy Your Boss For Christmas

What NOT To Buy Your Boss For Christmas


We’ve all been there – the awkward office moments before Christmas when you ponder whether or not you should get your boss a gift. Except in very few cases (small-business, super-hottie [more on this later], your existing friend is your boss) you should not. If you decide to throw caution to the wind and get your boss a gift, make sure you exercise your creative muscle; for God’s sake do NOT get anything on this list. Gifts are supposed to be for friends – and people you like – so if your boss falls into those categories, check out The Guy Gift Guide (or just pick up a nice bottle of liquor) for some cool material for the higher-up.


Dummies Books

Instead of buying your boss a Dummies book, just call him an asshole and save yourself the weeks of torment. Firing you would mean a severance package, so he’s just going to torture you until you quit. Best case scenario – your boss chuckles but secretly puts you on the “I’m going to find someway to rationalize firing this idiot” list. Worst case scenario – hello unemployment line. Do you really want to lose your 401k benefits and Christmas bonus? Telling your friends/family/wife that you got fired during Christmas dinner will also totally kill everyone’s buzz. Don’t be the guy that ruins Christmas.



If you are even considering buying lingerie for your boss, CONGRATULATIONS! you are one of a very few lucky men who has a super hot (hopefully female) boss. Unless you have already slept with her and know her sizes, don’t screw up your chances with a naughty underthings purchase. Honestly, when was the last time you bought your significant other lingerie and got the sizes right? If you don’t get the sizing exactly right, there are only two outcomes: either you buy it too big and she thinks you think she is fat; you buy it too small and she is flattered but never wears it because she feels fat. First of all, it’s incredibly inappropriate, but more importantly you’ll probably screw up any future chances of seeing her wearing them (or nothing).


Gift Cards

*YAWN* Gift cards are – by far – the LAMEST Christmas gift ever. Do you want your boss to think you are the most boring, thoughtless, uncreative, lame employee he has? Buy him a gift card. Since you seem to be hell bent on proving all those action verbs on your resume were a lie, buy it for Starbucks while you’re at it. Nothing says “I’m unimaginative” like a gift card for coffee (that you probably buy him on a regular basis anyways).


USB Missile Launcher

Does your boss have an office? Is it out of range of styrofoam ballistic ordinance (approximately six meters)? Do you have remote access to his computer? Do you have job security? If you answered yes to all of these questions you should definitely buy this for your boss because it’s one of those gifts that you buy for someone else but is really for you. You can shoot him in the face with nerf-ish darts a few times before he inevitably destroys it.  When that happens – and it will – you’re only out like twenty bucks. If you answered no to any of the above questions, you are going to be pelted with these stupid little missiles until you start drinking on the job. Remember, never buy anything for your boss that can be used against you in any capacity. Unfortunately, weapons fall into this category.


World’s Best Boss Mug

How far is your head up your boss’ ass? Really? World’s Best Boss? The only best anything in the world is you, stop artificially inflating Michael Scott’s ego. Besides, buying any “World’s Best Boss” schwag isn’t really a gift so much as it is an invitation for ridicule. If, for some reason, you want to paint a target on your back for your co-workers than by all means buy it.


Boss Stuffed Animal

Just because you can get a stuffed animal made of your boss does not mean that you should. Unless your boss is a complete tool he’s not going to keep it in his office anyways; it’s just going to go home with him and become his purse dog’s new chew toy. However, getting a stuffed animal made of your boss is totally acceptable (encouraged even) if – and only if – it is done with the sole purpose of being destroyed. If you and your buddies want to go up on the roof for a “conference call” and take turns eviscerating your boss you should get one… or three. The point is, you should NEVER get one to give to your boss.

picture frame

Picture Frames

Let’s think about this. Do you honestly want to see any more pictures of your boss’ kids? How about pictures of the vacation that he took to Cabo that he won’t stop talking about? Now, if your boss has an extremely hot wife, have at it because everyone in the office will thank you later.


Awkward T-Shirts

Ah, the awkward t-shirt. Yeah, it’s great for your buddies, college roommate, and maybe even your dad. That said, your boss is either going to be incredibly uncomfortable with your purchase or demand you take him out so he can wear it. Either way, you end up screwed. Not in the good way though, because you’ll never pick up chicks at the bar with your boss around…especially if he’s wearing an Alanis Morissette ironic t-shirt that also happens to be mildly offensive.



Do you want to receive a fruitcake in approximately 365 days? Then don’t buy this for your boss. Fruitcakes are like SPAM, no one likes it and it never goes bad. You would be better off buying your boss a slightly less colorful paperweight (get it engraved with his name while you’re at it) just so he doesn’t see it, cringe, and ponder every day why he hired you. You might be giving the gift of fruitcake, but you’re the fruitcake. Back to the drawing board.



If you think there is any way you will get away with this, you have a set of cahones on you the size of Peter Gibbons. You would be much better off just calling your boss fat and saving the $50 because this is just a bigger, shinier, electronic version of your resignation. You know the “Do these jeans make me look fat” question? Try answering that with a scale and see what happens. Now pretend like you don’t have money for beers after the conversation, as if it wasn’t already bad enough.