Question: My neighbor keeps calling me and texting me in the middle of the night that he’s locked himself out. I finally got tired of letting him in and told him that he needed professional help. Now he’s left town and expects me to look after his pets, but instead of asking me upfront he just left a key over the doorframe with a note “Hey, if you don’t take care of my cats, they’ll die a horrible slow death of hunger and thirst, but no pressure.”

Answer:
You are correct, it’s a setup. This is the game called “Holding the Bag” or “Hot Potato”, essentially an exercise in Mutually Assured Destruction (MAD) where both players fault out. Why someone would want to play this is probably best left to the psychologists. It’s actually a form of blackmail, except without the cash profits. DO NOT pick up that key. It’s like picking up the monkey’s paw: once you do, a deadly curse falls on you.

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Question:
What do I do when my manager puts himself down in front of me? He does a lot, like he’s angling for some reaction.

Answer:
This is a classic double-bind. If you agree, you’re essentially saying he’s an idiot. If you disagree, that’s insubordination. I’d deflect the remark with some clever non-sequitur like “Did you know cats can vomit at will?” and wait a beat. Then look away and say, “So, about the project plan…”

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Question: Our work team has these long in-person conference meetings and I can’t seem to stay awake. 
Answer:
Sometimes, the appearance of being awake is enough, in which case Salvador Dali has some interesting gadgets to prop open your melting eyelids.

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Question:
So I joined this great new company and promptly got a huge crush on the head boss. I really like working there. He helped me out during a life emergency, too. We danced around the whole professionalism thing and hooked up for a minute, kind of while he had a live-in girlfriend. And yet, if I had to ask myself “Would you rather have him come over for a booty call, or should he finish that damn permit submittal?” I’d of course say get the fucking permit.

– Feeling Like a Side Dish

Dear Side,

You already know the answer to this one: DTMFA. Your guy is essentially married to his business, which is actually how it should be. There’s this clip from an old Charlie Chaplin movie where he’s roller-skating on the edge of a balcony, blindfolded, backwards, looks like he’s going to fall any second but somehow he escapes at the last possible moment, over and over.

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Question: My bank is trying to loan me money that I don’t really need, offering me all sorts of free stuff. Is there some sort of hidden catch here?

Answer:
Let me tell you a story about the legendary Jewish town of Chelm, a village of fools.

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Question: Are self-driving cars really safe? Or should we just quit driving and enjoy the inevitable?

Answer:
A tool is only as good as the user and in this case the “user” controlling them is some corporate entity far away from the action. Consider, however, the amount of automation already in our lives, one example being “the grid” or our electrical infrastructure. It just… works, right? Most of the time, anyways.

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Question: People keep asking me for my honest opinion, but I’m pretty sure that candor will just get me shouted at – again.

Answer:
Present an opaque yet plausible reason that appears factual but, upon closer examination, contains no actual information – or which, upon later examination, could be taken either way. This process is called “opaquifying” and it’s like liquefying, but cloudier.

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Question: I’m feeling stuck and burnt out, but the pay is really good and I’m afraid that if I leave I’ll end up regretting my freewheeling ways.
Answer:
You’re in a gilded cage, and there’s no easy answer here. It’s really your choice, that’s what freedom means… right? To stick with what’s safe and prudent, or to take a leap into the unknown and risk a train wreck. Also note gilding is not solid gold, so you could be clinging to something that’s not even worth much in the end.

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