Cheeky imponderables

Let’s get the New Year rolling with some cheeky imponderables, shall we?

Dear Hipster:

What is the difference between cashing in and selling out?

— Dan

It’s like the difference between making your dreams a reality and trading in your dreams for someone else’s. More pointedly, when the world discovers your coolness, and wants to pay you for it, you’re cashing in; but if you’re piling on to someone else’s coolness hoping for a piece of the pie, you’re selling out.

Dear Hipster:

How do you tell whether people are laughing with you or laughing at you?

— Lauren

If you don’t get the joke, it’s all too often the latter.

Dear Hipster:

Should I stay or should I go?

— Joe

That depends almost entirely on whether or not you brought your own beer.

Dear Hipster:

How many hipsters can dance on the head of a pin?

— Devin

The average pin holds ‘n’ hipsters where n = ((t)(y) - 1) / x.

In the equation, ‘t’ represents the time you heard about the underground party. ‘y’ represents the number of people who heard about the party before you did, and ‘x’ marks the spot where the band started playing Lynyrd Skynyrd covers instead of their original tunes because some asshole yelled “Play Freebird!” at the top of his lungs.

Dear Hipster:

What was before the Big Bang?

— Eve

Whatever it was, there’s some insufferable hipster out there who has been “over it” ever since matter started expanding outward from a super-condensed gas state, coalescing into the known universe over the course of a fourteen-billion year cosmic ray-fueled bender. If you listen carefully to the cosmic microwave background, you can faintly hear a nonplussed voice whispering about how “pretty much everything after Singularity” is too mainstream.

Dear Hipster:

What happens if an unstoppable hipster meets an immovable, mainstream basic bro?

— Larry

They collaborate on a pop-up “experience” where you can get Michelob Ultra micheladas, do some CrossFit, and listen half-ironically to that Disturbed song that goes “ooh wah ah ah ah!”

Dear Hipster:

If a hipster barber charges $45 to shave a hipster who doesn’t shave himself, but he charges $48 to shave a hipster who does shave himself, then what does the barber charge himself for a shave?

— Ed

Trick question. He gives himself the “industry discount,” and trades for a quart of handmade kombucha and a copy of his mixtape.

Dear Hipster:

If a starving hipster can only choose between a roast beef sandwich and a ham sandwich to prevent his death by starvation, but he’s not eating gluten and/or on a keto diet, which sandwich does he choose?

— Brad

Simple. He eats both sandwiches, suffers intolerably, pens a heartfelt jeremiad to the unavailability of breadless lunch options in his local urban community and publishes it in the local alt-weekly, attracts funding through a carefully orchestrated Kickstarter campaign, develops a line of artisan lettuce wraps, sells the idea to Starbucks, profits enormously, and ultimately produces a short biopic called That’s a Wrap! How One Man’s Lettuce Vision Changed America.

Some might call it cheating, but I call it “thinking outside the box.”