Better to just be a penguin at prom

• Mr. Hipster:
• I have been struggling to come up with a good promposal that will get my crush to say “yes.” My biggest problem is that it’s really hard to come up with an original idea. Everything I can think of has already been done, and I don’t want her to think I’m just ripping off some other guy’s Instagram. Got any good ideas? Also, what’s your opinion on a crazy tux?
• — Casey

• Dear Hipster:
• I want to wear a kick ass tux to my prom. I mean, like, anything that’s not a black one because it makes me look like a penguin. But my mom says she won’t pay for it. How do I talk her into letting me wear an awesome tuxedo.
• — Efren

• Dear Hipster:
• How do I get my prom date to not wear a plum tux? He thinks it’s cool because of a stupid movie, but I don’t want to go to the prom with Angus :(
• — Veronica, via email

Now, now, young sir, if I were to gift you a flawless promposal idea, wouldn’t you then be ripping off “some other guy” instead of taking your best shot at winning her over by your own no doubt ample reserves of courtly grace and savoir faire? I must say, your problem points out the weirdness of promposals. When I think of teenagers promposing to each other over Instagram, Facebook, and Twitter, staging elaborate photo and video shoots to “pop the question,” as it were, I can’t help but notice how oddly public the whole process has become.

Don’t get me wrong, I’m twice as guilty as the next hipster of Instagramming a plate of chicken wings just to say, “I ate this.” I can’t deny that a highly publicized life makes sense for the 21st-century soul. Sharing is caring, right? But take a minute to realize that the categorical oversharing of modern life can make private things much more special if you know when to put down the selfie stick and soak up a little life in real time. I wonder, who are you really trying to impress with a good promposal? Your crush? Or your friends online? In this case, it’s not about the likes.

Also, while I’m waxing romantic and early-2000s old fashioned, you young, would-be gentlemen should wear proper tuxedos. Jim Carrey wore the orange tux in Dumb and Dumber to prove that just because you could do something, it doesn’t mean you should. I know, profaning the sacred is in the hipster job description. We call it “being ironic,” and it pisses people off. But the smartest hipsters know where to draw the line. I can’t conceive of a lamer bid for originality than wearing a novelty tuxedo. So over it. Prove your cool by dressing as a gentleman when the situation demands. You are not Snoop Dogg, and therefore cannot wear whatever whenever.

Any other time, all bets are off. You can wear a goofy tuxedo on some random, regular day, and I’ll send 10,000 hipster points your way. Understanding this fine line between innovation and mockery is key to discerning the difference between radness and annoyingness.

Now, go ahead, wring those imaginations dry and prompose your hearts out (if you still want to). But do it for her. Or him. Whatever. And look sharp.