Do you know how to be cool?

I just want to be a part of the coolness zeitgeist

If you like Bad Advice consider helping Worcester Sucks pay for its continued existence!!

Thank you!!

Dear Shaun,

Do you know how to be cool? Every time I think I am doing something cool, or I feel cool for doing something, I end up feeling self-conscious or worse—like a hack. I just want to be cool. I don’t have to be at the beginning of a cool movement or even be a trendsetter, I just want to be a part of the coolness zeitgeist. Do you know how to do that?

- Joe Hopefully Cool

Dear Joe Hopefully Cool,

That first sentence made my blood boil. It felt like an indictment. I read it and was like “hang on, pal!” But so it goes for someone who has been bullied their entire life. I immediately assume that the thing you are saying to me is an attempt to hurt my feelings. Fun fact, my wife proposed to me and the first thing I thought was that she was negging me. Naturally, no one would want to get married to this pushy, neurotic, sometimes funny person. That would be too much for their own psyche. Yet here I am happily married with a son in a house. Stop judging me, please.

I think this is part of your problem, too. Our minds seem to be on similar wavelengths. If I wasn’t taken, I’d be open to you asking me to get married. Is marriage cool? This is the conundrum.

I think you are asking less about how to be cool and more about how to stop thinking about whether something is cool. The word vibes gets thrown around a lot now. Sport analysts, music reviewers, and fashion blogs can build whole careers on telling the public whether the thing they are writing about “fits the vibe check.” Imagine considering yourself a professional and write down hundreds if not thousands of words about the new Taylor Swift album and the vibes it gives off (Obsessive is the vibe she gives off).

Truly the best way you can be cool is to make a choice. Make a choice and show the world in an outward facing way you do not care about that choice because it makes you happy. Felon Sam Bankman-Fried, who defrauded a ton of folks, had this very manipulative casualness that drove me fucking crazy. He always wore shorts, wrinkled shirts, and had a haircut that seemed as though he rarely cut it. Before big meetings with investors, he would train a camera on his desk in his office. The camera would feed into the boardroom where the meeting would take place, and what would the folks waiting to meet him see? Sam, taking a nap. Then, very performatively, Sam would wake up and the people who were waiting for their late host would supposedly “watch in awe” at this very relaxed and chill CEO. This made me sick to write down. All of this is calculated, and all of this could not have truly made him happy. That is not a choice that makes you happy.

If you want to wear jumpsuits and that is the thing you like to wear, do it. The confidence will ring true. This feels like something a third grade teacher would say, but I think it works. Only you can control how others see you in the world. That’s cool. True coolness.

One caveat to all of this. I am a dad, and the things dads think are cool are inherently not cool. It is in the dad DNA. It just happens. So take this with a grain of salt I guess. I am going to go over here and dab while sharing Facebook videos of Reels that were originally Tik Toks, and talk to your friends about my grill set-up while you’re getting ready.

Send any and all questions to woocomedyweek@gmail.com with the subject line "Bad Advice."

NEWS

Some fun things this week! Tuesday as always is the Live Forever Open Mic at Ralph’s Rock Diner. Sign up is at 7:30, show starts 8:15ish. Then Friday we have Hot Dog! This is one of my favorites to do. Comics spin a wheel to find out their set, and we really try to throw some wrenches in there to get the very best stuff out of them. Plus it is free! Poster below. Then, on Saturday I am at Democracy Brewing in Downtown Crossing in Boston. Tickets for that show are here. Sunday I’ll be opening for Sammy Obeid at Laugh Boston. The early show is sold out, but there are still tickets available for the 8:30. I’ll be back at Laugh Boston on Tuesday 4/30 opening for Scottish comedian Gary Meikle. Fun stuff! See you out there!