How To Be Sexy, I Think

Over the course of my life, I’ve learned how to be tactful. I can also be stoic or compassionate or erudite or encouraging. I’ve spent a lot of effort in the last few years figuring out how to be assertive. But, after 27 years, I am still unclear about how to be sexy.

I can usually identify sexiness when I see it in other people. It’s easy to spot in women. There are lots of signifiers. Thanks to advertising, women know that when they want to be sexy, they can put cylinder-shaped things in their mouths. Maybe I’m wrong about that one, though. Personally, I think women are sexy when they put on glasses and pin their hair up. I watch She’s All That backwards.

With guys, there’s a little more of a gray area. Men have to walk a very fine line between sexy and creepy or sexy and hilarious. A man is always teetering on the precipice of sexiness, vulnerable to the winds of fate and fashion. Example: A guy with a dress shirt open showing a little chest hair is sexy (I think?). A guy with a track jacket open showing a lot of chest hair is a landlord (I know for sure). It’s a subtle difference but an important one.

As far as I can tell, being sexy breaks down like this:

Being In Shape

Men have it so, so easy here. Women have so much pressure to attain an unreasonable physical ideal. My girlfriend expressed real concern that one of her breasts was larger than the other. And no matter how many times I assured her: “Sweet! That’s bonus boob!” she could not be consoled.

A man doesn’t have to be a Greek God. He just has to accomplish daily activities with a minimum of wheezing. Here’s exactly how in shape I am. If we were being robbed at knifepoint, I would not be able to fight off the attacker. But if you were in reasonable but not great shape, I would be able to run away alongside you as we fled. You won’t have to worry about my falling way behind. That’s all I ask of a woman. Being able to literally run away with me. It is not sexy to watch someone getting stabbed.

Sexiness, I think, is being in shape enough to stay alive.

Being Confident

Everyone says that confidence is key, and if you don’t have it, you should fake it until you make it. I have trouble doing that. Where do I begin? At the introduction? “Hi, my name is Josh, and I am very sexy. Trust me.” Gross.

The most confident person I’ve ever known is named Jude. He is a great guy. Smart, thoughtful, creative, and wildly confident.

When I met Jude, he was homeless. Every week, he would come to an open mic I hosted in Somerville, MA. He would sit by himself and watch the comedians. One week, after seeing an especially self-deprecating night of open mic comedy, Jude asked for a chance to speak. When his turn came, he took the stage with total poise and control. After staring down a barroom full of comics, he gave a speech, which I will attempt to recreate from memory:

“You. Pathetic. Losers. You’re complaining about not getting laid? I’m bringing home a different girl every night, and I sleep in a graveyard. I live amongst the dead.”

Then he banged the microphone against his forehead until he was bleeding and walked out of the bar.

After he had left, I stepped onstage and addressed the crowd.

“Thank you all for coming. I think we learned a valuable lesson tonight… and that lesson is… women love confidence.”

Men also like confidence. It’s hard to make friends with someone when he or she is always hiding behind stuff, like sarcasm or furniture.

If you live in a cemetery, own it. That’s sexy. Right?

Being Cool

Being cool is mostly about relaxing. Going with the flow. Not being a dweeb about things. Tom Cruise was sexy in Risky Business, and it was mostly because he was the only high schooler who was down with having a brothel in his parents’ house. People like Zooey Deschanel in things because she’s like: “Relax! I get it! I’m a weiiiiiirrrdoo!”

I’m more like: “I’m a weirdo. Is that okay? I could be less weird, maybe, if I tried!”

Also, be cool about other people. Don’t be uptight. Racism and homophobia are not sexy. So is trash talking something that might be your new acquaintance’s secret passion. I’m much better at being cool in that way. (The exception is I will always laugh at two people on a tandem bike.)

Being judge-y is not sexy. If it were, people would role-play in black robes and powdered wigs.

Just let people do what they want to do, if what they want to do is be sexy. I’m not sure what that means. It just sounds like a thing Justin Timberlake would say.

Those are my best guesses at how to be sexy. But as someone unwilling to get in great shape, unsure of how to feign confidence, and unable to relax, I’ll just have to keep hoping that I can appease my girlfriend with baking and backrubs. Wish me luck, guys with abs! TC mark

image – Applegurl

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  • Sarah

    For me, one of the biggest sexinesses is intelligence. If you can teach me something about the universe, then I’m all yours.

    The talent, skill, and well-roundedness to carry a conversation is a derivative of this.

  • Guest

    love your writing!

  • meredith

    One of the best I’ve heard in ages! Had me laughing out loud, but a good message. Nice work!

  • GUEST

    One of Gaby Dunn’s boobs is bigger than the other and now WE ALL KNOW, thanks to YOU, JOSH GONDLEMAN!!

    • Josh Gondelman

      HEY! SHOW SOME RESPECT! DOROTHY MANTOOTH…ERR…GABY DUNN IS A SAINT.

      • GUEST

        PATRON SAINT OF LOPSIDEDNESS

        IF YOU WERE MY HUSBAND I’D GIVE YOU A STERN TALKING TO ABOUT THIS!

    • Anonymous

      Every lady has one boob bigger than the other! EVERY LADY EVER. EVEN YOUR MOM!

  • http://www.facebook.com/grc15r Gregory Costa

    Debbie Harry circa 1978 = epitome of cool.  Effortlessly cool. 

    • Domino

      cool and sexy as fuuuuuuuuuck

  • EB

    I love this man more with every post.

    I would argue, however, it’s easier to understand how men can pull of sexy (see: NPH in how I met your mother) and wicked hard as a woman. 

    • guest

      NPH: not sexy.

  • Guestropod

    well I feel attracted to you based on your TC articles

  • Anonymous

    Love it. Also, gotta love Slummerville. My ma’s from there.

  • http://twitter.com/laurajaynemart laura jayne martin

    Awesome. “Tandem bikes: the best way to end a first date.”

  • http://twitter.com/SoosSahar Sahar Soos


    I’m more like: “I’m a weirdo. Is that okay? I could be less weird, maybe, if I tried!”” << that's me too!! 
    HAI GIRLFRAAAND!! 

  • Brideshead

    Grimes, is that you?

  • beatrice

    “You. Pathetic. Losers. You’re complaining about not getting laid? I’m bringing home a different girl every night, and I sleep in a graveyard. I live amongst the dead.” Reeks of brad pike tho..

    • Oliver Miller

      That was great.

  • http://www.facebook.com/discobiscuits93 Kayla Ann Stockman

    Hi. You’re cute.

  • Elaine Huang

    “My girlfriend expressed real concern that one of her breasts was larger than the other. And no matter how many times I assured her: “Sweet! That’s bonus boob!” she could not be consoled.”
    Universal girl concern.

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