My Teenage Crush On Conan O’Brien Made Me Into My Best, Weirdest Self

We all had them, those all-consuming crushes that took over our teenage lives. In our series The Objects of Our Obsession, writers explore the deeper meanings behind those fixations, and pay tribute to the people who we found totally crush-worthy.

I’ve always loved staying up late. I love the darkness of a sleeping house, the isolation from my sleeping family, the intoxicating ability to postpone the arrival of the next morning. But the absolute highlight of staying up past midnight on a school night was Late Night with Conan O’Brien.

The few minutes before the show started were so exciting, and yet also so boring. I’d flip between the last few minutes of The Late Show with David Letterman and The Tonight Show with Jay Leno in a futile attempt to make them end sooner; I’d fix a snack on the commercial break between shows, and run to the living room from the kitchen with a sleeve of saltines and a package of cream cheese once I finally heard the first notes of the brassy, drummy, jazzy theme song. I couldn’t allow myself to miss the very beginning of the show, before the monologue, when Conan would walk out all confident and studly, do his signature jump-and-spin, and then proceed to make fun of himself, the world, and anyone with a recognizable name. 

Conan was the perfect man. Handsome. Weird. Funny. Reliably surprising. Willing to risk alienating his audience or guest with a weird or insulting joke. Self-deprecating to such a degree that, for me, the term “self-deprecation” will forever be synonymous with “Conan O’Brien.”

A celebrity crush, by definition, is a longing for something that has no hope of ever taking shape. I knew I’d never have firsthand experience with the head of orange hair that defied all physics. I knew that I’d never be the intended target of one of those sexy-in-a-not-sexy-way growls. I knew Triumph the Comic Insult Dog would never be a guest at my wedding. 

But that was precisely what was so great about having a celebrity crush. There was no need to approach or analyze or react to the situation. There was no situation. I had no reason to face or question the many insurmountable barriers to my love. I didn’t even have to wipe the saltine dust off my chest. 

IRL crushes always, unfortunately, were a “situation,” somehow. The kind where I had to witness myself behave around an IRL crush like alien species trying to fit in with my surroundings. I’d notice my vocabulary change to accommodate some dopey 15-year-old boy, my words slur from nerves, hear myself say things that were not true, or just stare creepily, too shy to say anything at all. At home, I’d press their phone numbers into my phone, not because it gave me any pleasure to talk to them, but because I was desperate to be able to accomplish such a conversation. I’d write talking points out beforehand, knowing my mind went completely blank when I was nervous. It was never remotely chill. 

There is no such personal risk associated with a celebrity crush, because the result is predetermined. There was nothing to lose that I hadn’t already lost by being born into a small town entirely disconnected from the world of Conan O’Brien, (or Heath Ledger, or Usher, or whomever). I didn’t have to worry about what my personality lacked, or the possibility that my gappy teeth were a deal-breaker, or whether or not the bowl-cut dude from detention was looking at my lips while I attempted to speak—a move that CosmoGirl told me could be a “sign that he’s into you.” 

And yet, even though Conan O’Brien was unattainable, my crush on Conan O’Brien didn’t fit neatly into the “celebrity crush” category. Sure, he played off his celebrity status like it was an accident, but he was a celebrity nonetheless—his pedestal was, to me, roughly at Leonardo DiCaprio’s level. But because of the kind of celebrity he was—smart, funny, weird—my own smart, funny, weird self wasn’t completely obscured by the crush. I thought about my self a lot in reference to Conan, actually. He, like my IRL crushes, made me want desperately to improve who I was. Only it wasn’t out of a destructive, self-defeating need for approval. I was inspired. Conan O’Brien made me want to laugh more. He gave me the confidence to do whatever I wanted, not knowing beforehand if it was going to work or not. I wanted to be braver, sillier, more open-ended in my pursuits. I only wanted crushes that made me feel like this, I decided. Like I could find value in my flaws, like I liked the world more, and could imagine a place for someone like me in it.