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The Art Of Flirting

I wanted him to know that I was smart and likable. I wanted him to understand how great I am.

Crush City is a biweekly column following the romantic misadventures of New York City high school junior, Anna Koppelman. Her conquests include studying her crush in geometry instead of isosceles triangles and making a secret Pinterest board for the wedding she is definitely going to have with her older brother's friend. Anna may not be talking to any of her exes, but she’s happy to write about them.

James told me I was a four on the corner of 72nd and Broadway, right outside of the Trader Joe’s. We were in ninth grade, walking to my house from the train. He had blond hair, cut shaggy under his ears. It was like a hipster bowl cut, but somehow it worked for him. He had olive skin and green eyes. He was funny in the way that he bent the entire world into something he could tear down. And I was a four.

It’s a Saturday, and Wes and I meet backstage before our improv show. He is taller than me; he has a slight scruff and the posture of someone who has been spoon-fed the idea that if the entire world saw him, even for the slightest of seconds, all great tragedies would cease, all conflicts would resolve in peace, and estranged lovers would appreciate each other again. For that quick moment, the entire world would be able to agree on one small, simple thing: Everyone would come together to say in unison, “Damn, that boy is hot.” In only the time it takes my eyes to process the sharpness of his jaw and the depth of his hazel eyes and deliver that impression to my brain, I know that he believes this theory, too.

I am in seventh grade. The boy I like doesn’t like me back. In fact, it feels like no boy will ever like me back. I am sad and longing for a first kiss, or even a remote non-spin-the-bottle touch from someone I like. So Erin has me put on two bras, crisscross the straps, pin them together, add bronzer to the curves and highlighter to the tops. She makes my size B breasts look like small Cs, then buckles me into a bright pink tank top. She does my hair, loose curls around a wand iron, and puts on my makeup, heavy on the shimmer. She tells me to get on my bed. To prop my arms under them, subtly give them more of a boost. Bigger shape. My boobs are the marketing campaign she believes will take me to whatever the level after hand-holding is. She holds the phone from above as she begins to snap photos. I am told to look casual.

“I’m, like, really bad at ping-pong, but sometimes I lie and tell people I’m good at it,” Wes tells me.

It’s after the show and we are walking to dinner. Half the cast crowds the sidewalk. People are trying to get past us, rolling their eyes the way grownups roll their eyes at teenagers who crowd sidewalks. I suggest we walk in a single-file line. He tells me that “wouldn’t be very social” with a winky smile typical for his type. I play it off as sarcasm because it kinda was and also because I tend to play off everything I awkwardly do as sarcasm. Now we are on the topic of ping-pong and I’m half paying attention and half freaking out over whether or not I have something hanging out of my nose.

“Well, maybe I can challenge you to it sometime,” he replies.

I text my brother to confirm that this is flirting. It is.

The summer before ninth grade, I lost 10 pounds. I thought this would make my life easier, like suddenly I would walk down a hallway and people would look at me as if I were someone to look at. I cut my hair and dyed it blond, and then ombre, and then back to brown. There was a girl at my summer program with “better” legs than mine. Max, who was Southern and had pink cheeks, liked her. I watched as they danced together the final night of the program. No one danced with me.

I am worried about high school. Someone tells me that maybe if I lose some weight, social things will be easier for me. I feel big in every room I’m in, like somehow I’m taking up too much space. I picture myself small, in a yoga class, drinking green tea or kombucha — whatever girls with better legs and Southern boys crushing on them like to drink. I come home from the summer program with my confidence drained. I learn how to run, and while I run I picture funny boys and their lips as if they’re some type of destination I am trying to get to. I eat a lot of carrots. I don’t feel any smaller in rooms.

I would have hated Wes if I met him in middle school, he tells me, as if it’s some kind of embarrassing brag, before teetering his way into a story about grinding with the wrong girl at a bar mitzvah. The night ended with him getting punched, he says, adding that he wasn’t that great in ninth grade, either. I ask him what changed. He tells me he discovered feminism halfway through sophomore year. I nod. The line feels used, like he learned it in some kind of “how to get in the pants off a teenage New York liberal” self-help book, but maybe I’m jaded, and maybe what the world needs is more teen boy feminists. I leave my bullshit meter at “perplexed.” It is now my turn to talk about middle school.

“I wore a rainbow poncho my mom knitted me every day of sixth grade,” I say. “That sums it up.”

James and I find ourselves on 75th Street. The silence between us weighs heavy on my insecurity. He shifts, almost to display some kind of guilt. He turns to me: “You know, at least your personality is like a six, and if you add those together, to some guy, you’ll be like a ten.” I try to meld this into some kind of compliment.

I hold my arms across my chest, unknowingly trying to hide myself. My dignity is lost to the darkness of the night. We are now outside my apartment. I say goodbye to James, then go up. I get myself to my room before the tears start. I let them run as I take off my clothes, as I stare at myself naked in the mirror, adding the numbers up in my head again and again. “Pretty”: some kind of badge no one will give me no matter how hard I work to get it. I take my makeup off and brush my teeth. I get in bed, let my body curl around itself, go to sleep.

Wes is a photographer, which makes sense since I always find myself crushing on teenage photographers — there is something about trying to capture emotion in a frame that gets me every time. Right now he’s working on a project about shadows and light. He asks me what I like to do besides improv. I tell him I like to write. I tell him about this column.

“Oh, so you can’t have a boyfriend?” he asks. “Because it would ruin everything.”

“No, I would just write about that.”

“Noted,” he replies. I run with the banter, no matter how rehearsed his flirtation feels.

“Ugly” was a fear I held for years, like my worth rested on the number I was given, on the ways my boobs looked in a tank top. I perfected the smoky eye. I learned how to curl my hair. I wished for “pretty” like some kind of magical solution I could pour on my life to turn it into what I imagined it could be. I can’t tell you that this ever stopped completely, that I didn’t hope Wes thought I was hot when he spoke to me, that I didn’t try on a few outfits in an effort to find the perfect mix of “casually not trying at all” and “slightly sexy in a librarian-esque way.” Because if I told you that I no longer cared — that the words thrown around in my past never came back to sting me when I looked in my bathroom mirror — I would be lying.

But here’s what I can tell you: I also worried about being funny. I wanted him to know that I was smart, that I was likable, that I could write. I wanted him to understand how great I am. Because more than anything, what my ninth-grade self didn’t know yet was how great she was. That her worth was more than her pants size or how much yoga she did. That her worth was more than what James told her it was on 72nd and Broadway. That her worth was only limited by what she believed it to be.

I walk myself home. I go upstairs. I think about Wes. I find myself on his photography website. The lights and the shadows do hold meaning, just like he told me they would. I hope that he’ll text me.

But really none of this is about boys. It never is. It’s about me. It about how maybe I’ll text him. Or maybe I won't. If only one thing is certain in this world, it’s that there is always another flirtatious photographer in New York City.

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