When a co-worker, close friend, or family member goes through chemotherapy, some people shave their heads in solidarity. When my childhood friend broke up with her boyfriend last winter, we both joined OKCupid.

Actually, she made an account first, mostly because her ex-boyfriend already had one. It was free. It was all the rage among 20-somethings, or that’s what The New York Times said. It was fun. (And it was free.)

Her success was immediate. She went on five dates in five days. She had five free dinners. She got a free movie ticket to The Girl with the Dragon Tattoo (not an ideal first-date movie, but whatever). Who needed a meal plan when you had OKCupid? There was an endless trove of men willing to wine and dine her.

It turns out it’s pretty gratifying to have a deflated ego stroked by men with nice abs posing shirtless on beaches. When dozens of strangers tell you how pretty you are—in OKCupid-ese: five stars out of five!—eating a tub of ice cream on the sofa is child’s play.

Clearly, your ex-boyfriend is a terrible person who’s intimidated by your brilliance and attractiveness.

My friend was an OKCupid genius. She was a master of the carefully crafted flirty sentence. She was witty and friendly and didn’t sound creepy. She knew to talk about sports. She even wore a sports jersey in one of her photos. There was a photo of her walking pensively on the beach. I told her she was the OKCupid poster girl.

One night in my basement over winter break, we spent an hour (okay, hours) going over her prospects. When, in my typically pessimistic tone, I remarked that this is what our Saturday night life had come to, our third friend said, with a shrug, at least it isn’t Facebook stalking your roommate’s friend’s older brother’s former roommate. This, at least, could lead to something. Then my friend started making me a profile.

She picked two of my best “I am not a serial killer” photos and left the rest to me.

Taking cues from her scintillating conversations with bros about sports, I followed suit. Under “tell us about yourself,” I wrote “Rooting for the Redskins growing up involved a lot of face palming.” Of course, my knowledge of football was based on my dad’s mood during Chinese dinner on Sundays. But they would never know. Drop a Jeremy Lin reference, and I was golden.

Under “the most personal thing you’re willing to admit,” I wrote about my unapologetic adoration of the show Teen Mom (My exact words were, “I’m addicted to Teen Mom. Sorry, I’m not sorry.”). Referencing teen pregnancy clearly was going to win me major points. Perhaps people would see it as a thinly-veiled reference to my toddler ... or my maternal qualities.

And yet, OKCupid never matched me with the 6’8” heavyweight rower of my dreams. I was a 93 percent match with a 23-year-old straight male from Cambridge, who was balancing a purple platypus Beanie Baby on his head in his profile picture. What did that say about me?

Maybe you should retake your personality survey, one friend suggested.

I was an 85 percent match with a friend from elementary school. We had gone to the same Hebrew school. But I was a jerk, and when his mom called my mom to see if we could carpool to the local synagogue on Wednesdays, I told her I’d rather become a Christian. Or gouge out my eyes.

Forced to live vicariously through my friend, I kept tabs on her progress with Derrick, the law student; John, the short Ph.D. student; and a nondescript man named Ryan.

But then things got complicated. She didn’t actually like most of the guys, and they were all too short. It reminded her how awesome (and tall) her ex-boyfriend was in comparison. Suddenly, she was juggling five different guys, blowing one off for another, courting new ones while casting off the rejects.