It was 2003, and I didn’t know anybody, so I joined a dating website. Back then, OkCupid was beta testing. It was a relatively small community of users, and we used the site more for making our own personality quizzes than we did for actual dating.
I stayed up until 3 or 4 a.m. most nights, carefully crafting tests like, “Which of My Sock Puppets Are You?” and “Which Sondheim Musical Are You?” It was fun, and once in a while I’d meet somebody who’d send me a message like, “OMG, I’m obsessed with Sondheim, and I only live half a mile from you, so you should come to my potluck.”
I made a few IRL (in real life) friends, but I didn’t date anyone from OkCupid. I was a 19-year-old college dropout, and I wasn’t looking for a relationship.
Then one night a new profile popped up on my homescreen. He was a six-and-a-half-foot-tall dude, wearing a fluffy Super Grover costume. I read his “About Me” and found myself interested in him — until I got to the end of his page. It said, “You should message me if you appreciate randomness for the art it truly is.”
I rolled my eyes and started writing the world’s most obnoxious email. I called it, “The Art of Randomness,” and it went on for three incoherent pages about nothing. I speculated that pink clouds at sunset would taste like orange sherbet instead of strawberries, that ninjas would destroy a band of pirates and that my dirty laundry was plotting insurrection against my closet. I figured he’d report me to the admins or tell me I was being a jerk.
What I didn’t expect was a three-page email from him the next day, answering everything I’d said, point by point.
I wrote back, and he wrote back again and so on. For a few weeks, we sent increasingly ridiculous messages, until it seemed we’d reached a breaking point. Either we were going to date or we weren’t. So we picked a night.
He was going to college in the suburbs, and I lived in the smallest studio apartment in the city. On a cold March night, he bought a bottle of wine and took the train into the city, where I was making dinner. From the moment he stepped through the door, it was a disaster. My ferrets, who were running loose, attacked him. The oven turned itself off, and I had to scavenge an impromptu meal while my planned dinner took another two hours to be finished.
We scarcely made eye contact until the moment he realized he’d missed his last train home. When I told him he could spend the night, he assumed I meant spend the night, and we never managed to recover from that miscommunication. While I slept, he lay awake on my living-room floor and snuck out to catch the first morning train before the sun rose.
I was disappointed the date had gone so badly, but when he sent me an apology email, I was relieved. We started writing to each other again, and the letters were fun. We flirted a little but mostly made jokes.
We eventually talked about pretty much everything going on in our lives. Over the next years, we told each other about people we were dating, movies we liked — usually the same ones — bands we were listening to and problems with our families. When he graduated from college, he moved into the city, and I invited him over for dinner again.
This time, things went well. He came over nearly every weekend, and we were like old friends. By the end of the fall we were dating, and by the new year we knew we were in love.
We were married in 2008, five years after our terrible, no good, very bad first date. It has always felt like I married the person I know best in the world, the person who knows me the best. Thanks to nearly three years of being online pen pals, I got to marry my best friend.