New York in 24 Hours, or Low-Stakes Dating…Or Actually, Both

Man, I could spend waaay too many hours stroking New York City’s ego. I’d wax perpendicularly about the view from the Empire State Building. I’d shout from the rooftops about sailing a boat on a tucked away lake by the Alice in Wonderland Statue. And the library? With the exhibit about lunch (yes, lunch!) — ooh-la-la. I was verifiably in heaven, with Megan as my tour guide. Grouchy people who laughed when I asked if I would get my pocket knife back after it was confiscated at Ellis Island, good food around every corner, and the candid photo opportunities at Grand Central Station (not to mention every nook and cranny of the city) — yep, heaven.

Of course, I did have a task at hand, and that was to date. Rehan is a lawyer (my first lawyer!) who suggested we meet at the High Line — which was on our to-do list anyway, so already I liked this guy. He picked a place where locals go but that tourists think is rad, and he offered to bring the world’s best hot chocolate, too. I kind of felt like Rehan was the East Coast, male counterpart of me. And it wasn’t just the hot chocolate.

We started walking and talking and pretty quickly delved into the datingverse after he asked what spurred the trip and why I’m on the road.* And we discovered we have the exact same dating style, especially when it comes to first and second dates. Get to know someone as a person, then worry about dating them. Decide if you want to see them again, not if you want them to be your lifelong partner. And then see them again if you want to, and go from there. Expect friendship. Keep the stakes low. Every time one of us made a point about dating, the other would say exactly! and it was a bit like he’d been hanging out in my head with me over the past few months.

To make matters even more similar, he said he once went on a car trip after an especially hard break up, too. He didn’t film it or write about it, but he did travel for two weeks going city to city, staying with friends and just seeing the country. Rehan had hoped the trip would be cathartic but found it at times to be a terrible idea. He was alone and if he didn’t want to be, he was stuck being alone until he got to a friend’s house, at which point sometimes he was ready to be alone. (Ah, the breakup beast rearing it’s indecisive, angst-ridden head. Yep, been there). There was ultimately too much time to think and not enough time to think all at the same time.

And then Rehan asked me if I felt my trip was cathartic.

It’s funny. I’m not sure catharsis has much to do with the road trip anymore. I know at first, when the very idea of fifty/fifty came about, it was from a deep need to get out of dodge. To run away from everything, to see the world and to become different because I knew buying new clothes and reading new books wasn’t going to make me feel different enough to stop having a visceral and emotional reaction to the breakup I’d gone through. I’ve never been good at goodbyes, and I don’t think a breakup goodbye comes any easier to me than anyone else. I feel the shit out of my feelings.

And the very nature of this trip has ensured that I spend a strange amount of time talking about my ex (in and that I tell the breakup story almost every day) and that Megan and I spend a lot of time talking about all my previous relationships to some degree. There are days none of this gets to me and it all feels like water under the bridge, and there are days I feel quite confused and disappointed.

Like Rehan’s roadtrip experience, fifty/fifty is both cathartic and not cathartic. I almost feel like I won’t know ‘til I get back home what the answer is.

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*Every date asks this. You can already envision a montage in the movie of me telling the story, each couple of words a new clip in a new place. It’s not bad, it’s just sort of funny, and I expect to be asked — I’d want to know too, if the roles were reversed.

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