I made a Boston OKCupid profile four days before I moved there so I could start talking to people and get the lay of the land. Good idea, right? Sounds like fun? Promise me you’ll never do this. PROMISE ME.
I carefully mapped out my Eat, Drive, F*ck route to coincide with the best seasons of each city. So of course I decided to go to Boston in the fall (and Asheville in the winter because I hate New York winters, and Austin in the spring so I’m not there when it’s hot as balls). I was so excited to visit Boston during its best season. And then I went on an online dating site there.
I let people know about my trip in my dating profile so I’m upfront and honest about the fact that I’m just passing through. “How does Boston rank in comparison to the other cities you’ve visited?” almost all of these men ask me. And what I say in return is: “If the Boston OKC scene is representative of Boston as a whole, I will… not be putting roots down here.”
Here are a few first messages I received from Boston bros:
And I'll throw in an interaction from Bumble so you can really see what I'm working with:
Two days before I left, I started complaining to my friend Vanessa. “I don’t think I’m going to go on any dates in Boston. Boston guys aren’t as hot as NYC guys and I feel like a total asshole saying that.”
“Maybe you’ll take the next two months to ‘dry out,’” she said.
“’Dry out?’ Bitch, I’m gonna be jerky by the end of this trip.”
I was actually going to shave my bikini line and run to Babeland before my trip to pick up packets of lube before I left, but after a few days on Boston OKC, there was no use. Just like a home without HBO, there will be no sex in this city. I’ll be walking around prickly and dry, like one of those carpets made of fake grass.
I went over to my friend Dave’s house and told him about my disappointment. A Yale grad and Columbia Business School grad, I cracked up but wasn’t surprised when Dave opened his laptop, said “Let’s investigate this” and started crunching some numbers.
“The population of NYC is 8 million people. Half are men. So now we’re down to 4 million. About ten percent of those men identify as gay. Now we’re down to 3.6 million. And let’s say half of those hetero men are single. You’re used to a dating pool of roughly 1.5 million people.”
That sounded about right.
“Now let’s take a look at Boston. Its population is 600k people. If we do the same math, the dating pool there is about 150k people. It is a tenth of what you’re used to.”
I heard that math and was like FUCK. Vanessa also reminded me that people don’t come to Boston to become an actor or a musician or a model like they do in NYC. Because the thing about dating in NYC is that even though most of the men are kinda sorta man-children who don’t really know what they want, you can tolerate it at least for a little while because they’re hot. And I am a weak, weak woman when it comes to tattooed men with dark hair, which NYC is full of. If I want to get laid in Boston, I’ll have to pretend all these redheads’ freckles are just a ton of tiny brown circular tattoos. Connect the dots? I dunno. I’ll soldier through it.
And then I got here. When I got off the train and was waiting for my Lyft to my Airbnb, a strange man my dad’s age came up to me and asked if we could share a cab. When I told him I couldn’t help him, he called me “really fucking rude” and stormed off. (Ah, just like home. Already I was missing NYC!) That was my first interaction with a man in Boston.
So despite all of the inherent challenges when it comes to the Boston dating scene, I did set up very, very casual dates with three men:
Dana Hamilton is a writer from New York City currently traveling across the United States on her own for all of 2018. Passionate about everything having to do with the body, she writes about sex, dating, relationships, body image, and eating disorder recovery. She is a frequent contributor to Playboy and her work has appeared in Cosmopolitan, Marie Claire, Teen Vogue, New York Magazine, Time Out NY, and SELF, among other publications. Before she became a freelance writer, she was an editor at two "Big Five" houses in the book publishing industry. She has also written four books (under a pseudonym) for HarperCollins and is currently working on her fifth novel. She holds a BA in writing and nutrition from New York University.
Passionate about everything having to do with the body, Dana Hamilton writes about sex, dating, relationships, body image, and eating disorder recovery. She is a frequent contributor to Playboy and her work has appeared in Cosmopolitan, Marie Claire, Teen Vogue, New York Magazine, Time Out NY, and SELF, among other publications. After driving (and dating) across the country and back on her own for all of 2018, Dana now splits her time between New York, Boston, and Chicago. Before she became a freelance writer, she was an editor at two "Big Five" houses in the book publishing industry. She has also written four books (under a pseudonym) for HarperCollins and is currently working on her fifth novel. She holds a BA in writing and nutrition from New York University.