When it comes to sex toys, I’m Mary fucking Poppins. My bag is full of all sorts of tricks. I’d make a joke about how it’s a carpet bag but I’m exhausted after this week.
When packing for two months, I had to fit most of my life into one suitcase that I’d lug onto an Amtrak train. I reserved premium space for things like vitamins and my acupressure mat because I am ten thousand years old. I also brought books and beauty products (hellooooo Korean sheet masks) and workout clothes. But what I didn’t leave room for were toys. I left pretty much my entire collection behind because I didn’t think I was going to get laid here.
[Narrator voice]: That turned out to be a huge mistake.
Remember how I said I was going to be prickly and dry the entire time I was in Boston? Welp, I just had to wait a few more days until the beautiful, smart, successful Harvard/MIT motherfuckers came out of the woodwork.
I told my friend Zoey about all the hotties I've been encountering on Bumble (which has always been the app with the most attractive men, tbh):
Here’s the thing about Boston—everyone looks like they just popped out of an LL Bean catalog and everyone runs. Everyone runs. The only things I run away from are my intimacy issues and my desk if there’s free white sugar-based foods in a break room somewhere. (Just kidding; I don’t have intimacy issues, just weird thoughts about monogamy since my parents met and have stayed together since middle school. THANKS A LOT, YOU GUYS. Y’all are gross.) Because I didn’t know beforehand that Boston was such an athletic city, I didn’t anticipate meeting all of these men who are able to bench press me. And these are, like, 6-pack having athletes who travel for work and went to boarding school and know the exact amount of expensive cologne to use (which is one spritz that you spray in front of yourself and then walk through it).
[Side note: the other funny thing about Boston is because everyone here dresses so conservatively, I stick out like a sore thumb in my belly shirts and torn jeans and Doc Martens. Here’s what a Bumble dude had to say about it:
Now, for the last five-ish years, I had a type. I like my men like I like my peanut butter: chunky. I loved a good dad bod. Bellies were my kink. And if you had dark hair and tattoos? Forget it. I was gaga for you. The problem was when I put all of the men I dated into a collage and sent it to my friends, these were their reactions:
“They literally all look the same.” – Sophie
“They literally all look the same.” – Shanaz
“They look like a Pokemon evolution of the same man.” – Olive
A few weeks before I left New York, I had coffee with my friend Rob. “Now this is going to sound shitty of me, but what if all of the guys you dated had the same personalities because they had the same physical characteristics? Maybe you should date outside of your physical type and you’ll find fewer people who don’t treat you kindly.” Now here’s the thing. I date dads. I date guys who look like dads. I’m a slut for a pair of cargo shorts and a fanny pack with a Ziploc bag of Cheerios inside of it. I didn’t want to date outside my physical type. But I did want to date outside the personality type of men I’ve attracted in the past. (And I won't touch upon what exactly those personality types are because I don't speak ill of the dead. ps Happy Halloween)
Now one could argue that someone saying “All of my exes are blonde and dumb” and someone else replying “then stop dating blondes” is a similar scenario. But I decided to go along with Rob’s experiment. What if I dated something a little different than my usual?
My criteria for agreeing to go on a date with a Boston dude is as follows:
Couple those six things with physical attraction and turn me over, I’m done. That’s all you need to go on a date with me. It doesn’t sound very complicated, but it absolutely can be. By a pure stroke of luck, I decided to go on one date with someone last week from Bumble and in the end all I’m gonna say is that I really regretted not packing those toys.
So dating in Boston is fun. Moving on.
I made the fatal mistake of thinking I’d want to do a lot of stuff the first week I was here. I thought I would be homesick and discombobulated (both of which I totally was) and would need to make a lot of plans the evenings of the first week. I tend to get stressed out or sad in new situations and in the past, I’d fill up my schedule to distract myself from the discomfort. What I’ve learned about myself as I’ve gotten older is that I should just give myself a break. Let myself ease into things. Relax. I don’t need to keep myself busy 24/7 (which I am famous for doing).
What I had planned for the first week of my trip was a concert of a band I LOVE and a book signing by this badass feminist author I really respect. I ended up selling the concert tickets very easily (thank god), and stayed in the night of the reading (which was free, so it was all good) because this first week in Boston was exhausting. What I did instead was:
I decided that instead of doing everything at once, I’d make a goal to treat myself to one “big” excursion during the week and one on the weekend. And the best part is I’m doing all of these things on my own and LOVE it. I’ve flaked on a bunch of dates because I realized oh, I actually kind of want to do some of these things by myself. I might be the princess of Boston, but I'm also the QUEEN.
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.