And that’s a wrap on Boston.
My first leg of the trip was pretty much everything I wanted it to be. It challenged me in so many ways, I really got a good understanding of what my life in Boston would be like if I settled here, and I relearned how good I am at taking care of myself and enjoying time on my own. Have you ever seen someone in NYC with headphones on singing and dancing while waiting for the train or at a crosswalk? And you’re like that person is living their life not giving a single, solitary shit what anyone around them is thinking of them?
I danced and sang to myself so many times with headphones on around Boston. I was that bitch. I have never felt so calm and peaceful and just fucking GIDDY in my entire life.
The first two days I was here, feeling scared and sad and FRUSTRATED THAT BOSTON’S STREETS WERE MADE BY FUCKIN’ HORSES AND AREN’T A GRID, all I did was keep questioning whether I had done the right thing. I missed the support system of friends and family I had built in New York. I have never traveled to a new US city barely knowing anything or anyone; I’ve lived in New York my entire life. I also hadn’t dated in a year and a half. I sincerely wondered if I could financially afford to eat the non-refundable deposit I had put on my apartment in Brookline. In short, my first 48 hours in Boston were spent wondering if I was strong enough to do this trip. After all, Boston was me dipping my toe into this year-long adventure. If I couldn’t survive these 7 weeks, how the fuck would I be able to do close to a year away from home? Who did I think I am?
All of these feelings quickly passed after I took my psych meds, ate a sandwich at Cutty’s, and got laid.
You know what happened after those 48 torturous hours that turned my whole life around? I started owning my fucking life. “I am doing this for me,” I reminded to myself. Not for anyone else. There were suddenly no rules. So what did I want to do? In Boston, owning my life meant:
And when you own your own life, you start owning other stuff, too. These are some things I have done that I didn’t give myself nearly enough credit for until I did this trip:
Tracee Ellis Ross gave a talk to Glamour magazine (that everyone should watch in its entirety here) about living your life intuitively as a woman. She says:
“When we put ourselves first by doing things like saying no, speaking up, sleeping with who we want, eating what our bodies intuitively tell us to eat, wearing training bras instead of pushup bras, posting a picture of ourselves without using FaceTune, we are condemned for thinking for ourselves, being ourselves, for owning our experiences, our bodies and our lives. That kind of boldness is seen as threatening and scary. What would it look like for women to completely own our power? To have agency over our own glory, our sexuality, and not in order to create a product or sell it or to feel worthy of love or use it as a tool for safety. But instead, as a way of being. Imagine that. Truly owning our own power, agency, and sexuality.”
This trip started off as a way to make sure that I wasn’t going to settle down in NYC for another 11 years without knowing what other cities are like, but what it ultimately taught me was to own my power.
[I want to take a second here to shout out my day job—I know some of my coworkers read my blog and this trip would NOT be possible even in the slightest without the stability, flexibility, and unending kindness of everyone on my team. Thank you, thank you, thank you.]
So yeah. This trip has been really amazing for me. Here are some of my favorite Boston memories:
And to think that this is just the first leg of my trip! I am truly #blessed.
Before I get into some AirBNB tips, let me tell you a little bit about where I had been staying for the last 7 weeks. My AirBNB sublet was so weird in the absolute best ways. Now, I lived in Brookline Village and really wanted to live with people during this first excursion because I felt weird being on my own in a city I didn’t know. It was expensive as fuck, but ultimately worth the money because it was very quiet during the day, incredibly safe, and very convenient to everything. I don’t think I would have liked living in any other part of the city, to be honest.
I had three roommates:
Anyway. Here are some hot AirBNB tips:
On a very personal note—after my ruptured cyst, I learned that my autoimmune disease, which was very stable for the last two years, has suddenly become not-so-stable again. The next six weeks home in NY will be filled with doctor’s appointments, tests, and seeing if I will be healthy enough to continue the trip in January if I don’t need to go through treatment again. If I have to put things on hold or renegotiate the timeline of my trip, I will make peace with that. In the meantime, I will always cherish my time in Boston. Here are some things I learned:
First city down, 5 more to go. Thanks for everything, Boston.
My friends have been asking if I could write a post devoted to whether the sex and dating in Boston is better than it is in NYC. So this post is gonna be that post. If you’re someone who doesn’t want to hear about that stuff, we’ll be back to our regularly scheduled programming next week. Sit this one out.
If you’re still with me, the short answer is yes. It’s so much better.
Now here’s the thing. The recovery from my ruptured cyst is long (6-8 weeks!) and frustrating and I try really, really hard to let it not slow me down. I have an autoimmune disease so I’m well-versed in feeling like crap often and yet not letting it prevent me from doing the things I want to do, to try to live my life with some semblance of normalcy. So I’ve continued to go on dates and explore and do things the best that I can. You don’t know humility until you’ve gone on a date with a disposable heating pad affixed to the inside of your underwear. The thing that has motivated me to meet up with people even when I’ve been feeling poorly is, well, how hot the dudes who ask me out are. For example:
Now, I have really pretty eyes and skin and hair, as well as perfect boobs and an ass that doesn’t quit, but I’m also self-aware enough to know I’m not a ten. I mean, *I* think I’m a ten because I like myself, but by society’s standards, I’m not a ten. I have a weird chin that dimples when I smile, a belly and cellulite and scraggly bottom teeth (top row are fine, but I did that thing as a teenager where I kept breaking my retainer on purpose because I didn’t feel like wearing it and now I have jacked up bottom teeth). I can’t rate myself because rating yourself is bullshit, so I have no idea what number I actually am. And to be honest, I don't really fucking care.
The men who have been asking me out, on the other hand, are all tens. All of them.
Now I don’t share the likenesses or names people I date in my writing, but of course I send pictures of people to my friends like any other single person. Plus, I’m in a new city and I always share my location and first and last names of people I hook up with with my close friends because it’s the safe thing to do. These are some snippets from conversations with my favorite NYC buds:
My personal favorite:
Boston men, in comparison to NYC men, are:
But here’s the thing. Just because they’re all beautiful doesn’t mean they’re all perfect. Boston ain’t all sunshine and big dicks. I’ve still had to deal with dishonesty, evasiveness, flakiness, emotional manipulation—all the things you encounter when you date anywhere. The other frustrating thing about Boston that I didn’t realize is that many people live here, but don’t really work here. They travel to cities that are bigger hubs of commerce very frequently and Boston is just their home base. Three-quarters of the guys I’ve gone out with aren’t home often—which is great because I like being left alone and doing things on my own, but also frustrating when I do want to meet up with someone again. Many of them want virtual girlfriends that they can hit up when they’re bored and horny in a hotel room, which is great for them, but not for me when the purpose of me traveling is to go out and meet actual people IRL and not stay inside texting. It’s like, I just sent you a Snapchat of me spitting on my tits and you aren’t able to get together? Like, how dare you.
Anyway, the worst experience I had in Boston was when a guy came over and mid-hookup I realized he had a crippling case of BDS. BDS (Big Dick Syndrome) affects roughly a quarter of the male population. Symptoms include not knowing where the clitoris is, thinking a girl can get off from giving head, and genuine shock when I tell them only 25% of women can orgasm from penetration alone. BDS destroys communities everywhere and Boston is no different. This guy had the biggest dick I’ve ever seen in my life, dethroning the last record holder, which ironically enough, was the guy I lost my virginity to at 17 (cue me having unrealistic expectations regarding penis size for YEARS).
Anyway, Big Ol’ Donkey Dick and I are hooking up and it's dawning on me that I'm doing a lot of things to him and not getting anything in return. I ask him to do some things (and it’s not anything crazy! Just basic stuff like “kiss my neck”) and he'll do it for .5 seconds and then stop so that the attention was back on him. Even cuddling, I like to touch my partner actively (caressing, massaging) and he was just lying there, not really touching me back. I ended up turning to him and saying “Do you want to know what I think when it comes to you?” He says yes, so I say, “I think you’re interested in getting taken care of and that’s it.” He asks if I think he's selfish in bed. I say yes. He laughs before saying, “I like attention.” I say I like attention, too. Then I flat out say, “You don’t care about my pleasure” and tell him it was probably best that he left.
One of my favorite drag queens, Katya (real name: Brian) made an absolutely brilliant video recently about toxic masculinity and sex that everyone should watch. In it, he says, “People get disappointed when you won’t go where they want to go. If that’s the case, then you’re just jerking off on another human body. And guess what? There is a whole universe of porn out there for your perusal, okay? If you can’t get your nut in a compassionate way, flip on the screen, mama, and support the fucking actors who are paid to give you pleasure.”
I couldn’t support that sentiment more. If you’re not excited about getting your partner off, all you’re doing is masturbating with another human body. That’s the whole difference between masturbation and sex—with sex, you have to actually care about the other person’s pleasure. You need to make sure they’re taken care of. If you don’t, then you shouldn’t be having sex. End of story.
So anyway, I had a sick feeling in my gut right up until I told DD my thoughts, but the moment he left, I felt a huge flush of relief. I called my friend Dave to ask if I had done the right thing, if I was too mean (ah, the curse of being a woman and feeling the need to constantly apologize) and he said, “In the eternal words of early 2000s MTV’s hit show “Next": NEXT!”
There have been a few other ridiculous things that have been said to me during Boston hookups (I’m gonna use generic white dude names in the rest of this post and not the actual names of my hookups, obviously):
“Maybe you’re desensitized because you use a lot of toys.”
Maybe I’m having a hard time coming because you put on Amy Winehouse to fuck to, GREG.” (WHO THE FUCK FUCKS TO AMY WINEHOUSE) (AND DESENSITIZATION ISN'T A THING; IT'S BEEN PROVEN SO MANY TIMES)
[I asked him to grab my hip] “I figured you wouldn’t want me to get rough with you because you asked me to kiss you gently.”
Yeah, well, your tongue was in dagger territory and I don’t think anyone wants a tongue aggressively in their mouth.
Lastly, here’s how to know if your partner watches a lot of porn: he calls you "baby" during your first hookup, catches himself, asks if it's weird that he just did that and YES IT IS, MARC, BUT I CAN’T TELL YOU BECAUSE IT’LL RUIN THE VIBE.
So that’s been the dumb stuff. Here's a roundup of the really, really nice stuff that's been said to me:
“Your body is perfect.” (I’ve had this said to me twice, actually, and ughhhh it’s so cute!)
“I love your nipples.” (You can thank Dr. Douglas Roth of Mt. Kisco, NY, for that.)
"Your tits really are perfect!" I don't lie to people, KEVIN.
“You’re SO soft. Like, when you’re not busy, do you just constantly moisturize?” (I died laughing at this. And then I texted my friend who gave me SUCH shit for asking for a certain moisturizer for Christmas that when she gave it to me, she said, “What kinda cocoa butter-ass bullshit did you make me buy you?” THIS IS WHY, CHELSEA. THIS IS WHY.)
“You really understand the rhythm and speed of giving head." (My reaction.)
"It's pretty fucking obvious that you're amazing at sex." (My reaction.)
So that’s Boston. Sometimes you have the best sex of your life and sometimes you have to kick a guy out and sage your apartment. Namaste.
The ruptured ovarian cyst kinda threw off my trip a little (and I didn't realize recovery is 6 to 8 WEEKS gahhhhh), so I'm behind on blogging, but I hope this long post filled with pictures makes up for it.
I spent 2 weeks in bed pretty much like this every day:
I've tried to make sure the medical crap hasn't completely derailed my trip or prevented me from doing things I've wanted to do, so I try to remain flexible (taking a cab when I'm in too much pain to walk, etc). Here's what I've been up to:
Goddamn. This place is incredible. The first time I went there, I got the roast beef sandwich, which has onion straws and some sort of sauce that is Jesus’s sweat; it is an otherworldly experience. I also tried the house-made potato chips (pretty good) and limeade (AMAZING). The next time, I got a vegetarian sandwich (broccoli rabe, provolone, and tomato jam on a pressed sesame seed roll) and a tomato soup. Then I packed the pork/fennel and the pork/broccoli rabe (these two sandwiches are only served on Saturdays) for a picnic with one of my friends. “Gee, Dana, it seems like you go here a lot,” you might be wondering. Yes. Yes, I do. This place is so orgasm-worthy, it should be listed under the “Fuck” section instead of the “Eat” section.
I had a slice, which was pretty good! Was it worth the wait? I’m not sure, but the point of this trip is see what everything is like, right? What I liked most about Galleria Umberto were the prices—I ordered one slice and a ginger ale and my bill was three bucks and change.
Mike's has the only lobster tail I’ll ever eat since I don’t eat seafood (BUT YOU'RE IN NEW ENGLAND; I know, I know... I’m a demon). It was amazing. Super crunchy and chewy in all the right ways and the cream was perfectly vanilla and sweet (not too sweet). The lady asked if I wanted powdered sugar on top and I was like “Girl, yes. Let’s do this.”
I order takeout from here all the time, especially during the weeks I’ve been on bed rest. I’ve gotten the turkey reuben, sour pickles (fucking amazing), chicken matzo ball soup (DITTO), this sampler that had a piece of cinnamon kuegel, meat pastry, cheese blintz with berries, and a potato pancake with sour cream and applesauce (so legit). I might have eaten that entire sampler after getting out of the ER because I wasn’t allowed to eat at all during the entire day.
I heard from so many people that I had to go here, so I tried it out. I got a chicken burrito and horchata and then did that thing where I was still hungry, waited on line again and got an order of guac and chips. And I’m glad I did because it was the best guac of my life and the CHIPS WERE WARM, which is the equivalent of someone talking dirty to me.
So fun! Great people-watching. Went on a date here and we shared nachos, a pork tamale, a carnitas burrito and spicy chicken tacos. I had a few bites of everything (we agreed the burrito was the best), a horchata, and a frozen margarita (which was strong to me, but I’m a total lightweight and pretty much never drink unless I’m eating Mexican food, so who knows if it was actually strong).
Best falafel I've ever eaten. Better than anything I've had in NYC and that's saying something.
I got one scoop of “Cookies ‘n’ Cake Batter,” which was so-so, and one scoop of rum raisin because I am ten thousand years old and it was fucking delightful.
Lamb roti, papaya salad, fried ribs (*I would recommend these), coconut sticky rice (*I’d recommend this, too), chocolate cardamom panna cotta. The bartenders are super lovely. I had a mocktail that was essentially a ginger-y lime rickey. The bartenders knew the person I was with and I were on a date so at the end of the meal, they made me a little frozen coconut-y non-alcoholic drink with a flower in it and gave my date some sort of aperitif, which was charming as FUCK.
It’s just been such beautiful weather here, so one day I walked from the North End to the Lawn on D, which was amazing. It’s about a 45-minute walk and the lawn was miraculously not busy, so I just put on my headphones, relaxed on a swing for a few hours, listened to some classical music in the sunshine and just let my mind feel empty and enjoy the moment.
I went to the symphony at Harvard and every time I go to Cambridge, I almost always get off the T at Hynes Convention Center and then just walk across the Harvard Bridge. It takes about an hour to walk from the bridge to Harvard campus and I probably shouldn't do it as often as I do because #ovaryproblems, but COME ON. LOOK AT THIS VIEW. How could I not?
A lady never tells about her conquests.
Who the fuck am I kidding.
I’ve slept with a few people while I’ve been here. (Safely, of course, and with emphatic consent.) One is an athlete (he’s a fighter) who picked me up BY THE BACK OF MY THIGHS in a very Josh Groban-like manner like it was nothing. We’ve been on a couple dates (including the symphony at Harvard, where we proceeded to get stoned out of our minds (it’s legal here) and I cried during Leonard Berstein's "Somewhere" because it reminded me of my mom and how much I miss her and thank GOD my date didn’t see because it was super embarrassing); he is lovely.
Then I went on a coffee/tea date after work one day with a former Marine with the most hypnotic eyes I’ve ever seen (and a jawline/cheekbones that make his face have more structure than my entire life); we were talking very openly (read: not creepily) about body positivity and sex positivity, so I told him about the athlete picking me up by my thighs and he goes “Well, I can do that, too.” And so later that night he proved that he CAN indeed do that. Thank you for your service, sir. God bless America.
I had a date with someone this past Thursday who works in a psych ward—he provides support to acutely suicidal patients who are often severely eating disordered. He wants to ultimately receive his PhD and do deep trauma therapy. I told him about the CBT therapy during eating disorder recovery I did ten years ago (and how I still practice mindfulness to remain symptom-free), the exposure therapy for PTSD I just completed this past spring, and how I understand the importance of the work he does and wants to do. We also played my favorite party game, "Which One of Us Has a More Fucked Up Past?" (he won) and my second favorite party game, "Which One of Us Has Been on More Psych Meds in our Teens?" (I won that one). Our conversation was incredibly engaging and enjoyable. He, too, is lovely.
[Y'all, I've been really lucking out on who I've agreed to meet up with IRL from dating apps. Everyone has been deeply kind, intelligent, open, and respectful. Some cosmic force has been blessing me.]
Lastly, I’ve been to one lingerie shop and a few sex toy stores:
Forty Winks (Cambridge): This lingerie shop reminds me of my favorite shop in NYC (Journelle); I wish the selection was a little larger (it is REALLY small compared to what I’m used to), especially when it comes to the super sexy/boudoir stuff and not everyday bras, but the women working there are lovely and it was a really pleasant shopping experience.
Hubba Hubba (Cambridge): Amazing kink selection if you’re into that stuff. I’m personally not, but I can appreciate the craftsmanship of a latex pink pig gimp mask for $95 when I see one. A lot of hardcore BDSM stuff, costumes/kinkwear, and a fairly sizeable LGBT-friendly section. Prices are pretty fair and the quality of the stuff looks like it’s worth it. I didn’t do a thorough run through of their costumes since I was just browsing, but they seemed pretty inclusive in terms of sizing!
Good Vibrations (multiple locations; I went to the one in Brookline and the one in Cambridge): This place reminds me of my home: Babeland in NYC. They carry much of the same merchandise. They had what I was looking for: Trojan Supra condoms (non-latex) and packets of Sliquid Sassy (horrible name and packaging; best anal lube on the market) and Sliquid Silver (best lube on the market for everything else--penetrative/oral/fingering) that I always keep in my wallet. I also bought an unscented massage candle (that I ended up trying with the fighter; it was okay--it wasn't as high-quality as the Babeland ones) and a postcard that says “Pleasure is your Birthright,” which I LOVE.
I've done a lot of eating, walking, and dating--all mindfully and enjoyably. Boston has been wonderful. I have no regrets about this trip and am so fucking happy.
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.