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.
Dana Hamilton is a New York City-based writer who has a passion for all things 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, and Thrillist, 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.
Dana Hamilton is a New York City-based writer who has a passion for all things 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, 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.