17 Ways Dating in Boston Is Different Than Anywhere Else

Let’s face it, Boston doesn’t exactly have a romantic reputation. Unlike New York or Paris, we’re not known for our glittering parties, scenic strollable avenues, or adorable patisseries. Our charm comes in the form of Nor’easters, questionable accents, and a veering-on-psychotic love of sports. So if you want to find love in Boston (like Gronk erotica-level love), persistence and creativity are key. Here are 17 things you need to know before you head out for that wicked-hot date in the Hub.

Flickr/Thomas Hawk

1. “So, do you go to school around here?”

Boston has a huge student population, so if you look like you're under 40, almost everyone will ask if you’re in college. If you’re not in college, you'll be asked where you went to college, and whether you’re in grad school. If you're not in grad school, the person asking may pause, give a puzzled look, and contemplate their own crippling student debt before continuing the conversation. Just resign yourself to talking about your education every time you go out. 

2. We hit on people in bookstores

Ditto for artisanal ice cream places like Toscanini’s and FoMu. I could try to explain why this is, but I would just be making stuff up. 


3. We don’t go out when the Sox are playing

Or the Pats. Or the Celtics or Bruins, for that matter. Basically, sports games are blackout dates for dating, UNLESS the game IS the date (which is pretty often if we’re honest). And if you know what’s good for you, you won’t go Downtown on Patriot’s Day, or cross the river during the Head of the Charles Regatta unless you’re partaking in the festivities.    

4. We don’t care about fashion

Only a small pool of men bothers with belts and button-downs around here. Women wear flats on coffee dates and almost everywhere else (because cobblestone streets are hell on stilettos). Unlike women in other major metropolitan areas, Boston chicks are typically more concerned with comfort and warmth than with fashion, so there better be a damn good reason to get dolled up. The notable exception to this is Back Bay, where ladies wear lipstick and Lulus to walk their dogs from one end of Newbury St to the other.  

Flickr/Thomas Bonte

5. If it's not on Gcal, it's not a date

Outside of Silicon Valley, Boston is one of the biggest tech cities in the country, so everybody has 9,000 different apps to manage their social lives. If you don’t actually watch your date entering info into their smart phone, don’t expect them to remember it.  

6. We probably met you through a device anyway

Almost everybody is on OkCupid, Tinder, and/or Grindr. Observing OkCupid dates in the wild is practically a Cambridge-side spectator sport. Head to Kendall Square for the best seats.  

7. Everybody’s kind of awkward

Sure, there are awkward people everywhere, but in Boston, it seems like the lion’s share of the dating pool. Accept the inevitability of dating people who spend more time with their MacBooks than their fellow humans, send unsolicited and inaccurate erotic fiction via text message after your first outing together, break out a backgammon board in the middle of a bar but refuse to teach you how to play, or demonstrate how many push-ups they can do (approximately five) in the middle of a crowded Chipotle, while confused onlookers hesitantly order burritos. Not that any of these things have ever happened to me.

Flickr/Ian Britton

8. Living across the river will be a dealbreaker

Most people don't want to date someone who lives too far away, and in Boston, “too far away” usually means the other side of the Charles. One mile away and still in Boston proper? Terrific. One mile away in Harvard Square? Nope.  

9. Roomies are a thing

Most Bostonian 20-somethings (and a fair number of 30-somethings) live with other people their age, so you better have that Spotify playlist on lock, and the dishes out of the sink by morning. On the plus side, this means most of us aren’t going to move in with you until we’re good and ready, and even then, we’ll likely make sure there are a few buffer friends in the house so we can try out the whole living-with-you idea before really shacking up.  

10. Nobody’s here to act or model

Unlike in NYC and LA, the people you date will not have professional headshots on their online profiles. They’re more likely to post selfies of themselves in graphic T’s and enormous, name-brand headphones.  


11. We spend the first 5-10 minutes of every date figuring out where to lock up our bikes

And despite our best efforts, there's always the chance that it'll get stolen and we'll have to Uber home anyway.  

12. We are obsessed with Uber

In winter, Bostonians will take an Uber to get to the T because paying $9 to avoid five minutes of frigid air is totally worth it. In the years before car sharing, we probably would have slept over just to delay the inevitable and horrible trek back to our apartment. But it’s 2015, and we no longer have to sacrifice our standards to avoid hypothermia. 

Flickr/John Hilliard

13. "I know about a free parking lot in that area" is a declaration of love

Because Massholes are everywhere, parking means war, and we won't give up our hard-earned secret parking places to just anybody. Likewise, you’ll know your date really digs you when they offer to help shovel out your car and find a cardboard box to put in its place.  

14. Polyamory is (relatively) common

Polyamory is a much more accepted lifestyle here than elsewhere in the country. In liberal crowds, even non-poly people will get offended if you talk about it like it's a phase.

Flickr/Football Schedule

15. Everyone is in love with Tom Brady

Guaranteed, Brady love transcends age, gender, race, time, and space.

16. If you’re gay, you will end up at Machine

There are a ton of gay and gay-friendly joints around town, but Machine is the black hole of the LGBTQ scene; it’ll suck you in, and before you know it, you’ll be trying to pole dance with the ripped lesbian chick in the trucker hat whose moves are 1,000 times better than yours (just don’t try to Snapchat the experience). You’ll probably also end up at Paradise, Machine’s much trashier Cambridge cousin.

17. We’re pretty kinky

Maybe it’s the years of censorship and sexual repression, but Boston’s doctors, lawyers, students, programmers, and artists are steadily establishing a reputation as some of the most sexually adventurous in the country.

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