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Where (and how) to meet women in Boston

Posted by Karyn Polewaczyk  October 2, 2013 02:30 PM

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Last week, I shared my list of places where I’ve consistently met guys around Boston—and the response was overwhelming. The post itself received tens of thousands of page views in just a few short days, and I received a number of emails and tweets thanking me for putting it out there, as well as inquiries from men curious where they, too, can meet ladies about town.

Answering a question like that presents its challenges; namely, that I’m not a guy looking to meet chicks. Luckily, I was able to enlist the help of someone who’s literally made it his business to help guys meet women.

Gentlemen, meet Ben of Kickass Academy.

Ben and I talked about not just where men can meet women, but how—because as I pointed out in my post, the opportunities to meet people in the Hub are pretty much limitless if you’re willing to look beyond the allure of a dark bar. We also discussed what it takes to meet people during the day; why good grooming is not just for the ladies; and how anyone—seriously, anyone—can become attractive.

Intrigued? Keep reading. You’ll also find a specially curated list of where to meet women around town, compliments of my guy friends who do it well (and whom I’d like to thank, again, for sharing their input).

Why don’t we start with what Kickass Academy is all about.

Basically, we offer men’s self-improvement, with a focus on happiness and fulfillment. We spend about 90% of our time talking about how to meet women because that’s where guys often feel they want to go from average to rockstar good. The goal overall is to help guys feel happy, fulfilled and confident, like their lives are in their control. We cover fitness and career, but 90% of our time is spent helping guys get better with girls.

And you say this can be learned?



Kickass Academy started as something I did for myself. I wasn’t good with girls. I wasn’t good with people. I was sarcastic and shy. I had girlfriends, but you’d look at me and say I was an average guy. If someone challenged me to talk to an attractive girl I was terrified. At one point, I read Neil Strauss’s book, The Game, and while I didn’t love all of it, it was the first time I realized that you can learn to be better with girls. You can learn to be the person you want to be. That put me down a several-year path of self-improvement. It wasn’t until about nine months ago that I realized I should start writing about it. Charlie and I started with free content; once we saw that it was resonating with people, and that they liked it, we went with it full-time. Now we’ve got the blog, we’ve got videos, we’ve got premium products.

One of the things that sold me about Kickass Academy is that you teach guys how to approach women during the day. I love that. It almost seems like it’s a better option than meeting people at night, when liquid courage can get in the way.

What's great about meeting people during the day is that you can talk to literally anyone—anyone you find attractive, you can start a conversation with. If people are hesitant to approach others during the day, it's because they don''t know what to say—and that's the first thing we do: provide simple framework for how to start a conversation, so that you can approach someone anywhere, at any time of the day.

It makes a lot of sense. And yet it's so rare to see someone do that. It definitely makes a guy stand out.

The other great thing about approaching people during the day is that you're a big fish in a small pond. People aren't used to it; that's why it works well. You get to have genuine conversations because you're not talking to someone who's expecting to be hit on 100 times. There can be some beginner mistakes—catcalling is one, going right for the phone number is other—but the technique can be learned. We credit everything back to a guy named Soul who lives in London.

So, for example: if you see someone attractive, you first acknowledge the situation [the approach] is random. You say whatever it is you're drawn to; you compliment. Instead of saying, "Let's go out sometime," you say something like "I'd be kicking myself all day if I didn't find out more about you." We know guys who've done it and go on a date right from there. Women remember these things. It's a very easy way to make someone's day.

I don't troll the streets for five hours looking for a date. I live my life; then, any time I see a beautiful girl who I think I'd like to get to know, I just go talk to her. It becomes habit, something you do every day of your life. And it takes five minutes.

Another thing you've mentioned is that you think every person can become attractive.

People sometimes say that looks don't matter. But looks do matter. It's genetics that don't matter. You don't have to play the hand you were dealt at birth. You have to take care of yourself—eat right, adapt a personal style, have interests—because you are your own product. I've been on Accutane, I had braces, I wear contact lenses. That's just what you've got to do. It's attractive to show you can take care of yourself. Attraction isn't just looks. Women tend to be less shallow about it than men; in fact, I just interviewed a female pickup artist who's amazing, and she had a lot to offer on the subject. Attraction is how you carry yourself—you can learn to be fun and someone people want to be around.

What about a guy who says he's shy or he's too old or that he just can't?

They're excuses to not work on yourself. What's more important than say, your age, is how you feel about your age. We've seen people from all starting points get good at this. You can't expect to learn everything in one day, so don't put pressure on yourself.

I know you’re currently living in Brazil, but you’re from the East Coast—you know how brutal dating can be here.

I think the thing in the United States, particularly in New York City and Boston, is that right away, you have to get her to want to know you better. It’s about body language and the approach. In the Northeast in particular, people are a bit more closed off. I think guys take it too personally when a girl doesn't want to give them the time of day, but you have to show why you're worth her time.

That said, let's talk about rejection. I think it's a critical part of dating for a number of reasons, and you agree. You're a good-looking guy—I'm sure there are people who might think, "Well of course he's okay with it, he's attractive." But you say that the same rules apply for good-looking guys.

You probably won't find anyone who's been rejected more than me. We all started off with poor habits; that's how you get good. I love rejection. It's an awesome feedback mechanism. When people are wounded by it, well, the person who rejects you doesn't know anything about you. They just know how you presented yourself. So when I am rejected, I ask: how did I just present myself? What did I do to make the person not want to talk to me? Rejection isn't your internal identity. At our Rio Academy, we have a student whose homework it is to go out tonight and get rejected a certain number of times.

This is a loaded question, but I'll ask it anyway: what can a guy do if he wants to get better with women?

Ah, the "How to get better with girls" question. Everyone wants to get good, fast. It's like we talked about: you've got to adapt a learner's mindset, the same way you would a new language or sport. I think you've also got to find someone who teaches it. It doesn't have to be us, but you've got to find someone who knows what they're doing. You can go out and talk to a million people, but you've got to have framework in place. Start basic. Work on yourself. Read books. Learn how to be good around people. You've got to practice, push yourself outside of your comfort zone. It's when you try things (and fail), you learn from it. Set smart goals within your control. The best results are when people don't try to turn it on and off. Don't try to flip a switch. Be confident and happy all the time, every minute of the day. When they happen upon someone they want to meet, it becomes natural.

Kickass Academy will make a stop in Boston this November; seminar dates and times are TBD. To learn more about Kickass Academy, visit their site and follow them on Twitter. You can also reach Ben via email at

Now that you've got some tips on how to meet women, here's where you'll find them.

From a friend who works in finance (age 33, lives in Beacon Hill):

Carrie Nation ("What better way to establish alpha male status than by sinking the 8 ball in your friend's face to take the game?")
Towne ("Has a unique feel to it; I've met some very attractive women here")
Drink ("Inhibitions go down with whatever the mixologists there come up with")
Lucky's ("Talent to be spotted, music to listen to")
Atwood's Tavern ("Worse case scenario, the music scene is strong and you can Uber your way back to civilization if things don't work out")

From a friend who works in real estate development (age 33, lives in Charlestown):

"I think part of meeting the right person starts from within. I hope that doesn't sound too Zen, but I truly believe that will help you attract a better girl. That said, I've always found that doing everyday things—grocery shopping, working out, running errands, walking to and from lunch—offers the best opportunity to strike up conversations with quality chicks."

From a friend who works in career coaching (age 28, lives in the North End):

"The Shambhala meditation center in Brookline is great. They offer a session for people under 30 on Tuesday nights and I was shocked at how many pretty women were there when I went, all of them intelligent, thoughtful, and self-empowered. Also, I'm a member of an alumni entrepreneurial club, full of ambitious, creative people who want to connect."

From a friend who works in the arts (age 35, lives in Davis Square):

"The arts are full of ladies. Not that I pursued a career in music as a way to meet women (I swear) but I've certainly observed the odds are in the favor of straight men at the ballet, opera, symphony and museums. Young professionals' arts events I go to are about 70% women, 20% gay men, 10% straight men (most of whom are taken). That means if you're a single, straight man, you've got the the odds considerably stacked in your favor. It also offers a great chance to get the conversation going, since you're in an interesting arena."

From a friend who works in the wine industry (age 35, ex-Bostonian who lives in Brooklyn):

"Silvertone is great because the bar is small but cozy with tons of regulars. It's also very social and reasonably-priced, so if you meet someone and want to stay out longer than expected, you can, without breaking the bank. The vibe in the North End is more communal and outgoing. Stick to smaller wine bars. I'm a fan of Vinoteca di Monica. And Toro. Toro is like the zip-line of the Boston scene."

Ben also tapped his Boston network to see what they had to say:

•The Liberty Hotel ("You'll definitely see beauties here—it's a smokeshow market—and attracts an older crowd. A killer spot on Thursdays, Fridays and Saturdays")
The Brahmin ("Best on Fridays and Saturdays")
Tia's ("People are definitely there to meet and mingle")
The Burren ("Has a hookup culture")
Saloon ("Cool date spot")
•The Charles River Esplanade ("Awesome for approaching girls during the day")

This blog is not written or edited by or the Boston Globe.
The author is solely responsible for the content.

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About this blog

Karyn Polewaczyk lives and writes in Boston, and believes that heading out into that good night, like any adventure, begins with the first step. Let's Go Out is a conversation about dating and nightlife in our notoriously chilly city, with first-hand tips from the trenches. Karyn's writing, which focuses largely on women's lifestyle topics, has appeared in the Weekly Dig, Jezebel, xoJane, Northshore Magazine and, among others. Follow her on Twitter at @KarynPolewaczyk.

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