5 Recommendations on how to meet women in Boston, MA!

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5 Recommendations on how to meet women in Boston, MA!

Loaded with deep history, proud folks, and an unique night life, I'm honored to call Boston my home town. As a veteran of the dating scene, I've shelled out $20 covers in the Theatre District and shared a six-pack for free along the Charles River. I've seen men drunkenly stammer through worn out pickup lines while others do marvels with a simple "Hello". Taking into account all my experience, here are five pointers for meeting more women in the city:

Dress to impress. Boston is consistently ranked as one of the worst-dressed cities for guys and it definitely shows. The bars are loaded with goofy tee shirts, Ed Hardy gear, and tattered baseball caps. Stay clear of being a cliché and stick out.
Throw on a fitted button-down shirt, slim jeans, a good pair of dress shoes, or even a blazer/tie-- it makes a huge difference. Women ended up being friendlier and more interested the moment I started dressing better.

Arrive early. Boston isn't the all-night celebration scene like New York City or Chicago, hot spots warm up by 10:00 and cool down around 1:30-- leaving you a short window to meet the ladies. Most of the eligible bachelorettes find a guy early on, so don't wait till the end of the night to approach her. You're less likely to prosper when she's all partied out and unable to remember you. A lot of college girls need to get to the T before 1:00, so use your time carefully!
Don't forget about the daytime. Tourists swarm Boston all the time because of its awesome walkability, but as a local, are you making the most of it? Conserve that beer money and take a walk down Newbury Street, through Harvard Square, or around the Boston Commons. You'll be shocked at the number of hot and responsive single girls there are on a given afternoon.
Don't hesitate to strike up a discussion with a lady reading on a bench or enjoying a street performer in the square. Shops like Starbucks, Espresso Royale, or the Prudential Mall are exceptional spots also.

Know your atmosphere. Boston is a city with various styles and scenes, so it's crucial to find a place that matches your tastes. Here are some basics:

If you like a sports bars....

Cask 'N Flagon

The closest you can get to Fenway without being in it, Cask 'n Flagon is a Boston sports institution. The roar of the crowd is ever-present and the hustle and bustle of fans shuffling down Lansdowne Street can sometimes be just as interesting as the game. You can feel the pulse of the stadium from your barstool. Watch the game from one of their 60 TVs while noshing on pub grub, like pizza, pasta, and BBQ. And keep your eyes out -- if someone blasts one over the Green Monster, it may just land outside.

Tony C's

Named to honor Revere native and Red Sox legend Tony Conigliaro, Tony C’s is a spacious restaurant and sports bar that almost feels like the size of a small stadium itself. The youngest person to lead the league in home runs, Conigliaro played an integral role in the Sox’s famous “Impossible Dream” season of 1967 before being plagued with unfortunate injuries. Over time, his legacy became a career of perseverance and bravery. Now his name shines in neon at four different locations.


Tucked away on the second floor of the Copley Marriott, Champions bar wraps around in a semicircle, and its 36 strategically placed 46-inch TVs give fans a perfect panoramic view of every game being televised. The ceilings reach toward the sky providing a roomy atmosphere while a friendly mix of hotel guests and locals converge for their nearly 40 drafts drafts (including some local microbrews), a wall of liquor, and spirited conversation between fans of all kinds. Soup, sliders, nachos, burgers, and six different flavors of wings round out a menu that will satisfy anyone’s game day diet.

The Fours

There are plenty of bars to pick from on the streets surrounding the home of the Celtics and Bruins, but The Fours is our favorite. With two floors decked out in brick, wood, and leather, the walls are heavily adorned with sports memorabilia. From framed jerseys and famous photos to autographed baseballs, The Fours celebrates Boston sports’ past and present like no place in town. The lengthy food menu offers just about everything you can imagine and its burgers and sandwiches are named after famous area athletes. This place fills up quickly and early if there’s a home game, so plan ahead. Come see why Sports Illustrated once called this place “America’s #1 Sports Bar.” That may be a stretch, but it’s still pretty great.

Parlor Sports

For the more discerning sports buff, there is nowhere more gracious than Parlor Sports. Located at the Cambridge and Somerville town line, Parlor is smaller than your typical Boston sports bar, but if there’s a game on, it’s on here. Parlor opens early on weekends and otherwise at 6pm -- but if there’s a big morning match brewing, you can be assured the bar will open up even earlier. Serving upscale comfort food, craft beers, and even classic cocktails, the staff is sports-smart and friendly. A drop-down boxing mic falls from the ceiling if a bartender wants to make an announcement, and an antique boxing bell often gets rung if something epic goes down. Even on off nights, Parlor finds ways to intrigue its customers with other games of chance, like its spirited and irreverent viewings of The Bachelor.

If you like live music:

Brighton Music Hall

This mid-size Allston venue includes a big stage with plenty of standing room and some seating around the exterior. (There are also seats towards the front, but you could lose out on prime viewing that close). The back room has pool tables—an entertaining diversion in between bands. Expect well-known artists in all genres—from roots rock band like The Blasters, to the insouciant pop of St. Etienne, to the industrial goth artist Ohgr.

Midway Cafe

Earplugs and a rebellious attitude come in handy at this divey veteran bar and music venue located in Jamaica Plain. The Midway hosts local artists of the punk and rock persuasions, as well as cult indie touring bands. Booking is pro-LGBTQ, and queer-friendly bands are regularly featured. Otherwise, attendees might be treated to local legends like Thalia Zedek (of Come) or experimental noize merchants Sool.

Paradise Rock Club

Everyone from U2 to Kings of Leon have graced the Paradise’s stage at one time or another. This mid-size venue is a local rock landmark and has been a part of the city’s music fabric since the '70s—even with its often difficult stage viewing. In addition to worldwide acts, local bands still often make up the bill. Entrance is through the Paradise Lounge on Comm Ave, which serves drinks and a bar menu, and is open on most concert nights one hour before the club opens.

The Middle East

What started as a simple Middle Eastern restaurant in 1970, this Central Square spot expanded in the late 1980s and pioneered the burgeoning local alt rock scene, becoming a major tour stop for many groups. This address comprises several smaller venues for live performances, including the Upstairs, larger Downstairs (the site of a former bowling alley), Zuzu, which hosts experimental artists and the stellar Soulelujah DJs, and The Corner, where musicians play for tips and belly dancers perform. Everyone from Chris Cornell to Jaden Smith, and even Ryan Gosling, have trod these hallowed bohemian boards.

O'Brien's Pub

This small, no-nonsense all-black bar and club offers plenty of room to pile in and still have a good view of the corner stage. It’s a local favorite with a big, long bar on one side and some seating to give guests a bit of comfort during longer sets (or sips, for those only grabbing drinks). Sharing booking with Great Scott, this place has both local bands and visiting, out-of-towners play; it might be punk rock one night, and psych-folk the next.

Rather Country?

Loretta's Last Call

Boston isn’t well-stocked with country music venues, and Loretta’s is probably the closest you’ll get to a honky tonk vibe. Despite being overtly themed, it feels almost as genuine as many of the newer joints you'll find down in Nashville. Sure, it’s no Bluebird Café, but some talented local musicians still play the large stage. Look out for the unexpected national country act now and again, and the bluegrass brunches are a fun hootenanny on the weekends. Moonshine Bellini in hand, you’re soon in high lonesome land.

If you like an indie crowd:


Bukowski Tavern

And Smile, damn it! It's the most universal thing you can do to improve your odds with women. Everybody is aiming to have a good time and you want to show that you're an awesome guy from the start. An authentic smile is ten times more appealing than a stern or blank face.