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Boston Dating: A Guide to Dating in Boston

For a few years now, Boston has been ranked among the best cities in the nation for singles. Boasting the finest in culinary and cultural attractions, this unofficial “capital of New England” has a lot to offer those looking to meet someone special.

Dating in Boston: The Neighborhoods

Boston is “a big little town,” with each of its 21 officially recognized neighborhoods reflecting the culture of the community. For a taste of Italy, stroll down Hanover Street and visit Mike’s Pastry for fresh cannoli. Be greeted by cheery Irish accents at Kitty O’Shea’s and Ned Divine’s located at Faneuil Hall, or experience a hodgepodge of traditions in Jamaica Plain. Boston’s Financial District’s skyscrapers tower over gourmet restaurants, chic shops and well-dressed business people looking to unwind with a cocktail during happy hour.

Dating in Boston: Student Life

There are over 40 colleges in the Boston area, making it a great city for academically minded singles seeking soul mates. Check out college-crowd favorites like the Beacon Hill Pub in Beacon Hill, and the Model Cafe in Allston, near Boston University. Students and non-students alike can turn school events into fantastic dates. Check out symposiums, special lectures, student concerts, theatrical productions and sports games.

Dating in Boston: Food and Nightlife

Phantom Gourmet (and annual Phantom Gourmet Food Festival) keeps everyone plugged in to the best deals in town. Regional cuisine has an emphasis on seafood, so be sure to enjoy the fresh fish at Legal Sea Foods. Or dine on the international offerings at Sonsie.

Boston isn’t known for its late nights — bars here close at 2 am — but that doesn’t mean you can’t find a student-approved pub or significantly swankier nightclub worth frequenting as midnight approaches. Head to Scullers Jazz Club for some of the city’s best jazz, grab a microbrew in the up-and-coming Liberty Wharf area, or transit out to Cambridge’s Club Passim, which helped launch the careers of Joan Baez and Shawn Colvin.

Dating in Boston: Sports

The Celtics, Patriots, Red Sox, or Bruins. Pick your team and join in on the fun in this sports-crazed city. Whether you go to the game or squeeze into a crowded sports bar near Fenway, just be sure to hate the Yankees and you’re sure to have a blast.

Dating in Boston: Relaxation and Fun / Outside

Looking for a low-key afternoon for two? Take full advantage of Boston’s Emerald Necklace, a 1,100-acre chain of nine parks linked by waterways and parkways. People-watch in Boston Common, the U.S.’s oldest public park, or visit Franklin Park Zoo, located in the historic Franklin Park. If you visit the Public Garden, bring your camera; it’s the first public botanical garden in the United States and is filled with bright blooms and unusual plants.

Dating in Boston: The Harbor

For exercise buffs, jog or bike around the Charles River, join the sailboats or rowing crews as they depart from the Boathouse, or take the ferry to a Boston Harbor Island for a quiet date by the water. In the evening, enjoy a view of the skyline while dancing to great music on a “booze cruise” on a Boston Harbor Cruise Ship.

For a hand-in-hand history lesson the beautiful outdoors, Boston’s mile-long Walk to the Sea will lead you from the State House on Beacon Hill through historic landmarks to the sea.

Dating in Boston: The History

Boston is packed with great date ideas for history buffs. Take your date to the Paul Revere House, downtown’s oldest building, or walk the Freedom Trail, where tours, conducted by guides dressed in period costumes, lead you to significant historical sites throughout the city.

Climb the 294 steps to the top of the Bunker Hill Monument at Breed’s Hill. It’s free, as is a tour of the USS Constitution, the oldest commissioned warship still afloat in the world.

Pack a picnic and lounge in Boston Public Library’s courtyard after your free tour of the nation’s oldest public library.

Dating in Boston: The Culture

Looking to appreciate a little culture on your date? The recently renovated Museum of Fine Arts is one of the world’s most comprehensive art museums. Your admission permits a second free admission within 10 days.

Dress up and take your significant other to hear the world-famous Boston Symphony Orchestra or equally famed Boston Pops Orchestra play at Symphony Hall.

Worthy of note: Boston has been influential in the punk scene. So if the orchestra doesn’t appeal to you, your options are not limited.

Not sure who’s in town? Pick up The Phoenix, New England’s arts-and-entertainment listings. You’ll be sure to find a comedy act, local band or gallery night worth seeking out.

Dating in Boston: Seasonal

Season changes here keep things interesting. Summer temperatures can reach 100 and winter can get as cold as 10 degrees. Don’t just hibernate until spring’s arrival. Bundle up and walk through a snowy lit-up Christopher Columbus Park. Love is in the air every spring, but it’s Boston in the fall that earns this city its reputation for beauty. Take a stroll through the colored leaves when summer’s heat gives way to crisp autumn.

Dating in Boston: Celeb Sightings

Boston’s Hollywood connection extends beyond Matt Damon and Ben Affleck. The city is making a name for itself as a film-production hotspot. With your date and a map, scout out famous film locations like Faneuil Hall, the South End, and the Public Gardens, or celebrate Boston with a made-at-home movie night including The Social Network, The Town, The Proposal, The Departed and Mystic River.

Learn more about singles and Boston singles here.