Fun And Relaxing First Dates In Boston

October 21, 2010 10:07 PM

Photo Credit: Douglas Lucas

Congratulations, you got the date! Now what? Coming up with a fun, creative date is almost as hard as asking for it. But with all this city has to offer, there’s no reason to resort to the old dinner-and-a-movie standby. Here are some suggestions for a fun and relaxed first date.

By Katherine Santiago

boston common Fun And Relaxing First Dates In Boston

Boston Common (Photo by Joe Raedle/Getty Images)

Take a Walk

Boston is a walking city – take advantage! Stroll through the Boston Common and Public Garden. Sit on a bench with a coffee or ice cream cone and people watch while getting to know each other. When you’re ready to move on from the park, walk down Newbury Street and window shop.

Other great walking spots: Arnold Arboretum, The Esplanade, Harvard Square

turtlemanatee Fun And Relaxing First Dates In Boston

Photo Credit: Douglas Lucas

Visit a Museum

There’s no reason to be bored or intimidated by a museum date. Boston has museums that cater to all sorts of interests. Sports fans can visit the Sports Museum at TD Garden. History buffs have the U.S.S Constitution and other historical sites. The Museum of Science, with its interactive exhibits, is entertaining for almost everyone. And of course, there’s the Museum of Fine Arts for art lovers. Check out this site to find a museum by both type and location:



Walk on the Wild Side

If both you and your date are animal lovers, use that as a starting point and head to the Franklin Park Zoo. Take time to get to know each other as you walk between exhibits. The animals are also great talking points if there’s a lull in the conversation. This also works well at the New England Aquarium. Who doesn’t love those penguins?

cannons Fun And Relaxing First Dates In Boston

(credit: Doug Pensinger/Getty Images)

Catch a Game…just not an obvious one.

No matter the time of year, there’s always a game going on in Boston.  The four major teams – Red Sox, Patriots, Bruins, Celtics – are fun to watch but can be very expensive.  Stay budget friendly, not to mention original, by cheering on one of the less prominent New England teams.  New England Revolution tickets start as low as $20.  Or catch one of Boston’s two professional lacrosse teams, the Boston Cannons and Blazers.  Another fun option is a college football or hockey game.



Play a Game

Instead of watching a game, play one! Cornwall’s in Kenmore Square has a variety of board and card games for anyone to play. Among the selections are Chutes and Ladders, The Game of Life, Sorry and Uno. Once you get tired of board games, you can move on to one of the pool tables or dart boards. Have fun showing off your charmingly competitive (NOT raging and crazy) sides.

Read: Best Game Nights

tapas Fun And Relaxing First Dates In Boston

File image (credit: Jasper Juinen/Getty Images) )


Have Brunch

Brunch is more casual than dinner, which could help with those first date jitters. There are also tons of options. A quick internet search pops up hundreds of brunch locations, ranging from affordable diners to upscale restaurants. Plus, the earlier time frame keeps things flexible – you can leave and enjoy your day if there’s no connection, or continue the date if you really hit it off.

Prudential Center


Be a Tourist

Sure, it may sound cheesy, but visiting a tourist attraction could be a new experience for you or your date.  It seems that so many people just don’t take time to see the sites in their hometowns. So see the city the way visitors do.  Take a Duck Tour.  Walk the Freedom Trail.  Go to the Skywalk at Prudential Tower.  There are lots of things to see, so get going!

bowling thinkstock Fun And Relaxing First Dates In Boston

Photo Credit: Thinkstock

Strikes to Spare

Bowling is lots of fun and a great date. For a twist, try candlepin bowling, which is believed to have been created right here in Massachusetts. Some rules are a bit different but just like standard bowling, the goal is to knock down all the pins. Unfortunately, there’s no escaping the hideous bowling shoes.

Read: Best Bowling In Boston



Skip Dinner…

And go straight for dessert! Meeting up for pastries and coffee removes the pressure of being on a formal dinner date. Try the famous Mike’s Pastry in the North End for authentic Italian desserts. Another great spot is the Cupcake Shop Sweet, which serves daily and seasonal homemade cupcakes (the Red Velvet is superb!). For a sit-down dessert experience, try Finale. Dessert is the main focus here and their sampler lets you learn each other’s tastes while you learn about each other.

Katherine Santiago is a News Apprentice with WBZ-TV and enjoys writing about her love of Boston area nightlife.