The Five Dates You'll Go On: Downtown & Waterfront

The Five Dates You'll Go On: Downtown & Waterfront

“Let’s meet for drinks sometime.” It’s the death knell of any dating app conversation - a vague invitation that ultimately withers as each side volleys back with indecision. End the “I don’t care, you choose” attrition with our date ideas - uniquely tailored for all the matches you’ll meet in the Boston dating world! 

There’s nothing like summer in the city, so this week, we’re tackling the best date ideas in downtown Boston and the waterfront. From performances to patios, there’s a little something for everyone in the heart of the Hub!


The date: a lover of the classics.

The play: Shakespeare on the Common.

The play’s the thing wherein you’ll catch this cutie’s heart! Pack a picnic (or grab takeout on Tremont Street), bring a blanket and watch the performance under the stars. Admission is free, and lawn chairs are available to rent. This year’s production is Cymbeline, a lesser-known tragedy, and it runs every evening except Mondays through August 4. 

Second date? Laugh a little after the tragedy at Shit-faced Shakespeare or High Hamlet, both inebriated, irreverent takes on the Bard’s classics.


The date: a kid at heart with a competitive edge.

The play: Versus.

Game on! Challenge your date to a tournament of retro games at this nightclub-turned-barcade tucked into a side street in Downtown Crossing. You can play all the nostalgic classics: skee ball, Hoop Fever, and even Mario Kart on the big screen behind the bar! Make it interesting and have the loser treat the winner to post-game nosh, served up on neon Frisbees or in old-school lunch boxes. 

Second date? Keep the competition going to Round 2 with ping pong, giant Jenga and life-sized Battleship at Game On in Fenway.


The date: a cinephile with sophisticated tastes.

The play: Movies by Moonlight at the Boston Harbor Hotel.

Now in its 21st year, the Harbor Hotel’s “Summer in the City” series does outdoor entertainment right! Head to Rowes Wharf to catch a flick each Friday night - get there early to grab a table and a bite before showtime. Appeal to the romantic with Sleepless in Seattle or Ghost, or the adventurous with Indiana Jones, Captain America or Aquaman. The full schedule can be found here.

Second date? Make it a double feature and catch a classic at one of the area’s independent movie theaters, such as Coolidge Corner Theater in Brookline, or Harvard Square’s Brattle Theatre.


The date: an outdoorsy type - in that they love drinking on patios.

The play: The Patios at City Hall Plaza.

Summer is a great time to get outside, but some among us don’t love getting in touch with nature. Enter The Patios, back and better than ever for its second season. Beverage selections include beer and draft cocktails from Wachusett Brewing Company, plus hard seltzer and wine. Curl up with a cutie on a cozy patio swing, challenge them to a round of mini golf, or share a snack from the local food truck rotation. And if your date is a dog lover, stop by for Wag Wednesdays - the most ferocious fauna you’ll find here are adorable puppies!

Second date? Continue your exploration of the great outdoors at another beer garden, perhaps the Owl’s Nest from Night Shift Brewing or Trillium Garden on the Greenway.


The date: a history buff who doesn’t mind hoofing it.

The play: Walk the Freedom Trail.

Let’s be honest. You didn’t pay a speck of attention when your fifth grade field trip took you on a walk through Boston’s historic sites - or maybe you’re new in town and still wrapping your head around the city’s history. Start at the Common and follow the red brick trail as far as you like - it conveniently passes by some fantastic eateries if you need a break (I suggest Modern Pastry for sweets or Green Dragon Tavern for pub food and beer). Pro tip: skip the hokey costumed tour guides and curate your own tour, even if you have to make up random facts along the way.

Second date? Get out of town and keep exploring local history. Plymouth and Salem are just two spots that make for excellent (and educational!) day trips.

Stay tuned for next week, when we’ll be coming back at you with five all-new date ideas! Until then, have fun and happy dating!

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