We get it. Coming up with an original date idea can be more painful than nailing down the date itself. The pressure's on in spring and summer, when it seems everyone's picnicking on a grassy knoll or taking in the oodles of free outdoor events. But for the love of the next outing, don’t just default resort to dinner or drinks. In any season, Boston can surprise with its couple-friendly excursions. We've broken down the very best options below with ideas for every budget, and there's even some for you old “married” types to get in on the action.
Climb some walls (and fall gracefully)
Somerville
You matched thanks to your shared sporty interests, so cut to the chase with a vertical date on the climbing walls of Brooklyn Boulders Somerville (just $32 for a day pass). Afterwards you can head next door for beers and a little live music at Aeronaut Brewing Company.
Dork out over board games
Coolidge Corner & Somerville
It’s normcore for a nominal fee. Knight Moves Cafe calls itself “your living room away from home,” which translates to a den of G-rated pleasures: fair-trade coffee, hot chocolate, and above all, a colossal board game library. (The Brookline location also offers a few foodstuffs like hot dogs and cheese plates.) BYO for a nominal corkage fee if you want to move into PG territory.
Break the ice with drinks and Skeeball
Central Square
A4cade is all about the simple pleasures: ‘80s arcade classics (Galaga, Ms. Pacman), grilled cheese and soft serve from the adjoining Roxy’s Grilled Cheese, and potent cocktails to help get the conversation flowing more freely.
Get tickets for a concert on the waterfront
Seaport
For live music and fresh air, catch a concert at Blue Hills Banks Pavilion. Located in Seaport, the massive tent accommodates thousands of fans of all ages. This summer, Big Sean, Vance Joy, Charlie Puth, Beck, Arcade Fire, Janelle Monae, and O.A.R. will take the stage. Jason Mraz and Brett Dennen are putting on a night of “Good Vibes” in August -- seriously, that’s what the tour is called.
Discover the city's best ramen
Porter Square
These days, everyone’s more impressed by a hole-in-the-wall revelation than the next big opening. And Yume Wo Katare is practically dining theater: the staff shouts “we have a perfect!” if you successfully finish your entire (enormous) bowl of pork ramen (although maybe save that achievement for a later date). The inevitable outside wait just allows more “get to know you” time. For other great ramen joints, check out our updated guide.
Slurp one-buck shucks
Various locations
Are they aphrodisiacs? No, not so much. But the placebo effect has to be worth something, especially when so many spots around town offer $1 bivalves, from La Brasa to Juliet to Waypoint to The Red House (50 cents an oyster for the first dozen!) to Boston Public Market to Marliave to Bastille Kitchen to seriously the list goes on and on.
Gaze over the city skyline
Various
Even if you’re both longtime residents, chances are decent you’ve never hit the touristy-but-cool Skywalk Observatory at Prudential Center and taken in the city’s best views. If money is tighter, hit the Observation Deck at Independence Wharf -- you just need an ID to head up to the 14th floor and watch planes come in for landing over the Boston Harbor. And, of course, there’s nothing like a get-to-know-you cocktail at the Top of the Hub around sunset.
Catch a midnight screening of a cult classic
Coolidge Corner
The first-date movie is an obvious move, but by at least the second or third date you’ll have a better sense of your date's cultural tastes. On Friday nights at 11:59pm, Coolidge Corner Theatre shows B horror movies and other underground showpieces that, if nothing else, will spark spirited convos afterwards.
Convene with the sea lions
Financial District/Waterfront
It’s arguably the city’s greatest simple pleasure: the outdoor harbor seal exhibit outside the New England Aquarium. But did you know you can also book a private, behind-the-scenes tour with the little guys, which more likely than not will include some belly rubs? (For them, not you.) It’s pretty much the perfect way to impress a fellow animal lover.
Co-discover the glories of a proper foot massage
Chinatown
Even if you’re not exactly ready to be rubbing down each other’s hooves just yet, you can definitely outsource the effort in the meantime. Happy Feet Spa is an underground favorite among massage connoisseurs; the one-hour treatment (for $60) includes not only a 30-minute foot treatment, but also a head, neck, shoulders, and arms massage. Make a day of it by grabbing dim sum at nearby Hei La Moon beforehand.
(Gently) mock the talentless for free
Davis Square
The Museum of Bad Art is exactly what you’d guess it is: askew portraits, misaligned landscapes, and nudes that might drive you to never nude-dom. Bond over those less capable than you, then head upstairs to catch a concert at Somerville Theatre (yes, the museum is in the theater’s basement, and admission to it is free with the price of a movie or show ticket).
Challenge each other to a ping-pong showdown
Fenway & North Dorchester
Somehow our city never quite caught ping-pong fever the way others did (we’ll blame Susan Sarandon). But there are still matches to be had, most notably at Dorchester Brewing Company, where the brewery hauls out the ping-pong and foosball tables every Monday night while keeping guests happy with free pizza.
Take a ferry to the South Shore
Hingham
Did you know our public transportation system includes boat service to both the North and South Shores? Hop aboard Kate and Leo–style and head to the Hingham Shipyard for drinks at Alma Nove while staring lustily over the water.
Pick your own star together
Every Wednesday night, winter or summer, the BU Coit Observatory opens up its facilities to the common folk so they can get a far more magnified glimpse of the sky. Name your sun, then return at some later date to see if you can identify it again. Admission is free, but it's a good idea to reserve your spots ahead of time.
Catch disco fever
Harvard Square
The Donkey Show at Oberon has to be experienced to be believed: It's a show full of mirrored balls and feather boas and roller skates and disco tunes galore, all inspired, incongruously enough, by A Midsummer’s Night Dream. The dance party continues long after the show ends; take a spin on the floor and then take all that sexy energy home with you. Tickets are $25 ($15 for student rush).
Eat a delicious speakeasy steak
Downtown
Because by now you know they’re worth it. Behind a red velvet curtain inside cocktail bar JM Curley is the most clandestine of chophouses: Bogie’s Place, where dinner begins with caviar tray service and moves on to your choice of steak cuts burnished with bone marrow and foie gras butter. It's not cheap, but it is worth it.
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Spend the day at the ballgame
Fenway
Boston’s sports scene is in full swing now, and with the weather looking up, it’s the perfect time to take your date out -- to the ballgame. You’re sure to please by treating them to a Fenway Frank and a hefty beer. If the buzz sets in, it might be worth reevaluating the Jumbotron. You can always show your moves off later at Cask N’ Flagon or Bill's Bar. But if you feel the romance calm down a bit, head over to Bleacher Bar or Game On! for more drinks and loud conversation.
Venture off to one of our newest rooftops
Seaport & Theater District
Make the most out of a warm night by meeting at LOOKOUT, Sky Lounge, or Rooftop@Revere -- all set to be opened early May, or any of these other great rooftop bars in Boston. With a cocktail in-hand and some of the best views in the city, you’re sure to start the date off on a good note.
Stare at an impaled skull
Fenway
Because you can still surprise one another. Among the city’s more bizarro museum offerings is the Warren Anatomical Museum, a museum that celebrates the medical procedures of yesterday and displays more than a few human remains -- including the skull of Phineas Gage, who was impaled by an iron rod in 1848, emerging alive but changed personality-wise.
Commit to stretch pants for limited-edition fried chicken
Various
One of the joys of a long-term relationship? Occasionally eating like crap together, forever. Lots of restaurants around town do a solid fried chicken, but it’s the one-off evenings that make it feel special: Fried Chicken Fridays at Townsman, Super Cluckin’ Sundays at Cutty’s (once a month for their fried chicken sandwiches), and Highland Kitchen’s Monday night fried chicken and tiki drink menu.
Explore the endless one-of-a-kind finds at SoWa market
South End
Looking to pick up a few things for your apartment with your SO? Take a day out of the weekend to peruse through the SoWa Open Market, celebrating local artisans, farmers, food trucks, and breweries. After compromising over which art to take home, be sure to check out the DIY Days, with a DIY floral bouquet workshop on June 10 -- a great way to spruce up the place despite not getting your say in the wall art.
Take a stroll through the city's hidden rose garden
Fenway
Featuring over 1,500 roses, this might be your best bet for a casual day stroll -- or even popping a special question if you’re ready for that level of commitment. Part of the Emerald Necklace, the James P. Kelleher Rose Garden is a picture of romance itself. Its pathways throughout the garden are lined with a variety of over 200 roses, benches, and arches -- all leading to a striking fountain.
Rent a kayak on the Charles
Allston/Brighton & Cambridge
Feeling adventurous? Set out for a day on the Charles River. For $21 per hour, take your pick between kayaking and canoeing. If your core is in good shape, paddle boarding is another option for $25 per hour. Meet at the Allston/Brighton or Kendall Square locations to get the date started and once you’ve reached exhaustion, celebrate at the nearest J.P. Licks.
Bond over craft beers, ice cream, and mini-golf
Downtown
Meeting after work? Head to City Hall Plaza’s newest addition -- The Patios -- featuring nine patios, ice cream from Honeycomb Creamery, food trucks, and the “Wachusett Brew Yard” courtesy of Westminster’s Wachusett Brewing Company.
Take a cooking class without leaving the comforts of home
Homestead
Oh sure, you love the idea of “trying new things,” but you also can’t stand the idea of stepping foot outside the house. Cozymeal lets you book an in-home cooking lesson with some of our great emerging chefs -- no changing out of sweatpants required.
Work on your golf swings together
Downtown
For the sunny days, you’ll both want your golf game on point. CityGolf is a good way to let you practice your form, and couples can also opt for customized private lessons, if you're willing to pony up.
Ditch the littles for Adult Night at LEGOLAND
Somerville
Tired of catering to the whims of your friends’ children? Reclaim your time on the third Wednesday of every month when the Assembly Row playland kicks out the young’uns and lets adults ride the rides and play with the exhibits, without fear of disapproval from both parents and kids. It's just $23/person for admission.
Gather your gear and picnic essentials for a beach visit
Revere/Southie
Grab your towels and hop on the train to Revere or Carson Beach for some well-deserved sun and semi-alone time. Revere Beach is just a 0.6-mile walk from the Wonderland station on the Blue Line while Carson Beach is about a half mile from the JFK/UMASS stop on the Red Line. Even if you and the weather aren’t for swimsuit season just yet, shipping off to the beach makes for a relaxing and spontaneous afternoon. If all that's too close and you really want a romantic weekend getaway, though, try any of these stunning beach spots in Cape Cod.
Walk the city's 3-mile pathway along the river
Back Bay & Beacon Hill
The Charles River Esplanade isn’t only a prime spot for running, but it’s only a great place to get some solid hand holding in -- if you’re comfortable. While walking along the Esplanade, stop by the Charles River Bistro for a quick snack and post up at one of the floating docks to watch the dozens of sailboats.
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