This guide pairs Boston restaurants with romantic occasions from first dates all the way to milestone anniversaries.
LessDali’s quirky decor—burlesque-themed props, beaded curtains, jamon Ibérico hanging from the ceiling—will calm those first-date jitters. Sip rioja at the blue mosaic-tiled bar—if things are going really well, grab one of the window tables for something more intimate. The menu sticks to tapas standbys like ham croquettes, lamb meatballs, and shrimp cooked in garlic broth, and the delicate small plates are great for keeping the focus on getting to know each other.
Impress your date with a table at this ocean-inspired newcomer. Oyster Bar & Puritan Co. comes from the team behind Puritan & Co., Gepetto, and more. And even though it just opened in 2023, it’s already turning heads for a seafood menu featuring creative riffs you won’t find anywhere else in the city like crab guacamole and lobster toast. If your night is going especially well, stretch it with dessert—hi, PB&J ice cream with miso-caramel peanuts—from ace pastry chef Brian Mercury.
This cozy restaurant bar in the Haffenreffer Brewery complex is the place for a low-pressure hang. The Haven stands out for a solid Scottish menu in a city better known for Irish specialties. Expect an epic single-malt collection and some of the best across-the-pond food in the area like creamy parsnip soup, smoked fish cakes, and haggis. If you’re both into some friendly competition, head over on a Monday for quiz night.
Mooncusser, a three-story spot in a historic flatiron building, promises one of Boston’s sleekest meals. The kitchen here is led by Top Chef alum Carl Dooley, whose seasonal, seafood-forward food includes top-notch crudos. Before or after your celebratory meal, check out LTD Bar downstairs, where techie mixologist Todd Maul pushes the boundaries on cocktails—don’t miss the exceptionally icy martini.
This award-winning hotspot—named one of The New York Times’s best restaurants of the year—is where you go to make serious memories. It’s one of the most sought-after reservations in the city right now, so just scoring a table here is reason enough to celebrate. Woo your beau with the African diaspora-inspired menu, which includes hits like yassa chicken and jerk-roasted duck, and toast your milestone with a cocktail crafted by renowned Boston mixologist and Tanám alum Kyisha Davenport.
Krasi brings the Greek islands to Gloucester Street. The chic mezze bar is a marble-heavy hideaway, known for one of America’s largest Greek wine lists. Go for small plates featuring usual suspects in the cheese and charcuterie department, or get extra-adventurous with lesser-seen Mediterranean options like octopus mortadella and sheep’s milk cheese from Naxos. If your date is going really well, escape to Hecate, a sexy, European-style cocktail bar downstairs.
This classy, multi-floor chophouse is where you go to pop the ultimate question. Dark mahogany panels and enormous columns dial up the grandeur, and the 18-ounce, 100-day aged, salt-encrusted prime ribeye is one of Boston’s finest—and don’t skip the crowd-favorite tater tots with truffle oil. Add a mammoth wine list, attentive service, and a decades-old track record, and you’ve got one of the most reliable proposal settings in town.
If you’re planning on popping the question, you’re in good company at Deuxave, an acclaimed, French-accented stunner. So many couples have decided to tie the knot here that there’s a special table by the fireplace designated for engagements. Feast on artistic plates of seared foie gras, lobster gnocchi, and duck breast with wild mushrooms. If you’re ending the meal with the big question, bring an engagement ring and your server will tuck it in a dessert to present to your SO.
There’s something for everyone at this lively Cuban spot. Doña Habana’s signature over-the-top cocktails, which include a 25-mojito tower with seven separate fruits, were made for good times and group get-togethers. The fish here is arranged vertically and served with a medley of fresh veggies—the striking presentation makes an excellent conversation starter, if you’re all just getting to know each other better.
Frenchie’s gorgeous solarium makes for one cozy date spot, thanks to its ivy-lined glass ceiling and fresh roses on the tables. The salt-encrusted branzino was made for sharing, and so were the restaurant’s signature oysters; to drink, there are bubbles—mostly Champagne and prosecco—for days. If it’s an early-in-the-game date, opt for brunch instead, where can’t-miss options include a white truffle croque monsieur and lobster eggs Benedict.