The Resy Guide to Date Night in Boston

Sure, we like a good industrial-chic dining room as much as the next 21st century diner, but when a night calls for romance, nothing delivers like classical French bistro charm. Long-running South End fixture Aquitaine has that in spades, from its red leather booths to its white tablecloths, tiled floors to wood-paneled walls. But all the Belle Époque bells and whistles would be for naught without the accompanying fare, which Aquataine delivers on with bistro classics including a bone broth French onion soup with aged sherry and steak frites in a shallot sauce with Périgord truffle.

Perched above the Newbury Hotel and boasting panoramic views of Back Bay and the Public Garden, any meal at Contessa feels like a special occasion—and doubly so if it happens to be date night. That feeling should be heightened by a dining room that marries Rat Pack glitz to contemporary design, and a menu of Northern Italian classics including tonnato crudo with anchovy and artichoke hearts, rigatoni carbonara and veal Milanese.

This sleek Seaport restaurant delivers floor-to-ceiling views of Boston Harbor, and its patio provides peeks of the city skyline. However, what matters most is the food, and Woods Hill doesn’t disappoint with locally sourced dishes including grass-fed steak tartare with rosemary and tallow aioli, squid ink casarecce with lobster and crab ragu, and sea scallops a la plancha in a curried golden raisin chutney. Consider toasting the to the beginning — or continuation — of a good thing with a Passport to Paradise (gin, Cocchi Americano, charred mandarin, basil and lemon).

A nautically themed interior evoking the Greek islands gave this pocket-sized taverna enough charm, but its expanded patio allows for seating on two of the South End’s most picturesque streets. Treat your better half to views of Shawmut Avenue or Union Park as you await lamb meatballs, grilled Mediterranean sea bass and your picks from a Greek-centric wine list.

Prezza provides a more elevated take on classic, date night-Italian of “The Lady and the Tramp” variety. Once your table is secure, peruse a menu offering handmade pastas like squid ink spaghetti with clams and garlic in a white wine butter sauce, or ricotta-stuffed ravioli di uovo. Or if the date’s a bit more casual, consider timing your visit to the availability of “Gravy Sunday” specials including chicken parmesan with tagliatelle or veal saltimbocca with roasted potatoes.

If it’s intimacy you’re after, your destination is Lenox Sophia, a South Boston tasting menu restaurant with just 16 seats. Despite the prix fixe focus, the setting and ambience is decidedly casual — ideal if you want the night to be special but low-key. Dinner arrives in five courses of either omnivore or vegetarian fare, which might include a dry-aged Rohan duck with root vegetable hash or tagliatelle with black winter truffles. It also has the locally rare advantage of being BYOB — so do a little research on your companion’s wine preferences beforehand and make it a nice surprise.

Margaritas and tacos are a nice way of communicating that things aren’t too serious or moving too fast—and Burro Bar’s Brookline outpost has ample reserves of both. To be more specific: tacos stuffed with pork carnitas and apple salsa or buffalo cauliflower with whipped avocado, and margarita varietals that come infused with the likes of dragonfruit or hibiscus.

The naturally focused Fenway wine bar is well-situated for a low pressure, getting-to-know-you-date, thanks to a simple menu of sharing plates that includes “snacks” mushroom croquettes with sofrito and grana padano. And when things get a little more serious, you may want to return for the crispy pork belly with apple mostarda or chilled octopus with smoked tomato crema.

Talulla’s eclectic menu is bound by a focus on local farms and seasonality, but you can just as easily imagine that its dishes were chosen for maximum date night-appeal. As evidence, we’ll submit such choices as foie gras torchon with pomegranate and cranberry on brioche, whole wheat lumache with escargot and garlic herbs, or cod and lobster accompanied by mushroom and bok choy,

Asta’s charmingly mismatched cutlery and schoolhouse style chairs and tables diffuse the high-stakes pressure that can come with the tasting menu date, but the six-course selection — you’ll choose between vegetarian and omnivore iterations —  delivers the goods. The former may include sunchoke with sunflower seeds and parsnips with zhug, while the latter might feature cod with horseradish, or beef accompanied by spring onion and fennel purée.