Bar Enza
Photograph: Courtesy Bar Enza

The 10 best first date spots in Boston

When scoping out a new romance, dining at these spots in Boston can help you see if there are sparks

Cheryl Fenton
Written by: Linda Laban
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The first meet-up with a potential love interest is always exciting. There are already plenty of questions—what to wear, what to say, what to feel—so we’re here to help you answer at least one inquiry: where to go. From relaxed menus to conversation-ready atmospheres, these places take the stress out of the first date and allow all the relationship potential to shine (or not). If you don’t want to commit to more than a short time together just yet, grab a drink at one of the best bars in Boston or these top-notch cocktail bars.

RECOMMENDED: Full guide to the best things to do in Boston

Best first date spots in Boston

  • Italian
  • Harvard Sq
  • price 3 of 4

You are bound to score extra points for choosing this Cambridge hot spot, but be sure to make a reservation for a couple of seats at the bar. Drinks change seasonally and are beautifully concocted with aromatics, and finished with spritzes of flower water. If the conversation’s flowing, share a couple of small plates, or go for broke with the signature Lumache Bolognese, a funky twist featuring Korean gochujang.

  • Hotel bars
  • Seaport District
  • price 2 of 4

OK, so you have established that you will meet for drinks at this popular Seaport rooftop bar, but whether you want to take it to the next level—that is, actually breaking bread with a relative stranger—can be decided later. It's hard not to be impressed by the views of Boston Harbor and city skyline. For dates during the wintertime, the rooftop’s cozy igloos are open on a first-come-first-served basis, and your seat is amongst a group, so no worries about awkward alone time. If you want to keep things going, pop down to the ground floor for a swoon-worthy bites at Outlook Kitchen.

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  • Museums
  • Art and design
  • Fenway/Kenmore
  • price 2 of 4

For the culturally minded, this expansive museum is, of course, a great place to absorb art and culture, but it’s also a great place to have a wander and chat while determining if there’s any commonality. The country’s fifth-largest art museum has everything from abstract masterpieces to Egyptian sarcophagi, after all. If you aren’t running for the exits after perusing all the art, head upstairs to the museum’s 465 Bar and Restaurant, a super sleek spot decked out in ivory and blond tones, with a full bar and a menu of New England-inspired small plates.

  • Latin American
  • Back Bay
  • price 2 of 4

Sister restaurant to the Mediterranean-inspired Kava Neo-Taverna, this intimate crudo and ceviche bar could set the mood for a Latin-inspired love connection. A modern underground space of whitewashed brick and graffiti, it’s the perfect place to make a great first impression. The wine list mirrors exactly what you hope your companion will be, with categories including Inviting & Charming, Flirty & Refreshing and Cool & Smooth.

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  • Italian
  • Harvard Sq

Sink down into the rose-colored velvet banquets at this newly opened neo-trattoria inside Harvard Square’s Charles Hotel for comfortable conversation that hopefully flows as easily as the drinks (their Italian-focused wine list is stellar). The menu is crafted by Chef Mark Ladner, who recently returned to the area from a NYC stint that earned him a James Beard Award, and has an extensive antipasti station perfect for sharing, as well as his famous Hundred Layer Lasagna. Is that amore?

  • Bakeries
  • Back Bay
  • price 1 of 4

Choose one of this Walpole, NH-based chocolatier’s pretty cafes in either Cambridge or Boston, and step inside a café experience far above the usual laptop-and-phone crowds. This old school, Continental European-styled café is a nice place to relax and converse while sipping a refined coffee or creamy hot chocolate. If you’re sensing some sweet feelings, order a couple of sumptuous pastries or some of the exquisite handmade chocolates.

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  • American
  • Back Bay
  • price 2 of 4

This casual Back Bay spot solves the “where should we go” dilemma by serving up some of Boston’s most famous chefs’ dishes all in one place. Chef Brian Poe and his team recreate (with permission, of course) mile-high sandwiches made famous by local chefs, like Jody Adams, Ken Origner, Jamie Bissonnette, Tiffani Faison and even Poe himself (his Meatloaf Club is legendary). Take a seat at a window nook and order dishes that satisfy you both, leaving the hard decisions to the second date.

  • Contemporary American
  • Downtown
  • price 3 of 4

A modern day supper club in downtown Boston with a speakeasy vibe (yes, you have to walk through a faux barber shop to get in), this place has a rich decor and even more decadent food. Dimly lit crystal chandeliers are clustered in front of the original Santo Domingo mahogany bar, while sexy craft cocktails, a gilded fireplace, Damask walls, velvet club chairs,and tufted couches are guaranteed to help loosen up any nerves.

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  • Ice cream parlors
  • Jamaica Plain
  • price 1 of 4

An ice cream date might seem a little coy, but who doesn’t like ice cream? Even the dairy intolerant and vegan can enjoy a scoop at J.P. Licks. The locations in Davis Square, Harvard Square, Charles Street and Coolidge Corner are surrounded by interesting street life, so why not enjoy a stroll once you’ve consumed your cone.

  • Hotels
  • Chinatown
  • price 3 of 4

The street level lounge at the W in the Theater District works as a meet-up on many levels. In the early evening, and earlier in the week, it’s a relatively quiet, yet classy, place to have drinks. If you’re comfy going knee-to-knee at the bar, fine, but the cushiony window seats offer a more comfortable relaxed perch and some amiable distance. The central couches by the fire pit are perfect for cozying-up if there’s an instant connection, and the street views provide conversation starters. Later at night and on weekends, the lounge is abuzz with a high-energy, clubby atmosphere.

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