Whether it's from an online dating site or via a friend setting you up on a blind date, the first meet-up with someone you don't know very well—or at all—can be a minefield of awkwardness. Of course, chemistry will probably win out, but choosing an appropriate venue for a first date or casual, quick meet-up in the real world needs a little thought. This isn't date night—this is the first step in establishing if there might be a connection. Different strokes and all that notwithstanding, it should be somewhere fun, flirty even, but safe; somewhere very public and with an easy “get out” should it not go well. You can always go with meeting for a drink at one of the best bars in Boston; maybe you want to go classy with a top-notch cocktail bar, or keep it casual at one of the city’s best dive bars.
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The best of the city under one roof
Set in a renovated landmarked Art Deco building, Time Out Market Boston is an ideal spot to casually meet up and hang out. Perhaps start with a drink at one of the bars, and after chatting for a bit, if it’s going well take a stroll and choose from the 15 killer eateries from local culinary heavy hitters such as Tim and Nancy Cushman, Tony Maws, Jody Adams and Michael Schlow.
Best first date spots in Boston
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.
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.
Meet at this big circular bar inside the window-walled ground floor of Mooncusser Fish House. At the bar, the vibe is more social and casual. If things are going well, graduate to a full dinner of sophisticated, seafood-focused dishes in the romantic dining room upstairs, or save that for the second date.
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.
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.
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.
It might not be for everyone, but in many ways Fool's Errand is the perfect place for a first meet-up. It has great drinks, elegant but quirky decor, and some playful snacks, like pricey dollops of caviar served with Lay’s chips, or the potato mille-feuille with raclette and truffle. But it also offers the perfect “get out” because there are no seats and there isn’t even much space; it’s tiny and meant to be the place to go before you go to the place you’re going. Conveniently, sister restaurants Tiger Mama or Sweet Cheeks are mere steps away.
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.
If you’ve established a common love of locally brewed ales, then sample some beers and swap stories at Trillium’s flagship bar and restaurant in the Seaport. The ground floor is a lively, casual hangout amongst the brew kettles—the list is long and there really is an ale for all takers here. If you’ve found a match, grab a bite in the restaurant on the second floor, which usually has a calmer vibe. Or, especially in the warmer months, try for a spot on the pretty roof terrace, where stargazing and beer guzzling go hand in hand.