So you've both swiped right, and now it's time to pick a spot to meet for the first time. You're looking for something casual (in case things go off the rails), but still fun and sociable (in case they go better than expected). From an atmospheric cup of coffee to a low-pressure meal, here are five affordable spots in Boston that are perfect for those occasionally awkward initial meetings, no matter how they turn out.
After-Work Happy Hour: BISq
Inman Square
While Boston has no cheap happy-hour booze to smooth out that initial round of getting-to-know-yous, you and your date can at least embrace your sensual side by slurping down some $1 oysters at this cute wine bar (offered from 5:30-7pm Monday-Thursday). Pair them with a glass of sangria, and if the conversation takes off, keep it going with a bottle of red and some of the famous housemade charcuterie.
A Cup of Coffee: Thinking Cup
Boston Common/North End/Back Bay
Wifi is verboten at this trio of coffee shops, which means you won't have your conversation interrupted by someone's clacking keys (or vice versa). The intimate, dimly lit atmosphere has the advantage of feeling like a bar without actually being one, and if the conversation flags, you can always chat about the quirky headlines in the 1800s-era newspapers that cover each tabletop.
Playing a Game Together: A4cade
Kendall Square
Pinball, skee ball, Street Fighter: everyone's got a favorite arcade game, and you can test your date's mettle at this fun underground gaming bar, which has the bonus advantage of no tykes to compete with (it's strictly 21+). Grab a boozy Kill Screen slushie or a pint of Notch Pilsner and face off in a round of foosball or Ms. Pac Man, then chill out and make conversation over a couple of Roxy's grilled cheeses.
A Fast-Casual Meal: Aceituna Grill
East Cambridge/Kendall Square/Seaport
A sit-down meal can sometimes be too much pressure for a first date, so if you're looking to grab an easygoing bite, the counter-only service at this duo of Mediterranean restaurants is the perfect fit. The menu has lots of options for vegetarians, vegans, and the diet-conscious, ensuring picky dates will have something to eat, and it's adaptable to different hunger levels: you can share a light after-work snack of hummus, baba ghanoush and pita, or opt for a full meal with a shawerma or falafel salad or rice plate.
Dessert For Two: Caffe Vittoria
North End
For a cup of coffee and something sweet, enjoy a Roman holiday at this Italian cafe in the North End, where the espresso is strong, the cannoli are crispy, and the boozy coffee and hot cocoa are the perfect pick-me-ups on a chilly winter evening. Split a slice of cheesecake or a few flavors of gelato, and see if any amore develops.
