Once the initial inspection is over, suss out whether you and your date’s tastes are simpatico by ordering a make-your-own cocktail ($11), combining your choice of liquor and fruit or veggie juices. Or calm your jitters by ordering one of the specialty drinks ($13), such as the Energy Memory Punch, which mixes rum with pineapple and orange juices, mango nectar and fresh mint.
This laid-back East Village beer bar and shop offers 12 frequently rotating taps, which often include brews from local outfits (such as Rockaway Brewery), along with Alphabet City’s own Easy Blonde ($6). If you’re picking up a bad vibe, order a half-pint ($3–$3.50) to save time, calories and cash. And if it goes really poorly, console yourself by choosing from the more than 350 bottles available to make a custom six-pack ($8–$14). You deserve it.
When it comes to suggesting a suitable meeting spot, easy access to transportation and plenty of seating are essential. This Park Slope bar, five blocks from the Atlantic Ave–Barclays Ctr subway station, has both, along with enough beers to satisfy craft-brew fanatics and those who just want to ease into first-date chitchat. Sip on an Anchor Liberty ($6) and let the alt-rock–leaning soundtrack prompt questions about your favorite bands.
Can’t decide between meeting for coffee or drinks? This Dumbo bakery—an offshoot of the Cobble Hill original—lets you opt for both. Choose from a rotation of six wines and five beers, or go for caffeine over alcohol with a cappuccino ($3.75). When it starts getting dark, the manager dims the lights; come in the late afternoon and grab a seat by the counter, where the immense windows provide a romantic view of the neighborhood at dusk.
Assess your possible connection with a clear head by grabbing dessert at this bakery, which has romantic low lighting and cozy tables. Start a conversation while snacking on sweets like the shop’s famous buttermilk pie ($5.75); if it goes well, linger over a cappuccino ($3.75) and play a board game like Battleship or Trouble. The shop is open late—until 10:30pm during the week, and until 1:30am on weekends—so there’s no need to rush.