Great first date ideas in NYC: Where to have a fun first date

Go on a virtual vacation at Bikini Bar

Stepping into this Tribeca coffee shop is almost like walking into a hidden island oasis. Vintage surfboards are propped against the wall, a pineapple-themed chandelier hangs from the ceiling, and coffee cups adorned with palm trees add to the “we’re not in New York anymore” ambience. Swap vacation stories while sipping a cappuccino ($4) at the retro tiki bar; coffee, made from Counter Culture beans, is prepared by regional barista champion Danielle Glasky. 212-571-6737

Grab postwork drinks and dinner

A solid happy hour ($2 off drafts and $5 well drinks until 7pm), bowls of mini candy bars and plenty of board games give neighborhood joint Dive 75 (101 W 75th St at Columbus Ave, 212-362-7518) the low-key atmosphere that lets conversation take center stage. Prolong a successful pairing by suggesting dinner at Celeste (502 Amsterdam Ave between 84th and 85th Sts, 212-874-4559), a bustling spot serving Italian cuisine without the Lady and the Tramp–style trappings that can sink an early-in-the-relationship dinner date. Quaint and comfortable, it’s also inexpensive—every pasta dish is $10–$15.

Sample new brews at Jimmy’s No. 43

• Price band: 2/4
• Critics choice

Loosen your inhibitions and expand your horizons at the same time: Every Tuesday, this East Village drinkery offers a $20 tasting focusing on a specific region (recently, it’s explored Spanish beers). Although experts provide commentary, the experience is casual, allowing you to compare notes—or bios—while you sip. Sop up the booze by sharing a small plate, like the chanterelle mushroom toast ($9) or skillet-fried beer sausages ($7).

Share some laughs at UCBEast

• Price band: 1/4

You haven’t even hung out yet and you’re already giggling at your crush’s Twitter feed. Find out if your senses of humor are truly compatible at this offshoot of the Upright Citizens Brigade Theatre. It’s a low-investment date: Tickets are cheap, as are beers like Bronx Brewery’s pale ale ($6). Check out Airwolf: Let’s Go Back to Your Place (Sat 10:30pm; $10), which takes comedic inspiration from an audience member’s weirdest living situation, and use it as an excuse to share your own hilariously awful roommate stories.

Get a history lesson on the Upper West Side

• Price band: 2/4
• Critics choice

If your prospective date geeked out over The Encyclopedia of New York City in their dating profile, plan to meet in the grand hall of the New-York Historical Society’s Beaux Arts building. There you can explore the annals of NYC—with any luck, wandering through exhibits like “The Landmarks of New York City” (through Feb 18), which showcases photographs of iconic structures, will lead to lively debate.