In a city full of hopeless-romantic singles, nailing the first date is a crucial step. If you'd rather not hole up in a dark dive bar or embarrass yourself at museums with your limited knowledge of art, you can always fall back on the old-school wine-and-dine with the city's best restaurants and bars. From a cozy drinks den to a romance-ready rooftop taqueria, here are the best spots to kick off your journey to true love.
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Restaurants and bars for a first date
Equal parts salon, pub and bordello, Oscar Wilde serves a broad mix, including tipples in the Victorian style and Prohibition-inspired cocktails (the building previously housed the Prohibition Enforcement Headquarters) despite the fact that Wilde died 19 years before the Volstead Act. And there’s champagne, of course. (The menu quotes Wilde: “Pleasure without champagne is purely artificial.”) The venue is awash in deliriously decadent bric-a-brac like painted-glass windows and crushed-velvet chairs, without the impotence of being earnest—and almost everything is dolled up with ornate chandeliers or heavily lacquered wood.
Conversation starter: All that marble? Yeah, it's real.
The cocktails are enough of an experience on their own at the Last Word. Candlelight replaces now-cliché incandescent Edison bulbs as velvet curtains, along with tufted leather armchairs and love seats, add texture for all the senses. On a recent visit, we saw a nearby couple request a seat change from two armchairs to one loveseat; it was granted, and they expressed their gratitude by quickly becoming quite, um, loving.
Conversation starter: Recently the Last Word renovated, turning the front into a proper part of the bar and shedding the theatrical pretense.
Veteran shufflers and court virgins alike are welcome at this surprisingly hip, out-of-the-box date spot, with 10 regulation-size lanes and a league for those who actually know their cherries (scoring in the 10-point box on the last shot) from their pepperonis (all four biscuits in scoring position).
Conversation starter: If biscuits and tangs aren't your thing, challenge your date with a Giant Jenga or Connect Four match.
This Italian wine bar and restaurant from Manhattan’s Massimo Felici (La Nonna, Ribollita) is elegantly understated with house-baked breads and pastries, small Italian plates (meatballs, burrata) and vintages from Italy and California from the glass or bottle.
Conversation starter: "Have you ever ridden the Staten Island Ferry before?"
At first glance, it doesn’t look like much: Tucked between a neighborhood bodega and a Latin religious-articles shop on Broadway in Hamilton Heights, ROKC is an unadorned semi-subterranean room, paint cracking on its white walls and a handful of two-tops crammed in front of a long wooden bar. But it is what’s behind that utilitarian bar that warrants the trek—it’s not the curious upturned lightbulbs or conch shells neatly set on shelves amid copper Mule mugs, golden pineapple goblets and mini barrels aging cocktails. No, it’s Shigefumi Kabashima and Tetsuo Hasegawa, the former Angel’s Share cohorts who serve some of New York’s most stunning drinks.
Conversation starter: Play the guessing game for the ROKC acronym (“ramen, oysters, kitchen and cocktails,” FYI).
They don’t make ‘em like this any more (probably because Health and Safety would shut ‘em down). West Village hangout the Fat Cat is a basement bar and pool hall where the sofas are scruffy, the drinks are cheap and the ambience is jovial. Closing time is 4am if you're really hitting it off.
Conversation starter: There’s live jazz every night, and Fridays have included formidable Brooklyn soul singer Naomi Shelton playing a residency with her Gospel Queens.
Like its menu—playful, beach-ready cocktails and exotic snacks—Ravi DeRossi's teal-and-white tiki den is rife with time-warp nods to the Pacific isles, including retro floral-patterned banquettes, hand-carved totem pole stools and mother-of-pearl light fixtures. The effect is somewhat dreamlike and downright romantic, corroborated by a lo-fi pop soundtrack ranging from the Velvet Underground to St. Vincent. If you can brush off the occasional stares of passersby—the gleaming neon sign and effervescent lights garner many a sidewalk double take—you might find yourself lost in booze-soaked first-date bliss.
Conversation starter: Order the Shark Eye, a Jaws-esque cocktail that'sone of the most Instagrammable in the city.
Named after a 1932 Surrealist poem by Paul Éluard, the cocktail bar’s odd moniker is not made any clearer by the sentences etched on its front window: THIS IS NOT A BROTHEL. THERE ARE NO PROSTITUTES AT THIS ADDRESS. It’s a wink-wink phrase hinting at the location’s past: The spot at 257 Smith Street was a short-lived “massage parlor” before it closed last December. The narrow rooms are reminiscent of a Sleep No More chamber, adorned with oversize double-starburst mirrors. A collage of yellow-paged open books lines the walls, and old-world potion bottles and women’s vanity knickknacks are strewn on counters.
Conversation starter: Slinky nods to its illicit past include a red light bulb hanging above the doorway and a bona fide canopy bed in a back room.
The East Village icon may have gotten a first-date-ready spruce-up—duct-taped booths traded for green banquettes, neon beer signs for gold sconces—but it's still as lively as ever. Frequenters of the original will breathe easy seeing that the battered red awning, wooden phone booth and signature horseshoe bar remain. Dressed-down groups in their twenties and thirties convene over drinks at the back tables, with the din of laughter regularly overtaking the ’80s deep cuts spilling from the speakers.
Conversation starter: There's a restored harem-girl mural, dating back to the 1920s when the bar was known as Ali Baba Burlesque.
The name conjures a psychedelic den with Agnes Moorehead or Stevie Nicks tucked into crushed-velvet booths, but Mood Ring defies expectations. There are velvety booths, but also a homemade arcade game called Yo Fight My Mans and erratic art, including red sneakers dangling from the ceiling. It’s, like, very L.A. The Outkast, a liquefied flower-crown of rose and lavender, resonated once the unnecessary seltzer ran dry and the sunken rose syrup flourished (the rose petal in the ice cube was cute, though). The electric blue Mercury in Retrograde dazzles as a green-tea spin on Long Island iced tea. The fiery shot Aux Cord—vodka, sriracha, tomato juice and Tabasco—lashes audacity as it spills like daybreak across the tongue.
Conversation starter: "What's your sign?" (Duh.)
Plush carpeting controls the acoustics at this auto-repair shop turned restaurant. The garrulous crowd gathers under faded paintings and timeworn mirrors to feast on generous portions of burekas (feta-stuffed phyllo), thyme-laced haloumi cheese wrapped in grape leaves, and tuna steaks swimming in red-pepper puree. Regulars are as devoted to the live music as they are to the Mediterranean menu: Jazz performers wail Tuesdays between 7:30 and 10:30pm and on weekends from 1 to 5pm.
Venue says: “SoHo's best kept secret for over a decade. Lunch, Dinner, Brunch on weekends, and live Jazz music every night!”