18 Brooklyn Dates: One for Every Conceivable Dating Scenario 


The Art Date

Conveying one’s cultural sophistication and in-the-know hipness while enjoying free booze with romantic interests is why we have art gallery openings.

6pm: Odds are, if it’s a Thursday, Friday or Saturday, one or more of the galleries at 56 Bogart Street is having an event. Get there early to ensure you’re able to put away a few PBRs or plastic cups of box wine before supplies run out.

8pm: Apartment galleries and artist-run spaces operate on their own schedules, so if there’s an opening at one of the local DIY galleries—nearby options include Centotto (250 Moore St), Factory Fresh (1053 Flushing Ave) and English Kills (114 Forrest St)—odds are it’s starting late and going later.

10pm: The gallery party is migrating to a bar, but you’re hungry and in need of some quiet one-on-one time. The kitchen at Brooklyn Fireproof East(119 Ingraham St) is open until 11, and the affordable fare is just what you’ll need to soak up all that cheap alcohol. Be sure to peek into the big space in back of the dining room, which often doubles as a gallery—there might be more art to look at while you wait on your entrées.

11pm: Invariably—and happily—the night ends at The Narrows (1037 Flushing Ave), where the elegant bar gets crowded quickly, but the leafy backyard is full of nice places to snuggle up and sip.

"Maybe even go for a spin on Jane's Carousel?"

The Win ‘em Over Date

Tacky as it sounds, neither rooftop party nor loft concert can compete with the wow factor of the view from between the Brooklyn and Manhattan bridges. Seal the deal in Dumbo.

7pm: Arrive aboard the East River Ferry to heighten that “Holy shit New York City!” effect.

7:15pm: Sweeten the deal with a rich cup of hot chocolate from Jacques Torres (66 Water St) while you walk through Brooklyn Bridge Park. Maybe even go for a spin on Jane's Carousel?

8pm: Whatever show is on stage at St. Ann's Warehouse (38 Water St), it’s likely very good, and without fail technically spectacular. This month it’s the Wooster Group and New York City Players doing a series of early Eugene O’Neill plays about sailors, specifically the longing of being away from those they love while at sea. How apt!

10pm: It’s at the other end of the neighborhood, but the trek to Vinegar Hill House (72 Hudson Ave) will be worth your while, specifically for its ability to transport you from the quintessential urbanness of Dumbo proper to the quaint village vibe of Vinegar Hill. It helps that the setting oozes romance, and the food is damn good too.

11:30pm: If you need to have one more trick up your sleeve (you’re doing something wrong!), grab your date by the hand and slip around the corner to check out the amazing Commandant's Mansion perched atop Vinegar Hill on Evans Street, which happens to also be a great make-out spot. Now take him/her home already!

"Proceed to get properly boozed, point out passing planes, sit in silence..."

The Roof Date

Ah, there are few things more romantic than taking in a sunset on a Brooklyn rooftop. Just keep a weather eye out for pigeon crap. Oh, and ledges.

3pm: This isn’t going to be one of those “let’s drink forties while you listen to me play my guitar for you” dates. Go stock up on a few bottles of grown-ass people wine and cheese at Uva Wines (199 Bedford Ave) and the Bedford Cheese Shop (141 N 4th St).

3:30pm: Prep isn’t done yet. If you think you can handle not burning down your own apartment building, pick up some handmade,Brooklyn-themed candles from Owl and Thistle General Store (720 Franklin Ave). Blankets are also a nice, thoughtful touch, as well as an excuse to snuggle feel each other up on a cold night.

4pm: Pick up your lover and ascend (HOLDING HANDS!) to the roof. Proceed to get properly boozed, point out passing planes, sit in silence, listening only to trains rattling over tracks and the furtive beating of each others’ hearts. You can even pull a Titanic and take turns holding each other and standing at the edge of the roof with arms outspread humming “My Heart Will Go On.”

6pm: Damn, this was a great idea, but it’s effing freezing. Luckily, someone’s warm apartment is only a few flights of stairs below. You know what that means. Bow chicka wow-wow. (Is what sex sounds like.)


The Bike Date

Foreshadower of sex—with all its pumping, sweating and messy hair—the bike date not only provides the perfect pretext to share a shower afterward, should said pretext even be needed, but also affords an opportunity to explore public transportation-averse sections of our borough. To Red Hook!

4pm: Meet up at local bike shop Dog Day Cyclery (115 Van Brunt St) for any last-minute tune-ups and accessories. Don’t underestimate the romantic eloquence of a judiciously rung bike bell.

4:30pm: Bike down to the waterfront—take Imlay and Conover streets rather than Van Brunt for more scenic, less traffic-heavy side-by-side riding. If the weather’s nice, pop into Fairway (485-500 Van Brunt St) for supplies, then ride (careful, cobblestones!) to Valentino Pier and Park (at Ferris and Van Dyke streets) for a waterfront picnic at sunset with the ultimate wingman, Lady Liberty.

6pm: For dessert—or dinner, in cooler months—head to low-key eatery The Good Fork (391 Van Brunt St). Be sure to get at least one slice of Steve’s key lime pie, from the nearby bakery and waterfront institution.

8pm: Cozy up for the evening in a booth at Sunny's (253 Conover St), a museum piece of a watering hole where, if not for the excellent live music on most nights, you could still hear the mournful fog horns of tugboats passing in the night. Drink responsibly, you still need to ride home—much as you’d like to, you can’t stay here.

The Rom-Com Date

When you play back this date in your head, it will be a montage, scored to the Stereophonics’ “Have a Nice Day.”

2pm: The New York Aquarium (602 Surf Avenue). Laugh and nudge each other as two frisky penguins shake water all over each other. Cut to:

3pm: 3pm: Win a stuffed bear at roll-a-ball in Luna Park. Scream as the Cyclone threatens to collapse beneath you. Gaze across the twinkling city from atop the Wonder Wheel. (Actually, Coney Island’s amusements are shut down until spring. You could wait, or else stand on the deserted boardwalk, the wind biting your face, and gaze silently upon the gray and fathomless sea. But that would be a very different movie.)

5pm: Hoo boy, those hot dogs at Nathan’s (310 Surf Ave) sure do lend themselves to some sexually explicit food-flirtation, don’t they? Now cut to the next scene, eliding the interminable subway ride back.

"This is less of a getting-drunk thing and more of a strictly educational endeavor."

The Broke Date

They say being a starving creative professional is sooo romantic, but “they” clearly have no idea what a strict diet of rice and beans does to a person’s libido and digestive system. Being broke actually takes a lot of effort to make bearable. Here’s a date to make the best of your pitiful paycheck.

5pm: Take one of the Brooklyn Brewery’s free Saturday tours (79 N 11th St), running on the hour, every hour between 1 and 5pm. The one catch is that beer tokens are $5 each, or 5 for $20, so this is less of a getting-drunk thing and more of a strictly educational endeavor.

7pm: You wanted to conserve the dwindling amount of spaghetti you have for the week, so head on over to Bushwick’s famed Tortilleria Mexicana Los Hermanos (271 Starr St). Nosh on arguably the borough’s best tacos, tortas and quesadillas while the factory’s employees roll out fresh tortillas in the back. The best news? No one item exceeds $4.

8:30pm: Cuddle up with those beers and have yourselves a good ol’ Planet Earth marathon on the couch. Reassure one another that you are having way more fun on this date than anyone ever could doing something expensive.

The “Let's Make Dinner” Date

The Let's Make Dinner Date always sounds like a good idea, and for evolved couples, it can be a mutually enjoyed activity. But, come on, let's be honest. We know that most of the time it's really one person who "makes" dinner while the other person just stands there. Still, it's worth a try.

Anytime: Invest in the The New Brooklyn Cookbook, and find the recipe for a favorite dish from a local Brooklyn Joint. The content is culled from restaurants that "put Brooklyn on the culinary map," including Al di La, Roberta's, Vinegar Hill House, Buttermilk Channel, and 27 others. You’re bound to find one where you’ve dined.

Saturday, before 3 pm: : Pick up fresh produce from the McCarren Park Greenmarket. Delight in free samples.

5pm: Start cooking, and don't forget to delegate responsibility. If you're the type who likes to sit back and watch, at least offer to do the dishes.*

*This is very important, otherwise you will lose brownie points. Trust us.

" You probably should eat something before you pass out"

The Just Drinks Date

The Just Drinks Date is a versatile animal. Perhaps it’s a first “pre-date” of sorts, in order to suss the other person out and see if he’s worthy of dinner. Or maybe it’s your kajillionth non-date date, the kind where everything is “chill” and “non-committal” and like, “god no, not a real relationship.” Either way, the objective is to get hammered, which may or may not end in the Perfunctory Let’s Just Go Have Sex scenario (see below).

8:30pm: There’s nothing like a meticulously crafted, fancy cocktail to start off an evening. Go locate some over at Huckleberry Bar (588 Grand St).

9:30pm: You’re ready for a change of scene. Why not an Austro-Hungarian Beer Hall? Try Radegast Hall & Biergarten (113 N 3rd St), then attempt to drink your body weight in alcohol. Your date can’t finish his pint? Tease date mercilessly until he does.

11pm: A different place! A dfrefent plaaaaaaaace! Wanna go eat sum cheesebaaaaaawls? Good idea. You probably should eat something before you pass out, but in the meantime, cross the street to The Levee (212 Berry St) for some drunken board games, $5 Frat Boys and a jukebox that, while cool, will never, ever play your selection.

1am: Whether you’re in your bed or someone else’s, make sure to have imbibed lots of water. Also remember to use the bathroom (sinks and corners are verboten) to pee, and sleep on your side. Sweet dreams.

The Treat-Yourself Date for the Single Person

Hey, how are you doing? Do you need a little me time? (Or should that be "you time"?)Yeah, so do we. You've earned it buddy.

4:30pm: No "Treat Yourself" date would be complete without a treat. Do it right by starting at the Mast Brothers tasting room (105A North 3rd St). Thursdays, Saturdays and Sundays they even offer tours of their chocolate-making factory. It's like Willyburg Wonka.

6pm: You need some new threads. I mean, you look good and all, but a nice sweater or pair of jeans might ensure that you won't be treating just yourself on your next date. Check perennial second-hand shopping hubs Beacon's Closet (88 North 11th St) and Buffalo Exchange (504 Driggs Ave) for your new signature fashion item.

8pm: There's no shortage of comfort food options in Williamsburg, in fact there are too many, but we're still partial to Jimmy's Diner (577 Union Ave). Claim a seat at the bar and have a few beers with your greasy feast—or a nice, thick milkshake, if you're going all out.

10pm: The most self-indulgent activity that can be practiced in public (legally) is playing vintage video games, and Barcade (388 Union Ave) has an amazing selection of them—not to mention all those beers on tap. And hey, most of their nostalgia-stroking arcade antiques are two-player, so who knows, this date might end on a not-so-solo note after all.

The Blind Date

“You have so much in common!” Well, the human genome is 99 percent similar to that of a chimpanzee, so, yeah, sure you do, but still. [Fun fact to bring up on your date: the much- and indeed quite recently vaunted similarity between the human and chimpanzee genome has in fact been somewhat overstated, due to selective sequencing. But, again, still. –Ed.]

1pm: Who the hell is this person, anyway? Find out by going on a date somewhere very well-lit, with a conversation piece that’ll overcome any initial awkwardness, and bring any cultural/psychological/political/religious/sexual dealbreakers out to the forefront early. HIDE/SEEK: Difference and Desire in American Portraiture, featuring taboo-busters from Mapplethorpe and Wojnarowicz to Neel and Leibovitz, is at the Brooklyn Museum (200 Eastern Parkway) through 2/12.

2:45pm: So, since neither one of you has stalked off to Grand Army Plaza in a rage of demographic solidarity, it’s time to test actual interpersonal compatibility. The Sunburnt Calf (611 Vanderbilt Ave) has an all-you-can-drink brunch and good-timey Aussie servers—it’s both conversational lubricant and a helpful early-warning system for worryingly low or high tolerance.

4:15m: That went well, right? (Right?) Reflect over a coffee at Outpost (1014 Fulton St), and use the wifi to check whether they’ve friended you on Facebook yet.

The Cemetery Date

The opposite of death isn’t life—it’s sex. So there ought to be no better place to get that certain someone totally into you than one where you’ll both be surrounded by headstones, sepulchres and mausolea. This is gonna be us one day, baby; better live our lives to the fullest while there’s still time.

2:30pm: Great thing about Green-Wood Cemetery (500 25 St) is that not only is it a beautiful landscape, but also its main gate closes at 5pm, making it a perfect spot for one of those weekend-afternoon dates that’s easy to get out of if it goes poorly.

3pm: Show off! Seek out Leonard Bernstein’s grave and discuss how the role of the maestro as a public figure has changed. Locate the Statue of Minerva and wave hello to the Statue of Liberty. Recite passages from your Master’s thesis about how cemeteries are a relatively new phenomenon and probably long-term unsustainable in their present form.

5pm: Hey, that wasn’t so bad. And now you can go get a drink, thanks to the bourgeoning South Slope bar scene. May we recommend the friendly Bar 718 (718 Fifth Ave), or the pristine tap lines of Mary's (708 Fifth Ave)—or, c’mon, let’s be serious, both?

8:30pm: Oh, you shouldn’t have started drinking so early. And you definitely should have gone out for dinner first.

"Take in the sunset one last time (metaphor!)"

The Last Date

So, this is it. You’ve decided, once and for all, IT’S OVER. Whatever speech you have planned (“Welcome to Dumpsville, population, YOU!”) it’s probably best you keep this date to busy public areas, to discourage violence and/or tears.

5pm: Take in the sunset one last time (metaphor!) with a stroll around the newish part of Brooklyn Bridge Park, grabbing some consolation ice cream from Brooklyn Ice Cream Factory (Old Fulton and Water Sts).

6pm: Superfine (126 Front St) is usually pretty bustling and loud, so hysterics will likely be masked in the high-celinged din.

Approx. 6:45pm: The nice thing here is that when your newly ex significant other leaves before the entrée course, you can just have it re-routed to the bar, where you can begin getting tanked. (BONUS: Be on the look-out for overworked/undesexed Dumbo creative professionals deep into their third pistachio martini.)

The "Is This a Date?" Date

3pm: "Sure, a movie sounds fun. Why don't you meet me in the park and we'll walk over there together?"

3:01pm: Did she say "fun"? What does that mean?

7pm: Is walking through Prospect Park something friends do? Or something dates do? Does the fact that it's winter mean it's more romantic, or less?

7:30pm: One for the Money? Why on Earth does she want to see One for the Money at The Pavilion (188 Prospect Park West)? Are we going so we can make fun of it ironically later? Or does she think that moving forward it'll be a good guide for our relationship?

7:40pm: Why am I "getting the popcorn" and she's "getting the drinks"? Is it some kind of 90s-style Dutch agreement? Who even buys drinks at a movie theater?

8pm: No seriously, why are we watching this?

9:30pm: If I pay for her beer at Black Horse Pub (568 Fifth Ave), will it be weird? If I don't, will it be weirder?

11:45pm: Friend or date, whatever—walk her home, dude! This area's not safe!

12am: Just kiss her goodnight, stupid. It's a date if you want it to be (even if it's your last, pushy lips).


The Long-Distance Skype Date

So what you really miss, every since your Sig. Oth. moved to Portland, is the little things—the casual one-liners and doofy expressions that spring up organically in the course of day-to-day life. For this wifi-enabled date, we replicate that as closely as possible, give or take the smells.

4pm: McCarren Park now has free public wi-fi; lay out your blanket, prop open your laptop, and sit opposite it, reading and looking up occasionally to remark upon the girl wearing leggings in this weather.

5:15pm: Happy Hour! Settle in opposite your laptop at The Mark Bar (1025 Manhattan Ave). People will just think you’re working!

8:30pm: Hoo boy, you stayed at Happy Hour longer than you intended to. Better head straight home for some Skype Sex.

"Stifle that yawn, you boring married person"

The Married Date

Miss going out and doing something nice (“trying a little,” in your unkinder moments), but not the improvisatory subtext that plagues newly formed couples everywhere?

6pm: BAMcinematek's annual Valentine's Day Dinner and a Movie features a three-course prix fixe, followed by an 8:30pm screening of Lubtisch’s dazzling The Shop Around the Corner (you know, You’ve Got Mail with Jimmy Stewart doing a Hungarian accent).

10:15pm: Stifle that yawn, you boring married person, and don’t be the first one to admit you’d rather go home than stay out for a drink. Stonehome Wine Bar (87 Lafayette Ave) is quiet, and pleasingly bereft of the Youngs and their aura of sexual possibility.

"...keep an eye out for green shoots fighting upward through the thawing soil of your heart."

The Rebound Date

“I remember the last time I was here, with my ex…” “This reminds me of the time when me and my ex…” “Oh, look, over there, it’s my ex…” Please. Stop. Make new memories.

3pm: You never went to theBrooklyn Botanic Garden when you were together? So much the better. Call in sick (heartsick!) to take advantage of the free winter weekdays, and keep an eye out for green shoots fighting upward through the thawing soil of your heart.

5pm: Soothe yourself with wine and jazz at Abigail (807 Classon Ave), and try not to wince as gentrifier parents come in and out, folding and unfolding their children’s scooters, and reminding you of the children you never had.

7pm: This is not going as expected. Eat your emotions at Dutch Boy Burger (766 Franklin Ave), and note that the bathrooms are shared with Franklin Park (618 St. John’s Place), so you can sneak through while “washing up before we pay” (read: crying surreptitiously into a quick beer).

"They also have Connect Four."

The Perfunctory Let’s-Just-Go-Have-Sex Date

If you want to at least try being outside together to see how it holds up, without making any major experiential commitments or expectations-upping financial transactions; or if you’re still in the tear-each-others’-clothes-off stage but want to attempt a decently rounded evening, try this, or at least however much of it you get through before cabbing it back to your candlelit bedroom and suede water mattress.

5:30pm: The enclosed booths opposite the bar at the dimly lit Black Rabbit (91 Greenpoint Ave) are ideal for canoodling, if you’d like to hedge your bets. They also have Connect Four.

7pm: Santa Fe (366 Union Ave) has potent tequila cocktails and light Mexican fare, so you can steep yourself in the aphrodisiacal powers of the chili pepper without unsightly bloating.

8pm: Videology (308 Beford Ave) probably has a DVD of Terence Stamp and Julie Christie in Far From the Madding Crowd, the film with which humanity achieved Peak Hotness.

The Proposal Date

The Cyclones don’t start up again until summer, and the Nets don’t move here until next season, so unfortunately there are no Jumbotrons at your disposal.

6:30pm:If you’re going to drop a knee, quite honestly, you should do it somewhere with personal significance to you and your beloved. Why would you take proposal advice from a free magazine? This blurb is probably being written by an intern whose most successful relationship lasted for seven glorious minutes in the bathroom at Sophie’s. But ok. The River Café (1 Water Street), in the armpit of the Brooklyn Bridge, with its dazzling Manhattan view, is maybe our borough’s schmanciest restaurant. Here’s what you do: make a reservation for two. Stand your date up. Call, say, sorry I’m running late. “Are you near music?” Say, “What do you mean?” Her: “It’s just that I thought I heard—no, I do hear Peter Gabriel’s ‘In Your Eyes.’ It’s getting closer!” Say, “Oh, that. Well, look outside.” She goes to the window. Boombox. Arms. Bam. Grandkids.

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