Williamsburg Date Guide Straight From a Brooklyn Couple

Ladies and gentlemen, Phase Pre-Summer 2017 has officially commenced, and with snow, wind and Netflix & Chill season far behind us, there’s nothing like some warm New York sunshine to spark renewed interest in romantic adventures.

Maybe you’re a guy who’s day-drinking in Brooklyn, spots a pretty young thing in a sundress and thinks to himself, “Damn it to hell, I’d love to take that beautiful lady on a date, but I just don’t know where to go.”

Or you’re a cool New York gal who’s looking to take the reigns on an early-in-the-game date, but aren’t sure how to maximize both the splendor and chill factors. Maybe you’re an established couple who’s over the tedious trips to the corner bar, or you’re doing a little staycation at The Williamsburg Hotel like we did and don’t know the hip spots to check out nearby.

Well friends, fret no longer.

Here’s a Williamsburg date guide straight from the minds of a cool (bias) Brooklyn couple to you. The format breakdown reads as such: Jackson’s picks recommend the rad spots where a lady should take a fella, and Molly’s where a fella should take a lady.

Editor’s note: While we wrote this for our opposite sexes, these places are perfect for every couple to visit. Plus, if we took each other to these spots during ‘the early in the game’ era of our relationship and continue to revisit them as a couple, then they must be worth a visit.

So go ahead, hop on the L train, scout your partner(s) and let’s go.

Written by Molly Tavoletti and Jackson Cook


Photo cred: Molly Tavoletti

Jackson: Pretty Southern

Girls, let’s not beat around the bush here: There is really no reason you need to be the one to impress a guy. That is a task that falls squarely on dudes, whether they are admitting it or not. The orb of power is generally accepted to be held in your beautifully manicured hands. That said, however, there is no reason to not go that extra mile for your main dude, or even for that guy who you woke up next to this morning whose name might be Kevin. (Phil? Bart? No, you would never go for a Bart.) With this in mind, bring your guy to the newly opened Pretty Southern on Bedford Ave. This place is sure to please any self-respecting bro with its wide selection of reasonably priced fried-bird pieces, biscuits as big as a baby and maple doused bacon. And don’t worry, cause the interior is Instagrammable as sin, and they even have gluten-free fried chicken options, so no one is gonna feel that terrible about indulging. BONUS: Since this place is still relatively under the radar, you can enjoy getting a seat right away as hordes of people barely hold back tears waiting for a table next door at Five Leaves.

Photo cred: Molly Tavoletti

Molly:  Cafe Mogador

Five out of 10 brunch “dates” happen when you wake up too hungover to remember how to be a person, next to someone whose last name in your phone still reads just a description of what she was wearing or the name of the bar where you met. You’re really into this girl, and obviously, need some sort of complex carbohydrate to continue living today. But instead of taking a half-block walk for a BEC at the corner bodega and then awkwardly exchanging farewells on the sidewalk, up your game by suggesting a trip to Cafe Mogador. Just down the street from The Williamsburg Hotel (in the event you’re staycationing), this painfully adorable Mediterranean haven will surely impress her need for a cute backyard/mimosa Instagram story, not to mention, you can split a few items and figure out your score on menu compatibility. As a guy, you’ll love this place too because they’ll put whiskey in your coffee if you ask and the cheeseburger changes lives. Pro tip: Get here early. Like, 11 a.m. early (I know, I know). But I promise Bloody Mary’s are even better before noon, and before the young & hungry crowds roll in.


Photo cred: Molly Tavoletti

Jackson: Heatonist

So now that homeboy is all full of fried white meat and biscuit dough, it’s time to take him somewhere that might seem like it’s for him, but it’s really for you. Just a few blocks from Pretty Southern is Heatonist, a store that sells nothing but the best hot sauces from around the country. Right from the first impression of their clever, hot sauce-related puns on their sign outside, your guy is going to be like a kid in a candy store perusing all the colorful bottles of fire that this place has to offer. So why is this place really for you? Because what would a store that sells nothing but hot sauce be without a tasting bar? Just watch him saddle right up to the friendly, black-gloved employee and try one, maybe two sauces before telling them he wants the hottest thing they have. Then stand back and watch as he tries to act like “that was nothing” as his face descends into a red, leaky mess that will leave you crying from laughter almost as hard as he is crying from Scoville units.

Photo cred: Molly Tavoletti

Molly:  Artists and Fleas

Dates don’t always have to involve drinks, you shouldn’t have to order in bars too dark to tell a Bill from a Britney, or expensive nine-course tastings that Dave from work promised as “romantic” but that neither you nor your girl wanted in the first place. So maybe you’re full of brunch and your lady “literally has to — omg — walk off” the meal, but you’re not ready to part ways for your respective subways just yet. So instead of immediately heading to another bar, first suggest you take a stroll through Artists and Fleas. If the girl hasn’t been there yet, she’ll be thrilled to walk around and browse through various vendors selling handmade jewelry and apartment knick-knacks, hoping maybe you’ll secretly buy that necklace she fawned over while she goes to the bathroom. And hey, as a guy, you’ll love it too because you can buy a beanie with Kanye’s face sewn on it, or just gather highly valuable intel regarding her taste─priceless gold you can put straight into your back pocket and save until Christmas/Valentine’s Day/Arbor Day/Tuesday. Ya, girls like gifts.


Photo cred: The Brothers Buoy

Jackson: Full Circle

After he has regained his composure, why not whisk him off to one of the most underrated arcade bars in Williamsburg. The Full Circle bar is just the place to drink away those hot sauce nightmares while you drop dollar after dollar on a fully automated nostalgia machine. The skeeball lanes at Full Circle are always open in the afternoon, and it’s a great place where you can kill a few hours with cheap beer/shot specials and engage in some friendly competition between you and your date. And really, the best thing about skeeball is that no matter what anyone says, no one is good at it. It won’t be like your normal arcade date where you try and play Mortal Kombat but because of his experience from childhood, he is simply untouchable as Raiden. Skeeball is a level-playing field. Enjoy the look on his face when you end up beating him way more times than he beats you. His overconfidence will get him nothing but 10s every time. Oh, and as a total bonus, this bar always crushes the playlist department.

Photo cred: Molly Tavoletti

Molly: Lucky Dog

Realizing you’ve now spent the better part of the morning together, some of which even involved sobriety (wut?), the Brooklyn sun begs to shine down on your joyful consumption of afternoon drinks. But where to? Well, around the corner on Bedford Ave, sits the most suitable day-drinking refuge for you and your girl alike. Lucky Dog allows patrons to bring their furry friends into the bar to join in on the fun, in turn allowing you and your lady to enjoy your libations while parades of puppies greet you with kisses. Not to be presumptuous about gender norms, but girls love puppy, damn it. Some unassuming guest will accidentally aim a painfully endearing pup toward your lady and take this date from zero to heart eyes emoji like that. In the event you’re a dude with a heart made of protein-powered stone and can’t find value in a bar with dogs alone, this place also has a crazy beer + shot deal to keep you going while your gal happily dies of puppy love.


Photo cred: Molly Tavoletti

Jackson:  Antica Pesa

After an afternoon of ridicule, it’s time to bring him somewhere with no tricks or veiled plays to make him make an ass out of himself (but it has been fun, hasn’t it?). Antica Pesa is a world class restaurant that turns the fanciness up to a level just below something that is going to make him wish he went home to change first. The food here is absolutely out of this world, and being Italian, it’s a place where you’re not going to be paying 25 bucks for a plate with three peas and a swipe of sauce on it. The wait staff will make him feel like a king, and you just might walk out of there with a to-go bag of tiramisu that you didn’t order.

Photo cred: Molly Tavoletti

Molly: Allswell

What a day, huh? You did it. You spent an entire day with one girl and survived. But before you start diving too deep into your feelings on monogamy, you’re probably ready to eat again. And when it comes to finding a place to satisfy an equal trifecta of cool, cozy and delicious, Allswell proudly sits smack dab in the middle of the intersection. It’s a beautiful place where time stands still, allowing a moment to bask in your victory over anyone who says dating in New York is hard. Your lady will love the warm wooden walls and the romantic two-person booth at the end of the bar where she can slowly sip the best cocktail she’s had in weeks. And you’ll love it too because if you catch the end of their five to seven happy hour, grab a beer and the best chicken sandwich in Williamsburg for $15 and bask in your dating prowess. Protip: Split the crispy sourdough, a couple Manhattans, and make plans to come back next weekend for brunch.


Photo cred: Molly Tavoletti

Jackson: Bushwick Country Club

Looking in the rearview mirror of this day you two have spent together, riddled with mems, full stomachs, and a couple bottles of wine, you’ll wonder if you can go on. But the “one last drink” after a day like this is where all the magic is going to happen. This place might be a little bit of a trek, but the fact that Uber is a thing throws all excuses out the window. So just tell him that you’re going to take him to the bar where the pickleback was invented and watch him pull out his phone and mash in that address before you have the chance to tell him that there is also mini golf. Be prepared to catch a fainting body at this point, but as long as you can fan him awake, you’ll be on your way to an excellent nightcap at the Bushwick Country Club. A dive bar in the truest sense of the word, you will put a big red check mark in the “she gets it” category after taking him here. And the real kicker of this place: they have one of the last real film photo booths left in Williamsburg. Even after two or three rounds of picklebacks, everyone looks good in this thing. Go home with memories captured on a 2″x8” glossy strip, because your brain stopped recording a couple of drinks ago.

Photo cred: Molly Tavoletti

Molly: Night of Joy

No one asks, “So, should we get another drink?” unless they’re sure the answer is yes. But there’s nothing worse than getting the ‘A-OK’ from the pretty lady you’re into, and then having to awkwardly stall on the sidewalk while you each dive into your respective Google maps, hail mary search ‘bar near me’ and hope you produce something half cool. Or…you could (ahem, should) go to Night of Joy. Your gal will see the flashing ‘cocktails, joy’ neon sign like an endearing beacon, and be instantly infatuated. Inside, the downstairs bleeds cozy romance. Take a seat on an old velvet loveseat, take note of the gorgeous tile below that was made to look like an oriental rug, and order a cocktail tout suite. The beet vodka is a must try, trust me. Upstairs, the roof patio maintains the romantic twinkly lights feel, but with a little more vibrancy. If it’s a nice night, head up the stairs with your drinks, peep the stars, and pat yourself on the back for a nightcap she’ll never forget.

Love all of these spots? See what places this Brooklyn couple goes to by following their Instagrams: MollyTavoletti and TheBrothersBuoy


Written by Molly Tavoletti and Jackson Cook

Feature image via James Bee

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