Ask Ari

Ask Ari: How Fried Chicken and Selfies Can Bring Two Sisters Together

For the debut of our new column, WSWD's founder solves a planning problem with help from Sweet Chick and Dream Machine.

Photo courtesy of @fomofeed

New York City famously has no shortage of incredible places to visit, art to see, food to try, and experiences to be had. But finding the right places to visit, art to see, and food to try with your family and friends—or blind dates or colleagues or your kids’ classmates—is something else entirely. (That “something else,” as you’ll soon see, often involves fried chicken and selfies, but we’re getting ahead of ourselves.)

That’s where Arielle (Ari) Tepper Madover comes in. A lifelong New Yorker, a Broadway producer, and founder of the in-the-know planning and recommendation company What Should We Do?! (that’s us!), Tepper Madover has been the go-to person for plans in her social circle for years. Looking for anniversary ideas? Want to suss out the perfect night with your old college friends? Single and solo this weekend? Just ask Ari! Send your burning planning questions to Problem solved.

In this debut column, Ari helps two sisters reconnect over fried chicken and selfies.

Hi Ari,
My sister is visiting me in NYC next month from St. Paul, Minnesota. We haven’t seen each other in three years! I want to plan a day that’s special and unique, but also gives us the chance to talk and reconnect. Any ideas?
—Ella in Brooklyn

Hello, Ella! How wonderful! Treat your sister to a day in a fun and funky, uniquely New York neighborhood: Williamsburg.

Start the afternoon with a brunch of to-die-for (and to-lie-down-for when you are done) fried chicken and waffles at the local and celebrity favorite, Sweet Chick. Then walk over to  Dream Machine, a quirky and interactive sort-of grown-up playground where each room has a different dream-inspired theme. (This photogenic spot is made for Instagram, so you’ll get plenty of sister selfies here!) Next up: shopping at Artists & Fleas, just two blocks away, where local artisans sell their handmade, one-of-a-kind art, jewelry, bath products, home accessories, and more. It’s like a stylish yard sale! 

Depending on how much time you have, there’s so much more you can do in the immediate neighborhood: Get homemade ice cream at OddFellows; play a few frames at the lounge-y Brooklyn Bowl; walk through McCarren Park; catch an indie movie at Nitehawk Cinema; sip cocktails and take in the sweeping city views at the rooftop bar Westlight; and pop into all the cool shops along the way. I don’t have any siblings, but I love casual, figure-it-out-as-we-go, stroll-and-chat days with my friends. Enjoy!

Do life well,

Want us to create a special day for you? Get in touch with one of our experience planners now, or write to Ari at