We do the planning. You have the fun.

Welcome to What Should We Do™, a new personalized planning and booking service in New York City.

Try it Free!

How It Works

  1. Get to Know Your Personal Planner illustration
    Get to Know Your Personal Planner

    One of our professional planners will work with you to understand what you're looking for. Whether it's a night out with friends, a day with the family, or a special occasion.

  2. We Make Recommendations illustration
    We Make Recommendations

    Whether you're a local or in from out of town, we'll tell you exactly where to go in a neighborhood you've never been to, or the perfect place to grab a drink after you've seen what's going to be the next hit show.

  3. We Send You on Your Way illustration
    We Send You on Your Way

    We'll take care of all the details, from making reservations, coordinating transportation, to booking tickets. Your planner will send you a comprehensive, personalized itinerary. And if you need to make changes, or want advice while you're out, we're on call and ready to help.

The Agenda


Arielle Tepper Madover

Arielle is a Tony Award–winning theater and film producer and also the Board Chair at The Public Theater in New York City. Over the years, as a producer, the theater has connected her to the vibrant world of culture and the arts, which she loves to share with friends and family. 

That’s why she founded What Should We Do. Because it’s a big world out there, filled with amazing things to do, and when you go out, you should have exactly the experiences you want. All it takes is a great plan. 

Experience Planner

Amy Rivard

Amy has toured the world singing with shows such as Riverdance and Celtic Woman, and with her eponymous band. However, it was always her dream to live and perform in New York City, which she has been doing for the last seven years. Some of her favorite NYC places include The Bitter End on Bleecker Street, where some of the world’s greatest songs were written, and Washington Square Park to relax and write her own music. She loves checking out the latest and greatest musicals and plays on the Great White Way, and exploring New York’s architectural history.

Experience Planner

Monique Merrill

A self-proclaimed “culture vulture,” Monique enjoys exploring every inch of the city, preferably on foot. She loves the vibrant life of all five boroughs. Monique lives in the West Village with her beagle and dachshund, Buttercup Snoopy and Ziggy Starbucks, overlooking the Whitney Museum! A perfect fit!

Experience Planner

Carolina Ramirez

Carolina, originally from South Florida, has lived in New York City for nearly 10 years. Upon moving to New York, she worked as a commercial and fashion model, appearing in various advertisements and catalogs. Her passion for adventure, travel, and food led her to a career as a concierge, where she was able to share her love and knowledge of New York City. She joins WSWD after several years of working at the Greenwich Hotel and the Soho Grand. She is excited to be able to share with you her inside tips on the best that New York City has to offer! During her free time, she loves cooking, going to concerts, traveling, and pizza! Although her list of favorite pizza restaurants is extensive, she can’t get enough of Paulie Gee’s in Greenpoint!