Modern Love Story + Vintage-Inspired Jewish Wedding in New York City

Haley Draznin and Jason Leibowitz

Photographed by: Joanna Toto for The Day by Ira LippkeLocation: New York City, New York, United States

It’s surprising how long it took Haley Draznin and Jason Leibowitz to meet, but serendipity did eventually bring them together. While attending the wedding of a family friend, Haley’s brother introduced her to a man he played tennis with in college. That man was Jason, who happens to be the groom’s cousin. As he and Haley talked at the reception, they were amazed to discover they lived in the same apartment complex in Manhattan, only two floors apart. “We shared a cab ride home together, exchanged numbers, and would later run into each other in the building’s elevators in the months following with flirtatious hellos,” Haley reveals. 

If not for a friendly doorman named John and an extra slice of pizza, it might never have gone beyond that. Haley got to know the older gentleman due to her early hours working at the CNN newsroom. One night Jason arrived home and offered John his extra slice. As they chatted together, Jason mentioned he was looking for someone special. “There’s a girl named Haley in the building that is wonderful,” John told him, and Jason quickly realized this was the same woman he had met at his cousin’s wedding. Inspired to reconnect, he asked her on a date. 

Their relationship strengthened over the years, and Jason knew it was time to take the next step. “We were in love and I realized she was my best friend,” he muses. After taking Haley’s father out to dinner to get his blessing, Jason met with a family friend, Jack Solow of Solow & Co. in order to create the perfect ring for his sweetheart – thanks to some hints she had provided regarding her style. 

A trip with his family to St. Barths seemed like the ideal opportunity to propose. “However, since Haley is very close to her family I knew that wherever I proposed they would have to be there,” Jason notes. He arranged for her loved ones to make the trip as well in order to create the perfect celebration. During a walk on the beach at sunset, Jason got on one knee and asked Haley to be his wife. A photographer captured the moment, and soon after the family of the bride-to-be emerged to surprise her. 

There was no question as to where the wedding would be held. “We are New Yorkers through and through,” Haley confirms. “We wanted to evoke a vintage, old-school New York City theme to highlight our modern love story.” They commissioned a New Yorker cartoon artist for custom save the dates, along with formal invitations embossed with silver by Ceci New York to alert the prospective guests of the March nuptials. In honor of the groom’s French-Moroccan heritage, the couple had a Moroccan henna ceremony in the months leading up to the wedding. 

When the big day arrived, friends and family walked into the venue located beneath the Queensboro Bridge and featuring a canopy of tile vaults, making for a unique setting. The wedding party arrived on a white trolley to the indoor ceremony awash with warm lighting, though the night sky could be seen through the windows. The Jewish service was conducted underneath a stunning chuppah with lush ivory florals and cascading crystals. 

Following the vow exchange, the newlyweds joined their loved ones in an elegantly decorated space filled with elaborate centerpieces of calla lilies and orchids. “The wedding floral design was a crisp and clean white – we added crystal balls and lights throughout to modernize it,” the bride details. A dance floor with a large black-and-white checkered pattern was filled all night long as the live band performed music selected by the groom. Additionally, Jason surprised his new wife by joining the band onstage to play “Clocks” by Coldplay on the keyboard, which was Haley’s most memorable moment of the wedding. 

Neither bride nor groom would change anything about their perfect day, but Haley does advise couples to be present and take everything in during the celebration. She reflects, “It’s so rare that all your loved ones are in the same room at the same time.”