While Ally Shapiro was taken by surprise with her engagement to Jordan Bilfeld, her mother, Real Housewives of New York City alum Jill Zarin, had already known about the proposal but was unsure of when it would happen.
“For seven months, I kept the secret,” Zarin told PEOPLE in an exclusive interview.
Bilfeld had sought Zarin’s approval months before, but as the days passed, she started to wonder if he might have changed his mind. During a recent family cruise through Europe, she even shared her concerns with Shapiro, admitting that she was beginning to doubt if it would ever happen.
Shapiro’s engagement ring steals the spotlight in her Instagram photos, marking a special milestone
“We were having a heartfelt conversation on the second-to-last night of the cruise,” Shapiro told PEOPLE. “For the first time, my mom said, ‘You know, Jordan’s been telling people he’s going to propose this summer, but he hasn’t yet.’ I asked her why she thought that, and she replied, ‘Well, he asked for my permission seven months ago, and he still hasn’t done it.'”
What Zarin didn’t realize was that Bilfeld had planned to propose the very next day.
“I didn’t want to give away exactly when I’d pop the question,” Bilfeld explained. “I knew the cruise would be a perfect backdrop, visiting places like Rome, Corsica, and Barcelona, so I thought it would be a great moment to propose at the end of the summer. But I kept the timing a secret.”
After months of careful planning, Bilfeld was ready to execute his proposal despite an accidental slip from Zarin the night before. “I had everything worked out,” Bilfeld shared with PEOPLE, “but Jill let something slip right before.”
“The whole evening became chaotic, and the next morning I had the ring in my pocket,” Bilfeld recounted. “Then Jill’s boyfriend, Gary, starts chatting with me. He said, ‘You haven’t proposed yet, summer’s nearly over. What’s your plan?’ Nobody had any idea the proposal was happening on that trip.”
The following day, after a relaxing lunch by the beach in Mallorca, Bilfeld asked Shapiro to walk with him to a pool with ocean views, where he finally proposed.
“As he started talking, I completely froze,” Shapiro recalled. “I wasn’t dressed up—just a cover-up, no makeup, and my bathing suit. We had just finished lunch, and suddenly he’s asking, ‘Will you marry me?'”
Shapiro described the moment as “absolutely beautiful.” The special occasion was captured on camera, thanks to Bilfeld arranging for a photographer he found on social media to discreetly take photos.
With a stunning 5.25-carat platinum and diamond ring designed by Joey Alibayof of Alexa Trading, Bilfeld pointed out the hidden photographer after the proposal.
“And then the whole crowd started clapping,” he laughed. Shortly after, Zarin and Gary arrived, completely unaware of what had just occurred, as they had been occupied with paying the bill. Zarin, confused by the applause, soon spotted her daughter. “I looked over the balcony and saw Ally. I freaked out, of course, and we rushed down,” Jill recalled.
Back on the cruise ship, Bilfeld had another surprise: their room had been decorated with balloons and champagne. The celebrations didn’t stop there, as Bilfeld had already arranged an engagement party back home in the Hamptons for Labor Day weekend.
“I was blown away,” Zarin said. “Not only did he make the engagement so special, but he also planned a party in the Hamptons, with his family flying in from Florida. Everything was taken care of.”
As they begin planning their wedding, the couple shared with PEOPLE that they envision a celebration with around 300 guests. In the meantime, Shapiro has been enjoying her engagement, sharing Instagram photos of her dazzling diamond ring.
