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Two Regulars Get Engaged at Big Daddy's Diner

By Emily Frost | December 27, 2012 8:51am

UPPER WEST SIDE — Jamie Drogin never expected to get engaged at Big Daddy's.

But her fiance Jeffrey Lehman picked the '80s-style diner as the perfect place to pop the question earlier this month, after the couple had one of their early dates there and then became regulars.

"When he actually proposed, I was completely surprised," Drogin said. "Never in a million years did I think it would happen at 9:45 in the morning at Big Daddy."

Drogin, 36, a public relations executive, and Lehman, 38, a real estate lawyer, recently recalled their early date Upper West Side location of New York City-based chain, sitting together in the same booth where Lehman proposed to Drogin on Dec. 8.

"You had the pancakes," Drogin said to her fiance, referring to the summer 2011 date. "I thought it was sort of ridiculous that he got Oreo pancakes." 

Lehman recovered himself when he suggested they order more food: "When he suggested we bring a grilled cheese home, I knew he was the one," Drogin joked.

But it was the shared experience of Hurricane Irene in August 2011 that really set the romance in motion and cemented their love of the diner at Broadway and West 91st Street. They became regulars, and on the one occasion when a line formed outside, they were invited to skip ahead.

"Big Daddy was the only place that was open [during the hurricane]," Lehman said. "We had four meals here that weekend."

"It was the first very concentrated period [of spending time together]," Drogin said.

The couple met online through JDate in June 2011. They moved in together a year after they started dating, with Drogin leaving her Upper West Side neighborhood for Lehman's Midtown apartment.

"I was very upset about leaving Big Daddy's when I decided to move in with him," she said.

The move marked a major shift in their perspectives.

"When we moved in together, we knew we were going to get married," Drogin said. 

A few months later they went ring shopping and Drogin said Lehman then tortured her by keeping her waiting for two months. On every fancy evening out or special occasion, Drogin would be expecting a proposal. 

Lehman said he decided to use Drogin's nephew's upcoming football game on the Upper West Side as an excuse to revisit their favorite haunt in early December.

"She'll never see it coming," he remembered thinking.

Lehman called ahead to sort out the details. He made sure they were seated at a corner table by a window, and he armed the manager with a camera for the big moment. 

That diner's location always had a man making balloon animals, who would come around to the tables to offer them, but Lehman and Drogin always had declined.

For the proposal, Lehman hired balloon artist Melinda Prom to come to the restaurant and offer to make Drogin a special balloon. First Prom made a poodle, then she created a ring — and that's when what was happening started to dawn on Drogin. 

Lehman got down on one knee and said, "Jamie, will you make me the happiest man in the world and marry me?"

People clapped all around them, but Drogin remembers nothing but the question.

"[The moment] was about us even though we were in public," she said.

Glasses of champagne appeared.

Both Drogin and Lehman said they noted early on how "easy" their relationship was.

"We are towards the end of the window of our friends getting married," Drogin said. "I feel like I know myself really well. I don't want to change who I am to be with a person — and we just blend really well together."

"I can find a flaw in everybody," Lehman said. "There was nothing I could point out about her."