New York Observer

Kenneth Sugarman and Bonnie Winston

Met: Memorial Day weekend, 2001

Engaged: Dec. 13, 2001

Projected Wedding Date: May 11, 2002

By day, Bonnie Winston runs Winston West, a glamorous bicoastal photo agency that represents fashion and celebrity photographers. By night-she’s a yenta !

Everywhere she goes, Ms. Winston who is blond and bubbly, keeps a running tab of her friends’ and acquaintances’ vital statistics, scribbling them down in a little red appointment book.

“I talk to everybody ,” she said. Recently, she bragged, she sidled up to Sex and the City actor John Corbett at a bar and hooked him up with a work pal of hers, a fashion model named Krista Cassidy.

Last Memorial Day weekend, a friend of Ms. Winston’s dragged her out to East Hampton, hoping to get a piece of that matchmaking action. They went to a place called the Grill. “My whole theory is, go somewhere that used to be trendy,” said Ms. Winston. She was munching on a cheeseburger and fries when she glanced to her left and noticed an attractive older man in sweat pants and loafers, sipping a white-wine spritzer.

“How about that guy?” she asked her friend.

“Why don’t you like him?” her friend asked.

“He’s a little Robert Blake–ish,” she said, “and my name is Bonnie.”

But she struck up a conversation nonetheless and learned that his name was Kenneth Sugarman, that he was a perfectly respectable general-practice lawyer specializing in civil litigation, and that he was in the Hamptons helping his daughter from a first marriage celebrate her graduation from Manhattan’s Trinity School.

When they met the following Thursday at Balthazar, Ms. Winston was pleasantly surprised.

“He really cleaned up well,” she said. “I thought him more Robert Downey Jr. than Baretta.”

Make that Mike Brady: Mr. Sugarman, a lawyer told her almost immediately that he wanted to remarry and have more kids. Phew .

Months later, the pair was snuggling together in his Noho loft, watching the final round of Jeopardy . The category was U.S. Presidents. “This man,” said Alex Trebek on the TV, “was elected Vice President twice and President twice.”

Naturally, it was at this moment that Mr. Sugarman turned to Ms. Winston and proposed.

Her response: “Yes! Nixon!”

(Hey, she forgot to put it in the form of a question!)

“I never get Final Jeopardy right, so I look at it as a sign,” she said. “I was so excited that I knew the answer that I couldn’t let it go. I’m a really big multi-tasker.”

That same night, she set up two close friends and they all went out on a double date.

– Blair Golson