Like so many New York singles, Ms. Walzer kept a precise mental inventory of what she wanted in a mate. He should be entrepreneurial, like her; he should be Jewish, as she is; and they should share goals and values, including a devotion to family. And, oh yes: “I didn’t want him to be more than three or four years older than me,” said Ms. Walzer, now 36 and the owner of an online data storage business called Backup My Info!

She and her list underwent a severe test when she met Mr. Berkowitz almost 11 years ago on JDate. Mr. Berkowitz was Jewish, a University of Pennsylvania graduate with an M.B.A. from New York University. And he was also very close to his family.

The couple went out twice.

“She was great, beautiful, bright,” Mr. Berkowitz said. “I always thought she was a great catch — down to earth, very sweet.”

Ms. Walzer said she “had a blast.”

But he was nine years older than she was.

So after their second date —a Squeeze concert — she called to thank him and tell him that he was too old.

“I had just moved to New York from Atlanta,” she said. “I was a very immature 26-year-old.”

Mr. Berkowitz, who grew up in Woodmere, on Long Island, was taken aback. “I was kind of shocked since we had two amazing dates, and my age hadn’t changed since she first met me online,” he said.

They stayed in touch over the next few years, calling on birthdays, running in the same social circles, going out for the occasional drink.

She would often grumble about her love life, and Mr. Berkowitz was flummoxed. “I was just not getting it,” he said. “She was complaining about all the guys she dated — this one’s a geek, that one’s not treating her well. But she still went out with them.”

All the while, Mr. Berkowitz was enjoying the life of a New York bachelor. He was a “serial dater” as several friends put it, sometimes having a lunch date, a dinner date and a drink date, too, the same day. In fact, he decided to share his dating experiences, and 10 years ago began writing a book on the subject. A year ago, “The 21st Century Guide to Bachelorhood: Lessons Learned Over the Past 20 Years,” was self-published.

He had no problem meeting women, but added: “There was a quality I was looking for — the kindness, the smile, the intelligence, the ‘get it’ type. They didn’t have that.”

Their friends often wondered what was going on between Mr. Berkowitz and Ms. Walzer.

“I’d hear about this Jennifer and say, ‘Why aren’t you dating?’ ” said M. J. Pedone Needleman, who has known Mr. Berkowitz for 10 years. “I believe it was a timing issue.”

One of Ms. Walzer’s best friends, Julia Fagin, said Ms. Walzer’s reluctance was about identity. “Jen wasn’t ready to deal with boys until she stood on her own two feet,” Ms. Fagin said. (Indeed, Ms. Walzer, who now contributes to a business blog for The New York Times, emblazoned the words “CEO 2 BE” on her cap when she graduated from the University of Arizona, and on the license plate of her convertible.)

When Ms. Walzer joined the matchmaking group It’s Just Lunch in 2006, they told her that her top match was a fabulous man named Brad. “Brad Berkowitz?” she asked. “How did you know?” the startled voice on the other end asked.

In 2008, she joined JRetromatch.com, and soon received an e-mail message describing an ideal mate they had for her. His name? You probably can guess.

Ms. Walzer and Mr. Berkowitz laughed about it but made no plans to date.

Toward the end of summer 2007, Ms. Walzer, Mr. Berkowitz and other friends ended up sharing a summer house in the Hamptons. They spent many hours telling dating and relationship stories. One night, Ms. Walzer and some others went to a nightclub. When a friend became sick there, she called Mr. Berkowitz for a ride back to the house. His genuine concern and generosity in that moment suddenly shifted her perception of him.

“I always knew he was a great guy,” she said. “I just never looked at him other than a great friend.” Later that night they decided to go out on another date in the fall.

But not long after that, Mr. Berkowitz lost his Wall Street job and had shoulder surgery. When he finally felt able to pursue Ms. Walzer, she had already met someone else.

“I was sad, but for some reason I still didn’t think it would work out,” he said of that relationship. “So I thought that by checking in every couple of weeks, she would still know I was still there.”

The relationship did end. He said he told Ms. Walzer: “You complain about all these guys you date. Why don’t we go out? This is ridiculous.”

So, in March 2008, nine years after their second date, they finally had their third at a French restaurant on the Upper East Side. Soon they were very much a couple and by July they were in love. And last May, they became engaged. In September he began heading the sales department of Lock Your Docs!, another company of which Ms. Walzer is an owner.

They were married on Jan. 9 by Rabbi Anthony Fratello at the Polo Club of Boca Raton in Florida before 175 guests, many of whom were shivering in unseasonably frigid weather.

“I met a lot of girls and dated a lot of girls, but they were all missing something,” Mr. Berkowitz said.

“She was definitely worth waiting for,” he added.

The bride said she could not believe she wasted more than 10 years without him.

“I look at him now and he’s the hottest guy on the planet,” she said.

And at the top of her list.

 

~New York Times