“I had never heard of Greg, but then I Googled him and saw this gorgeous guy, with gorgeous green eyes,” said Ms. Grey, a 47-year-old freelance creative director in advertising from Melbourne, Australia.
“I was like, ‘Yeah, set me up, let’s do this,’ ” she said.
But Ms. Grey, by all accounts a rock star in her industry, was given short shrift by a lifelong bachelor whose television career had given him a good measure of fame and fortune, and a predominantly female fan club to go with it.
“He didn’t call,” she said with a sigh, “but I kind of knew why.”
She noted that the introductory email, albeit well-intentioned, provided a fairly “underwhelming” profile of herself.
Mr. Kelly, 48, who said that the email “really undersold Judith to me and did not do her justice,” ran into another mutual friend three months later who offered a much brighter endorsement of Ms. Grey.
This time he did call, and soon after they were on a first date at the Park, a restaurant in Manhattan.
“I sat there and watched this beautiful, stunning woman in a charcoal gray dress walk through the door, she looked amazing,” Mr. Kelly recalled. “We started talking and I realized how sweet and intelligent she was, and we had a lot in common.”
Ms. Grey was equally impressed when she saw Mr. Kelly, who was wearing a gray pinstriped double-breasted suit.
“I liked the way he looked,” she said. “We just sat there talking for hours, easily going from topic to topic, about politics, literature, just about anything, and we understood all of each other’s references.”
“It was this easygoing, wonderful, vibrant evening that you just didn’t want to end,” she said. “And yet I’m thinking, ‘Doesn’t he have to get up at 4 a.m.?’ ”
Two days later, they went for drinks at another Manhattan restaurant, the Red Cat, where they continued moving easily from topic to topic, all the while learning the things that ultimately put them on the road to each other.
Ms. Grey, the youngest of three children born to Eva Menahem, a real estate investor, and Samuel Menahem, a pediatric cardiologist and professor at Monash University in Melbourne, Australia, graduated from the Royal Melbourne Institute of Technology with a bachelor of fine arts degree and received a bachelor of science in neuroscience from Columbia.
Her career began as an artist in Melbourne, where her oil paintings were displayed and sold. She transitioned into the world of advertising, which took her from Sydney to Hong Kong and to New York in 1997, where she became the architect of numerous campaigns for various companies, including Pfizer, Hong Kong Bank and Georgia-Pacific. (She was also a writer, contributing to the Daily Beast and Business Insider, and she wrote and directed the 2003 award-winning documentary “Sin Embargo: Never the Less,” on the resilience of the Cuban people.)
“Judith is simply brilliant,” said Jennifer Pybus, a friend and business partner.
“In the world of advertising, she is formidable, she’s the real deal,” Ms. Pybus said. “She’s elevated and reinvented so many brands for some of the best agencies in the world. She somehow knows what people want before they even know they want it.”
Ms. Grey, who no longer had a need to look up Mr. Kelly online, learned firsthand that he was the son of Veronica and Raymond W. Kelly and had grown up in Garden City, N.Y. His father, also a former Marine, served two stints as New York City police commissioner.
Mr. Kelly graduated from Fordham University with a bachelor’s degree in political science and went on to serve nine years as an attack pilot in the United States Marine Corps, specializing in flying the AV-8B Harrier jet. During his service, Mr. Kelly amassed 158 aircraft carrier landings and flew over Iraq in Operation Southern Watch, enforcing the United Nations-imposed no-fly zone.
“Greg was a bit of a maverick back then,” said Ossen D’Haiti, a fellow Marine pilot and longtime friend who served with Mr. Kelly in the early 1990s. “He’s the kind of guy you want in your squadron. He doesn’t get too uptight, and finds levity in everything he does.”
Mr. Kelly’s news job took him back to Iraq, where he provided extensive coverage of the war, including four long-term assignments in Baghdad. During the 2003 invasion, he was embedded with the Army’s Third Infantry Division, Second Brigade, and was the first television reporter to follow American forces infiltrating Baghdad as they stormed Saddam Hussein’s presidential palace.
During that particular battle, Mr. Kelly was wounded, struck in the face by shrapnel.
“My wife and I were watching it on the news, and there was Greg, a world away, just lying on the ground, motionless,” Raymond Kelly recalled. “All we could do was just hold on to each other and pray.”
Mr. Kelly’s injuries proved minimal, however, and he was “out of action for about half an afternoon,” as he put it.
There were other challenges for Mr. Kelly, however: In January 2012, he was the subject of a very public sexual assault claim in Manhattan; after a two-week investigation, prosecutors decided not to file charges.
Mr. Kelly, a licensed commercial pilot, later went on to achieve the rank of lieutenant colonel in the Marine Corps Reserves, which he left in 2014.
“He’s a Marine, like his father was, like I was,” said the former Mayor David N. Dinkins, a longtime family friend. “Just a rock-solid, respectable young man.”
Ms. Grey and Mr. Kelly turned a serious corner on their third date, when he took her to a brunch in West Point, N.Y., then surprised her by driving to his family’s 40-person Christmas party in Breezy Point, N.Y., where she met his parents, as well as his brother, Jim Kelly.
“She couldn’t believe he took her to meet his family so early in their relationship, and she absolutely loved his parents,” Ms. Pybus said. “That’s when she told me, ‘This is different, this is it.’ That’s when she knew.”
The former police commissioner, who, at times, playfully interrogated his son about settling down, had a hunch that Ms. Grey was in their lives to stay.
“Judith is a beautiful, amazing, multitalented individual,” said the elder Mr. Kelly, who served as New York’s top cop from 1992 to 1994 under Mr. Dinkins, and again, from 2002 to 2013, under Mayor Michael R. Bloomberg.
“She spent a lot of time with us this past summer and we really got to know her and realized that she and Greg are in perfect sync with one another, two hard-working people with a great sense of humor,” he said. “As far as Veronica and I are concerned, she’s the daughter we never had.”
Greg Kelly said that as his relationship with Ms. Grey deepened, he would often asked himself, “Why haven’t I met this person before?”
As it turned out, he almost had.
“After much triangulation, I eventually realized I had actually seen Judith months before being introduced to her,” Mr. Kelly said. “I was in Sag Harbor, and I noticed this beautiful woman stretching and jogging at the dock, but she was wearing earphones, which I took as a sign that she didn’t want to be bothered.”
“I had just finished working out at a gym there and was standing some distance away, but it was definitely Judith, who has a place out in Sag Harbor,” Mr. Kelly said. “I actually went back the next day to see if I would see her again, but she wasn’t there.”
Though he eventually caught up to her, Mr. Kelly would lose Ms. Grey again in March of this year. They split up that month. The inevitable talk of marriage put a strain on their relationship.
“He was nervous about committing,” Ms. Grey said.
Mr. Kelly did not disagree.
“There was some pressure, certainly a little bit of ‘Am I ready?’ that sort of thing,” he said. “But there were other things going on at the time, it was complex.”
After nearly seven months apart, they began talking through some issues and came to realize that they were meant to be.
“Judith is the love of my life,” Mr. Kelly said. “From the first time we met, I knew she was good for me.
“She is brilliant, beautiful and giving,” he added. “She has taken care of me and brought real stability to my life.”
They reunited, and were engaged on Labor Day. “Our getting back together was our engagement,” Ms. Grey said. “When I look at him, I still see a man constantly grappling with how to be a better person, but he’s very warm and caring, and he has an encyclopedic mind and a real sense of consciousness.”
They were married at the University Club of New York on Nov. 12, where the cocktail reception was also held. Mr. Dinkins led the ceremony, a first marriage for both, which did not include religious traditions (the bride is Jewish and the groom is Roman Catholic).
“You must always remember that it is rarely the great things that destroy a home, it is more often the small things,” Mr. Dinkins told the couple and their 200 guests, including François Delattre, the permanent representative of France to the United Nations in New York, John Catsimatidis of supermarket fame and Rhona Graff, President Trump’s longtime executive assistant.
“So that each of you take care of the small things,” Mr. Dinkins said, “then together you can defend your home against the great things.”
When asked what kind of man Ms. Grey had exchanged vows with, Ms. Scotto said without hesitation: “Judith is marrying a man who was like a brother to me, a man who brought sunshine, laughter and just the unexpected to my world every morning for almost 10 years, a man I really miss.”
But she doesn’t miss taking calls about him.
“My phone would ring constantly with women asking about Greg,” she said. “All I kept hearing was ‘Is Greg available?’ Is Greg still single?’
“Now I can happily say, ‘He’s off the market ladies, back off.’ ”