When Mitchell and Deb were given a second chance at love, their children suddenly had new siblings, but creating new bonds didn't happen overnight.
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On the very last day of March — a month that would prove very important to Mitchell Messinger and Deb Kaplan Jacoby — the couple danced their first dance as newlyweds.
The song they chose was “I Lava You,” from Disney’s 2014 animated film “Lava,” a short played before theater screenings of “Inside Out.” The song tells the story of a patient kind of fairy tale, about a lonely volcano who sits isolated in the middle of the Pacific for thousands of years. Despite his desolation, he remains hopeful that one day he will find his love. What he can’t know is that another lonely volcano has been living just below him under the sea, listening to his song all these years.
Days after she and Messinger shared their first date, Kaplan Jacoby took her son, Josh, to see “Inside Out.” And there in the theater, tears streaming down her face at the sight of two volcanoes defying odds and geology to be together, Kaplan Jacoby recognised a version of her own love story.
But first, there was heartache.
Messinger, 48, a publicity director of ABC Entertainment, was born in Manhattan to Barry and Lynda Messinger. His mother disliked the city, and they quickly moved to New Jersey when Messinger was just six. He attended Syracuse University, where he was for two years the school’s mascot, Otto the Orange. Soon after college, he married Michelle Levine.
I just knew I wanted something more organic. I asked some close friends to start scanning their Rolodexes, which I don’t even think people use anymore.
Messinger and Levine had been married for almost 17 years when, in May of 2014, she died, at 42, of breast cancer. Their daughter, Jillian, was just 10 at the time. Suddenly a single father and grieving widower, Messinger found himself in the midst of the kind of tragedy people whisper about while knocking wood or tossing salt, in the hopes that this kind of loss will somehow swerve around them.
Slowly however, Messinger began to heal. After about a year, he decided it was time to give dating a try. But now with apps and social media to navigate, Messinger found the dating world completely transformed from the one he had first known. “I felt like, OK, I’m not a millennial. I have a child,” Messinger said. “I just knew I wanted something more organic. I asked some close friends to start scanning their Rolodexes, which I don’t even think people use anymore.” Before he knew it, every friend, cousin, and mom at the elementary school his daughter attended was scanning their real or virtual Rolodexes.
Kaplan Jacoby, 46, was born to Dr. Howard and Georgie Kaplan. She grew up in Salt Lake City, and later attended Emerson College in Boston. She is a senior client success manager at CareerArc.
By 2015, Kaplan Jacoby had also decided to give dating a second shot. She had left her marriage in 2010, and was officially divorced from her husband in 2012. Her daughter, Sarah, was eight, and her son Josh, almost five. The separation had been difficult, and Kaplan Jacoby waited years before she was ready to date again. But when she was ready, she was ready. “I went on a lot of dates,” she said laughing, but nothing sparked. “I was ready to swear off dating all together. And then Sharon called to ask if I would be interested in a blind date with a widower.”
Sharon Rosenthal and Kaplan Jacoby met in the 1990s as co-workers and they quickly became close friends. Rosenthal knew Kaplan Jacoby well, but she was hesitant to get involved in any kind of setup. “It made me nervous,” she said. “You don’t want to accept the responsibility if it doesn’t work out. I was just cautious.” But when Ira Sherak, a close friend of Messinger, told Rosenthal that he had an idea about two friends whom he thought might really hit it off, she paid attention. Sherak, after all, had introduced Rosenthal to her own husband. In fact, Sherak has quite the track record as a professional yenta. They couldn’t know it yet, but this would be his fourth setup to result in marriage.
Kaplan Jacoby and Messinger had their first date March 25, 2015. This is a date Kaplan Jacoby can confirm with certainty because she diligently kept a journal entry of each one of the dates she and Messinger shared. Their first date was sushi. Later, they hiked, saw movies, and took small weekend trips away. Both avid Broadway fans (their honeymoon is a Broadway-themed cruise to Alaska, hosted by Sirius XM’s Seth Rudetsky), they attended shows at the Pantages theater in Los Angeles.
One afternoon, Messinger took Kaplan Jacoby to a French restaurant. As she gamely admired the Parisian décor, she asked him if he knew how to say anything in French. “J’adore Deb,” he told her. She asked him what it meant, smiled, but said nothing in return. It wasn’t until several hours later that it dawned on her: He’d just told her he loved her for the first time. Finally, 77 entries later, Kaplan Jacoby decided it was time to stop journaling. She had found her future.
It was also around this time that she and Messinger decided they were ready to introduce their children to one another. Jillian, Sarah and Josh are close in age. Jillian and Sarah, now 15 and 14, even share a birthday. But so much of the close friendship they would eventually develop can be attributed to their grandparents. Messinger remains close with his first in-laws, Stu and Helene Levine, as does Kaplan Jacoby with hers, Marc and Marci Jacoby. All four sets of grandparents attended the wedding. Kaplan Jacoby’s father-in-law even joined them for dinner the night the children met, facilitating new friendships and putting everyone at ease. If it was possible for these complicated relationships to blend together so effortlessly, perhaps they, the children, could as well.
On March 3 2018, Messinger asked Kaplan Jacoby to marry him. It was, by every definition of modern romance, a perfect proposal: at the Four Seasons Hotel Westlake Village, in a Japanese-style pagoda that was reminiscent of their first date. After she said yes, they went to the bar to celebrate and were shocked to find Chris Harrison, the longtime host of ABC’s reality show “The Bachelor,” there to congratulate them. Harrison is a longtime friend of Messinger, and he just happened to be there that night. But for the millions of Americans who watch “The Bachelor,” having the crowned head of professional engagements present seemed like some kind of cosmic Hollywood blessing.
By November 2018, the two families had been living together in Messinger’s house in Bell Canyon, California, for several months when disaster would strike. The Woolsey Fire, which ravaged Los Angeles and Ventura counties, tore through their neighborhood. Of the 10 houses on their street, only three would remain standing. Fortunately, the Messinger-Kaplan Jacoby home was spared. Still, the house was badly damaged, and the family evacuated. (They still have not been given the all clear to return to their home.)
For the first two weeks after the fire, they stayed at Kaplan Jacoby’s father-in-law’s home. They then spent the next two months in a hotel, Josh bunking with Messinger and Kaplan Jacoby, while Sarah and Jillian shared their own room. What had initially been a shy and careful friendship between the girls, quickly became something much deeper. “It was a blessing in disguise because we all became really close,” Sarah said. The experience transformed the trio into siblings.
On Sunday, March 31, almost exactly a year to the day after their engagement, and four years after their first date, Kaplan Jacoby and Messinger wed before 80 friends and family members in a morning ceremony at the Four Seasons Hotel Los Angeles at Beverly Hills. It was one of those beautiful Los Angeles mornings that no one, not even the jaded Californians accustomed to this kind of weather, can resist commenting on. Messinger and a handful of family members and close friends gathered in a small room where he and Kaplan Jacoby would sign the ketubah, the Jewish marriage license, before the ceremony. With an endearing case of wedding morning jitters, Messinger happily hopped around playing the host, introducing those who didn’t already know each other. In his element as this natural hype man, it wasn’t difficult to imagine Otto the Orange in action.
The air was soft and smelled of jasmine as Kaplan Jacoby, wearing a fitted lace gown by DB Studio, strode into the lush courtyard where Messinger was waiting, with his back to her. Smiling, she playfully tapped him on the shoulder. Overwhelmed by the bittersweetness of the day, Messinger was in tears before he turned around. “All good?” she gently checked in with him. “All good,” he reassured her.
As Messinger and Kaplan Jacoby exchanged their own vows, all three children — young teenagers, who only minutes before were making goofy faces to stave off some of the seriousness of the day — wept openly.
“How lucky am I to have a second chance at love?” Messinger asked his bride, friends and family. To which the rabbi quipped, “There’s not a dry eye in the house, Mitch.”