To James Arthur Dolce, the possibility of crossing paths with Ashley Lee Tyrner was, as he put it, a “one in a million situation.” After all, they lived 3,000 miles apart.
In reality, however, the two were orbiting the same circles before they even met. They discovered that they had each been dining at the Mandarin Oriental, the luxury hotel in Manhattan, during a neighborhood-wide blackout on July 13, 2019.
It was three months later, in October, at an event hosted by angel investors at the rooftop restaurant of RH New York, a large building owned by Restoration Hardware, that they met for the first time.
Ms. Tyrner is the founder and chief executive of FarmboxRx, which works to eradicate America’s food deserts by shipping produce directly to members’ doors. At the time, she was in the process of developing her go-to-market strategy for the health care division of her company by partnering with private insurance companies and Medicaid and Medicare programs.
Its mission is personal to Ms. Tyrner: When she moved to New York from Arizona in 2011, she initially relied on food stamps to support herself and her then-infant daughter. Her previous marriage ended in divorce.
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Once she began talking to Mr. Dolce, a philanthropist and founder of multiple tech companies who was then living in San Francisco, they clicked. Ms. Tyrner had a date scheduled for later that night, but she canceled it to join Mr. Dolce, who goes by Jim, for tacos after the event. Over dinner, she shared the idea for the health care division, something she had been keeping quiet for fear that others might copy her idea.
“I didn’t want to stop talking to him,” she said. “From the moment I met him, I knew I was going to marry him.” Ms. Tyrner later called her best friend with the news that she had met her future husband.
Mr. Dolce, whose previous marriage also ended in divorce, took longer to develop romantic feelings. “I enjoy talking business, particularly to entrepreneurs,” he said. “I just took that conversation as a typical coaching discussion.”
Mr. Dolce, 62, grew up in Johnston, R.I., and holds a bachelor’s degree in computer engineering from the University of Rhode Island. He is currently the chief executive and chairman of the board of directors at Lookout, a mobile security software maker. He has two sons, ages 27 and 30, from his previous marriage.
Ms. Tyrner, 40, grew up in Casa Grande, Ariz.
The two didn’t meet again until Mr. Dolce returned to Manhattan the following month. It wasn’t until he eventually kissed Ms. Tyrner on their fifth date that she was sure of his intentions. “All he would talk about was business stuff with me,” she said. “So I’m like, ‘He either wants to steal my idea, or maybe he wants to be my investor.’”
Ms. Tyrner said she “was very much attracted” to the fact that he was also an entrepreneur who “has a big heart.”
Mr. Dolce said he first fell for Ms. Tyrner’s “beautiful smile.” Moreover, he said, “She is self-made and fiercely dedicated, but she is warm at the same time. She is an incredible mother.”
By early 2020, the pair’s relationship had grown more serious. Then, the pandemic hit. Along with her daughter, Ms. Tyrner — who said she was previously “the New York woman that is never leaving New York” — spent the spring and summer of 2020 with Mr. Dolce in San Francisco before the trio relocated to Boston. In October 2022, Mr. Dolce proposed in Florida on the couple’s boat, Restoration, named after the company behind the event where they met.
On June 15, Ms. Tyrner and Mr. Dolce wed in Lake Como, Italy, before nearly 100 guests. Ms. Tyrner’s daughter, who is now 13, walked down the aisle with Mr. Dolce’s sons. John Hering, a friend of the couple and executive director and founder of Lookout, officiated; he obtained a one-day marriage designation through the state of Massachusetts for the occasion.
During the wedding, Ms. Tyrner was giving a speech with her stepbrother, Kyle Smith, when the power went out for a brief period. The couple considered this a meaningful sign that hearkened back to the July 2019 outage they both experienced at the Mandarin Oriental.
The Monique Lhuillier dress that Ms. Turner wore for her wedding welcome party featured small blue butterflies. She found the metamorphosis that the insects undergo to be a fitting metaphor for what lies ahead. “I feel this relationship represents my rebirth and evolution to my next chapter,” she said.
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