A Kiss in 1998. A Date in 2007. A Wedding in 2020.

After seeing Jennifer Miles in a bikini in 1998 while mowing her father’s lawn on Lake Wawasee in Indiana, 15-year-old Nate Goldenberg was confident enough to ask her on a date. “I was 100 percent in love,” said Mr. Goldenberg, now 37, and the general manager of Grand Design RV in Elkhart County, Ind. “Her dad said yes so we went to a party and found that we had mutual friends. I really wanted to date her.”

Ms. Miles, also 37, remembers what a great time they had that night, but her family lived most of the year in Kokomo, Ind., and she was dating someone else. “Nate and I hit it off and even shared a kiss that summer but nothing developed,” said Ms. Miles, a former insurance executive and stay-at-home mother to her two children from a previous marriage. Mr. Goldenberg also has a daughter from a previous relationship.

After high school, Ms. Miles studied for a degree in public affairs from Indiana University while Mr. Goldenberg took some business courses in Fort Wayne, but he said, he “hated school.” He began selling cars before transitioning into the recreation vehicle industry and investing in fitness gyms. (In 2016, while he was a minority owner in Grand Design RV, the company was sold to Winnebago for $500 million.)

Since Mr. Goldenberg and Ms. Miles remained part of the same group of Lake Wawasee friends who gathered most summers, and she underwrote the insurance for his investments, they kept in touch. But nothing happened until 2007. “Nate asked me to dinner at Sullivan’s Steakhouse in Indianapolis, bought a $150 bottle of Cakebread Wine and pulled out my chair,” Ms. Miles said. “He was such a gentleman. Nobody had ever given me such a fancy evening. I knew he wanted romance but he was working in San Diego.”

Mr. Goldenberg added: “She was so smart, interesting and fun to hang with that I decided to never give up on her because other girls bored me. I just had to figure out how to win her over.”

The following year, Mr. Goldenberg flew Ms. Miles and her best friend to San Diego for the weekend. Yet, even after fun dinners there was still no romance. “I was dating the guy I would eventually marry and while I was very fond of Nate he had been a wild man when he was younger,” she said. “I worried about a serious relationship with him living so far away.”

They didn’t reconnect until the end of 2017 after Ms. Miles divorced, and Mr. Goldenberg had an insurance policy up for renewal. After a romantic working dinner followed by weeks of texting, Mr. Goldenberg learned that Ms. Miles would be in New Jersey for a woman’s leadership conference, and devised a way to join her.

“Nate said he had business there but I didn’t believe it,” Ms. Miles laughed. “But the chemistry was there, and the relationship took off like wildfire. I felt he had matured. I loved his sense of humor and soft heart for such a strong man.”

In December 2018, Mr. Goldenberg proposed at their winter home in Granger, Ind. They planned a May wedding for 300 guests at the Ocean Reef Club in Key Largo, Fla., a private community where Ms. Miles has a family home. But it had to be postponed for five months because of the coronavirus. Finally, on Oct. 23, the Rev. Michael J. Calderin of St Jude Ministries in Pembroke Pines, Fla., officiated before 120 guests at Ocean Reef.

“Even with the stress of changing the wedding date Nate was so thoughtful, kind and caring,” Ms. Miles said. “With my Type A personality, I needed someone strong. And seeing him so excited and involved with our daughters, I have grown to love him more each day.”

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