An Almost-Missed Connection Saved By a DM

After matching on several dating sites in 2017, Joseph Michael Flaum was becoming increasingly interested in Allison Dana Port. She was feeling overwhelmed, however, not by Mr. Flaum but the barrage of messages she was continually receiving through the apps.

So, when Mr. Flaum, 38, sent Ms. Port, 35, a message, she didn’t respond.

Then, in the early fall of 2019, they matched again. Mr. Flaum still received no response to his message to her. But he wasn’t giving up, deciding instead to contact her through Facebook.

This impressed Ms. Port and messages were exchanged. Their first date on Oct. 15 was at the St Tropez Wine Bar and Restaurant in the West Village near their apartments, which happened to be just a few blocks away from each other.

“We must have crossed paths,” Mr. Flaum said, “but it was more like ships passing in the night.”

Mr. Flaum came into Ms. Port’s life at a crucial time. Her father had been diagnosed with pancreatic cancer that summer. “I couldn’t imagine having gone through that without him,” she said. “It was like a gift sent from the universe.”

Then Covid struck, and when Ms. Port got the news that her father’s cancer had progressed, she decided to return to her family home in Woodbury, N.Y.

Mr. Flaum also went home to Boca Raton, Fla., to spend time with his family. He bonded with his nieces and nephew while continuing to grow his connection with Ms. Port. Both returned to the city around Memorial Day 2020 but traveled back to their hometowns often. The summer provided a bit of a respite.

During that summer, Ms. Port took Mr. Flaum home to meet her family. Ms. Port’s father took a liking to Mr. Flaum and, before they left, her father pulled her aside. “At this point, I think my dad maybe knew he didn’t have a lot of time and he wanted to make sure I knew that he loved Joe.” He told Ms. Port that Mr. Flaum had his blessing, should they decide to get married.

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Back in the city, winter was approaching. And when Ms. Port’s father died on Oct. 25, 2020, the pair wanted an escape. “We were ready to take a break and get some fresh air,” Mr. Flaum said, so they decided to spend the winter skiing and working remotely in Aspen, Colo.

But first, a stop in Florida to see Mr. Flaum’s family for Hanukkah. He watched as Ms. Port embraced his nieces, sometimes holding a girl in each arm. “That was when I was like, ‘Oh, this could be it.’”

The couple stayed in Aspen for “four blissful months” and skied until the final days of the season in T-shirts. They then spent another year in the city, living in a new place in the West Village together.

Ms. Port has a bachelor’s degree in public affairs from Indiana University. She is a senior account executive at Amazon, working in digital advertising sales. Mr. Flaum received a bachelor’s degree in finance from the Wharton School of the University of Pennsylvania and is a senior analyst and technology, media, and telecommunications sector head at SPX Capital, a hedge fund.

While the couple was on a ski trip with friends in Switzerland in December 2021, Mr. Flaum planned a surprise. At the mention of a code word — a certain stock ticker — Mr. Flaum’s friend pulled out a camera to capture his mountaintop proposal.

The couple were married Dec. 3 by Rabbi Jonathan Tabachnikoff of Congregation Dor Chadash at Playa Largo Resort and Spa in Key Largo, Fla., before about 150 guests. The ceremony was held on the beach.

The pair included some updated Jewish traditions. “We’re doing the seven circles,” Ms. Port said and described a wedding ritual where a woman walks around a man seven times, “but we’re splitting it and we’re each walking three times around each other and then one time together.”

There were many speeches at the rehearsal dinner but only one at the reception. “I am very lucky that my dad actually wrote a wedding speech before he passed away,” said Ms. Port, who will be taking her husband’s name. Her older brother, Billy Port, read her father’s speech.