Once Mr. Caneco responded, he displayed what she considered a weirdness of his own: After only a few messages, he asked to switch to phone calls. “I’m somebody who only talks on the phone for work,” she said. Overcoming that aversion for Mr. Caneco seemed worth it, though. His devotion to Beanhead, whose mystery illness was never diagnosed before his death at the end of 2020, was part of it. So were his messages, which rung sincere. “There was nothing off-putting about him,” she said, including his background.

Born on Staten Island, Mr. Caneco joined the Navy in 2005 after earning a bachelor’s degree in history and Middle East studies from Fordham University. He was a naval flight officer until 2013, completing two combat deployments, and then served as a reservist until 2016 while he was in law school at Seton Hall University. He received a Master of Laws degree in taxation from Georgetown. Ms. Hilton happened to be a passionate follower of air travel stories. “I do have a morbid fascination with commercial aviation disasters,” she said. “But I was obsessed with tracking planes in general.”

A week or two after their first phone call, they migrated to video chats and the miles between them became meaningless. On weekends, they would share their screens and watch movies together, including the filmed version of the musical “Hamilton.” By August 2020, she was ready to take a leap of faith. “I decided I need to break out, Covid be damned, and go to New York City to meet him,” she said. She didn’t tell her family. “I think I told one colleague, ‘If I go missing, please avenge my death,’” she added.

Instead of falling off the face of the earth, she fell in love. After a first date on Aug. 28, 2020, at Chama Mama, a restaurant in Chelsea, they went back to her hotel and hung out on the balcony, tracking flights on her phone app. Love took wing for both that night. “I remember thinking, there were no differences, no issues in person,” Mr. Caneco said. “I wanted to move the ball forward.”

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