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From the First Date, Looking the Part of Husband and Wife

On their first date, at a Manhattan wine bar in May 2016, a waiter mistakenly referred to Michael Angelo McMillan II as Caroline Benning Hubbard’s husband.

“I didn’t have any rings or anything that would indicate that we were married,” Ms. Hubbard said, but “the chemistry that we had just sort of indicated we looked like we were a married couple.”

Other patrons at the bar also noticed their connection. As they were leaving, a man who had been sitting next to them leaned over to tell them they were a beautiful couple, and asked how long they had been together.

“And we were like, this is actually our first date,” Mr. McMillan said.

The two had met in San Francisco a month earlier, in April 2016, when they bumped into each other at a bar as Ms. Hubbard was leaving and Mr. McMillan was arriving. They began chatting and learned that they were both juniors in college at the time — Ms. Hubbard at Harvard and Mr. McMillan at Vanderbilt — who had come to San Francisco on their spring breaks to attend a conference hosted by Management Leadership for Tomorrow, an organization dedicated to fostering more diverse and equitable workplaces.

“He just seemed so genuine, I just wanted to get to know him,” Ms. Hubbard, 27, said.

“It was very serendipitous,” Mr. McMillan, 27, said.

They also learned that they had friends in common, and that night recorded a Snapchat video together and sent it to one of those friends.

After returning to their respective colleges, Mr. McMillan messaged Ms. Hubbard on Facebook and they exchanged phone numbers. When each learned that the other had plans to be in New York City that May — Ms. Hubbard to begin a summer internship and Mr. McMillan for a training session ahead of a summer internship in San Francisco — they made plans to meet for a first date at the wine bar in Manhattan.

They managed to fit in one more date before Mr. McMillan had to leave for San Francisco. Although they hadn’t made concrete plans to keep in touch or see each other again, they soon found themselves connecting on FaceTime for hours each night.

“It was clear that there was something serious here,” Mr. McMillan said. In June 2016, a few weeks after their first date, he asked Ms. Hubbard to be his girlfriend over FaceTime.

The next month, she flew to San Francisco and they spent a romantic weekend in Sonoma, Calif., and the nearby Napa Valley. Later that summer, he joined Ms. Hubbard and her family, who live in Stamford, Conn., on a vacation to Martha’s Vineyard in Massachusetts.

In the fall of 2016, after he returned to Vanderbilt and she to Harvard for their final year of college, they began to regularly visit one another every few weeks. That November, Ms. Hubbard spent Thanksgiving with Mr. McMillan’s family in Clarkston, Ga.

After graduating from college, Ms. Hubbard moved to San Francisco and then to New York City, and Mr. McMillan to Atlanta and then to Austin, Texas. They continued to date long distance for years, maintaining their habit of visiting each other every few weeks, until March 2020, when the pandemic set in. Ms. Hubbard at the time was staying with Mr. McMillan in Austin, and never left. (The couple estimates that by then they had traveled about 500,000 miles over the course of their romance.)

Ms. Hubbard now works remotely as a senior product manager at Flex, a tech company in New York that has a namesake app for paying rent. Mr. McMillan works remotely as a senior associate at Growth Street Partners, an investment firm in San Francisco.

In August 2021, they became engaged while on vacation in Martha’s Vineyard, where Mr. McMillan proposed on the beach in front of both of their families.

“It was one of the happiest moments of my life,” Ms. Hubbard said. “It was really so splendid.”

The couple were married Aug. 13 at the Arlo, an events space in Austin. The Rev. Dexter Rowland, a family friend of Mr. McMillan and a pastor at the New Piney Grove Missionary Baptist Church in Decatur, Ga., officiated at the ceremony before 160 guests, who were required to provide negative Covid test results before attending.

“It’s just so clear to me that Caroline is a gift, she’s a blessing from God,” Mr. McMillan said about his wife, who is taking his last name. “I couldn’t imagine life without her.”

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