Finding Her ‘Barack Obama’ With the Help of a Friend

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Olivia Castor and Austin McNair met at Harvard through Ms. Castor’s roommate, who had a knack for matchmaking.

By Anna Grace Lee

One day in April 2017, during the spring semester of her senior year at Harvard, Olivia Melissa Castor received a call from her roommate, who said, “Liv, I found your Barack Obama.”

Ms. Castor said she wasn’t interested, but it was too late. The roommate was already on her way to their dorm room, accompanied by her boyfriend and the mystery man. So Ms. Castor quickly changed into a cute outfit, and she soon met Austin Leroy McNair.

They chatted briefly and exchanged numbers, but neither of them reached out to the other: Mr. McNair had only recently moved to Boston after graduating college, so he was focused on work, and Ms. Castor was about to graduate.

But seven months later, after Ms. Castor had finished school and started working, she thought of Mr. McNair. She texted him out of the blue, unsure if he would remember her.

“I knew exactly who she was,” Mr. McNair said. Unbeknownst to her, he had been thinking about her since they met and had even looked her up online to see what she was doing after graduation.

They chatted and he invited her to a step show with his friends. After the show, she asked to stop by his apartment to use the bathroom — and to check out his place. That night, they ended up talking at his kitchen table for more than three hours.

Their first real date took place about a week later, when they met over drinks. She knew he was special that night when he walked her to her Uber ride and opened the car door for her. “I immediately texted my best friend,” Ms. Castor, 28, said.

“Olivia’s smile was radiant,” Mr. McNair, 29, recalled. Together, they felt a familiar ease, as if they had known each other for their entire lives.

They became a couple in February 2018. That September, they took a trip to New Orleans together — the first in a long list of destinations they would go on to visit around the world. Shortly thereafter, Mr. McNair left for India on a work assignment for about three months, and Ms. Castor flew there to visit him in November.

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In August 2020, Mr. McNair moved to Evanston, Ill., to attend business school at Northwestern University, while Ms. Castor went to Harvard Law School. They continued their relationship long distance, and by that fall, Mr. McNair knew he wanted Ms. Castor to be his “forever.” He talked to her best friend and her three sisters to plan an elaborate, multipart surprise proposal near where they had first met.

In September 2021, he told Ms. Castor that they were going to a promotional dinner event in Cambridge, Mass., where there would be photographers, so they had to dress up. When they arrived at the restaurant, he said that he had mixed up the time and that they were early. He suggested they go on a walk to while they waited.

When they walked by Ms. Castor’s old dorm, she pointed it out and said jokingly that they could marry in the courtyard there. “And I’m like, ‘Oh, interesting,’” Mr. McNair recalled. They reached a bridge, where he showed her a YouTube video he had made about their love story. At the end of the video, he knelt down.

When she said yes, their families came running and cheering from across the street. “It was an epic surprise,” Ms. Castor said.

Ms. Castor, who grew up in Rockland County, N.Y., has a bachelor’s in social studies and African American studies and a law degree, both from Harvard. She is a corporate associate at the law firm Kirkland & Ellis in Chicago. Mr. McNair, who grew up just outside Cleveland, has a bachelor’s degree in chemical and biomolecular engineering from Georgia Institute of Technology and a master’s in business administration from Northwestern. He is a director at the Chicago office of EY-Parthenon, a management consulting firm. In June 2023, the couple moved to Chicago.

They were married on Aug. 18 at the First United Methodist Church at the Chicago Temple by the Rev. Myron McCoy. They jumped over a broom, which was handmade in Haiti, where Ms. Castor’s parents are from. The bride wore her paternal grandmother’s pearls and a veil made by her maternal grandmother, and she had the buttons from her mother’s wedding dress sewn onto her own gown.

Afterward, they had a carnival-themed reception at Rockwell on the River, an event space, that included games, a magician, a stilt walker and a performer who poured wine while riding a bicycle.

The couple also took the opportunity to do some matchmaking of their own. To encourage new friendships, they paired up all of their 206 guests and decorated an area with a display of photo pairs, where guests searched for their matches.

For their first dance, the couple did a choreographed routine to “Conversations in the Dark” by John Legend that featured dips, spins and lifts, drawing cheers from the crowd.

Anna Grace Lee is a reporting fellow on the Styles desk at The Times. More about Anna Grace Lee