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

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.