Brooke Boyarsky had been on “150 first dates,” many in the company of men who wouldn’t give her dreams a second thought.

“I can’t tell you the number of men I went on dates with, who, once they realized I went to Harvard Business School or I had a good job or I was career oriented, were like, ‘Well, uh, how soon would you consider leaving your career to raise a family,’” said Ms. Boyarsky, 33, the chief operating officer for production at Berkadia Commercial Mortgage, a Berkshire Hathaway and Jefferies Financial Group company in Chicago.

“These men that I dated would never say outright that they weren’t supportive of me,” she said. “Yet somehow they always managed to get their point across.”

Enter Alexander Pratt, a 31-year old M.B.A. candidate at the University of Chicago. Ms. Boyarsky met him in October 2013 through the dating app the League. (Mr. Pratt, who was previously a regulatory affairs manager at Endo Pharmaceuticals in Malvern, Pa., graduated cum laude with a bachelor of science in biochemistry from the University of Rochester.)

“Alex was different,” said Ms. Boyarsky, who graduated summa cum laude from the University of Pennsylvania and received an M.B.A. from Harvard.

“When I met Alex, he already had a great job and was on a great path, a superstar planning to attend some of the top business schools,” she said. “But yet very early on, he had said that what really matters to him was that I set all the career goals I had for myself.”

“He just took a genuine interest in helping me celebrate my successes,” she added. “His selflessness was just so far ahead of everyone else I had ever dated.”

Mr. Pratt and Ms. Boyarsky enjoyed their first date on Oct. 28, 2018, at a restaurant in Philadelphia.

“I soon came to realize that Brooke is very smart and very empathetic,” Mr. Pratt said. “There’s also the confident way she carries herself. And over time, when I kept hearing all of the great things her friends and colleagues say about her, that became very inspiring to me, and something I wanted to learn about and emulate.”

That first date went so well that Mr. Pratt didn’t mind that he had chosen to be with her instead of watching his beloved team — the Boston Red Sox — defeat the Los Angeles Dodgers in Game 5 to clinch the World Series.

For their second date a couple of weeks later, he spent a small fortune on tickets so that Ms. Boyarsky, who was raised in Dallas, could see the Cowboys play in Philadelphia on Nov. 11.

That morning, Ms. Boyarsky came down with a horrible stomach flu, and Mr. Pratt did not think twice about giving away the tickets and driving over to see her, chicken soup in tow, at her home in Philadelphia.

That evening as they talked, he mentioned to her that he had already started a 529 college savings plan in case he ever had children of his own.

“When I think of generosity and spirit, and the kind of person I’d want to raise a family with, I think of Alex,” Ms. Boyarsky said. “There is no one like him.”

The two were married Nov. 13, 2020 at the First Municipal District, Marriage and Civil Union Court of Chicago. Jackie Marie Portman-Brown, a Cook County Judicial Circuit judge, officiated.

After delaying their wedding because of the coronavirus, the bride and groom also decided to begin planning the reception, which will be held next November in Dallas.