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.