Flanagan, who is from North Barrington, Illinois, rose to prominence as a contestant on season 24 of The Bachelor in 2020. During her appearance on the ABC reality series, she vied for Peter Weber’s heart. Weber ultimately ended the season trying to make things work with contender Madison Prewett, whom he split with days later.
Before being cast on The Bachelor, Flanagan attended the University of Alabama and graduated with the class of 2014. As an undergraduate student, she was a member of the Zeta Tau Alpha sorority, served as a Campus Liaison for Serengetee and was a Global Ambassador for the Semester at Sea program. She was also a President’s list and Dean’s list recipient.
Flanagan then attended law school from 2014 to 2017 at Chicago-Kent College of Law at Illinois Institute of Technology. After completing her studies and earning her J.D., she landed a position as an attorney within her father’s law firm, Flanagan Bilton LLC, in Chicago.
Flanagan was eliminated from The Bachelor in week seven. However, she reconnected with Weber amid the coronavirus quarantine in March 2020.