How I Met Your Mother actor Josh Radnor's second directorial offering sees Olsen play a college student who offers Radnor the chance to relive his glory days.
Digital Spy sat down with Olsen to discuss moving to lighter fare, working with Radnor and if she has any obsessions similar to a Liberal Arts character's connection to David Foster Wallace's Infinite Jest.
"I have a handful of movies that I have on my computer for travelling that I always watch to go to sleep - one's Tootsie, the others are Manhattan and Roman Holiday.
"Those three movies I'll watch over and over again.
"I guess from a young age Gone with the Wind became my most perfect movie in my mind.
"We had to write a hero's story in one of my academic classes when I was 11 and you learned about the perfect structure of a hero's story. I literally wrote about Clark Gable rescuing people during the Civil War and pretended it was an original idea!"
Liberal Arts opens in UK cinemas on October 5.