Dennings starred in "Charlie Bartlett" in 2008, the story of a wealthy teenager (Anton Yelchin) who acts as a psychiatrist for his new public high school. She played Susan Gardner, Bartlett's love interest, and the daughter of the school's principal (Robert Downey, Jr.). Dennings appeared in "The House Bunny" that year, as Mona, a pierced feminist sorority girl. She also starred in the teen romance "Nick and Norah's Infinite Playlist", with Michael Cera. Dennings played Norah Silverberg, the daughter of a famous record producer, and was nominated for the International Press Academy's Satellite Award for Best Actress for the performance.