2008 schloss Lilly einen Modelvertrag mit Davidoff Cool Water ab. 2014 veröffentlichte Lilly ihr erstes Kinderbuch The Squickerwonkers, das bisher auf Englisch, Portugiesisch und Deutsch erschien.
Im Juni 2011 gab Peter Jackson bekannt, dass Lilly die Rolle der Tauriel in der Verfilmung von J. Lilly war von 20 mit dem kanadischen Eishockeyspieler Murray Hone verheiratet.
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Then, on CSI: NY as Sarah Endecott, in the 2005 episode "Manhattan Manhunt".
Dennings made her feature film debut in Hilary Duff's Raise Your Voice in 2004 as Sloane, a somber piano student.
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.
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.).
She was cast for a five-episode run on The WB's Everwood, but the role was recast with Nora Zehetner.
Dennings continued working on television, guest-starring on Without a Trace as a teen whose boyfriend goes missing, and on Less than Perfect in 2003.
In September 2008, Dennings hoped to make Don De Lillo's novel End Zone into a film.
Actors Sam Rockwell and Josh Hartnett were involved, but the project was not greenlit because of its controversial subject matter of nuclear war.
Since 2011, she has starred alongside Beth Behrs in the CBS sitcom 2 Broke Girls.