Grossman was born and raised in Los Angeles, California. She attended Crossroads School for Arts & Sciences, where she directed plays. She started acting in her senior year at Sarah Lawrence College.
In 1999, Grossman was cast in her first major role, playing supporting character Mary Cherry in The WB high school drama series Popular. She had auditioned for the roles of Sam McPherson and Nicole Julian on Popular before having the part of Mary Cherry written for her.[citation needed] After Popular, Grossman joined the cast of The WB sitcom What I Like About You with Amanda Bynes and Jennie Garth. She had a recurring role in the first season before being added to the main cast in the second season. She played Lauren, the co-worker and best friend of Val Tyler (Garth).
On television, Grossman has appeared on Nip/Tuck, Charmed and CSI: Crime Scene Investigation, amongst other television series. In 2011 she guest starred on ABC Family's Melissa and Joey, and in 2012 she appeared on The New Normal and Ben and Kate. On film, Grossman appeared in Miss Congeniality 2: Armed and Fabulous in 2005. She appeared in two movies in 2006, Running with Scissors in an uncredited role and in Itty Bitty Titty Committee as Maude.

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