The movie is about a young woman named Shelly Darlingson (Anna Faris) who finds herself in a pickle. She is clueless about how the real world works and has no real interests beyond the latest celebrity gossip. She has also spent the last few years living in the Playboy Mansion. She has not wanted or needed anything, and has lived the life of luxury. The day after she turns 27, she finds herself being asked by Hugh Hefner to pack up and leave. Shaken, she finds her world turned upside down. She eventually winds up at a sorority house where she is taken by the women who live there. The young women are more clueless about life than she herself is. She meets a young man named Oliver (Colin Hanks) who is at first put off by her clueless nature and is the first guy to reject Shelly. Shelly and her new friends shake it off and go back to doing what they do best-makeup, clothes, celebrity gossip and keeping up with the latest trends. Shelly gets the biggest reality check of her life when she allowed to return to the Playboy Mansion and realizes the life she was living isn’t the life she wants.