The story about Cinderella was adapted into a movie more than once. But, every version has its own flavour and is different in its own way. This time, the Cinderella is Samantha Montgomery (Hilary Duff), a blonde gorgeous teenager who lost her dad when she was only 8 years old. From that point of, she's been living with her stepmom Fiona (Jennifer Coolidge) and two of her stepsisters Gabriella and Brianna (Madeline Zima and Andrea Avery). Their world included popular kids like Austin Ames (Chad Michael Murray), Shleby Cummings (Julie Gonzalo), and the rest of the crew. Besides the high school friend Carter (Dan Byrd) her only other friend was her pen-friend from an online chat, a person called Nomad. They shared their wishes and thoughts and were really connected, but through emails and sms texts. After he finally asked her to go with him on a Halloween costume party as a date, she was thrilled. As she arrived to the agreed place, she found out that her pen friend is actually Austin. As she was masked as Cinderella, after she ran off in the middle of the night, Austin had no idea who she is and started looking for her all over the school. As he somehow manages to track her down, he finds out that she is a girl that works in a Diner, which is pretty humiliating for him. After all the fuss, Sam comes across her dad's will and finds out a lot more than she had expected. Will this prince Charming be a gentleman or a spoiled brat?