Samantha Montgomery is the Cinderella character of the film. She was portrayed by Hannah Robinson as a 10-year-old and Hilary Duff as a 18-year old teenager. She is a tomboy and lived a great life as a child until her father Hal Montgomery foolishly married Fiona. But all went well for Sam until the Northridge Earthquake strikes and Hal is killed. All the belongings of Hal went to Fiona. Since then, Sam had been mistreated by her jealous stepfamily. Despite their cruelty, Sam finds comfort through the diner staff consisting of Rhonda, Eleanor and Bobby and through her best friend, Carter.
Eight years later, Sam was employed at the diner which used to be Hal's Diner but was now Fiona's. But Sam had a secret IM pen pal whom she chats with everyday. She was unaware that it was Austin Ames until the Halloween Homecoming Dance. After the encouragement of her friends she goes to the dance as Cinderella and meets Austin as Prince Charming. They get to know each other and share a romantic dance. Before he can unmask Sam, the alarm on her cellphone goes off and she leaves. Austin and Sam are named Homecoming Prince and Princess but Sam leaves the dance in order to get back at the diner before midnight and she drops her cellphone while rushing out.
When Sam's stepsisters Brianna and Gabriella found out that Sam was Austin's Cinderella, they along with Shelby Cummings become jealous and told everyone at the school pep rally by performing a skit as well as naming her and imposter, and Sam leaves feeling angry and humiliated with only Carter to help her out. Later that day, Fiona gives Sam a fake rejection letter from Princeton, even though she was actually accepted, in order to make Sam stay and still serve her. Fed up with Fiona's abusive bossiness, Sam says "No" for the first time, quits her job and moved out to live with Rhonda. At the big Homecoming Game, Austin left the game and chased after Sam before she could leave. To Shelby Cummings and the stepsisters' dismay, Sam and Austin kissed in the rain as the Fighting Frogs win the game. Sam narrates that she and Austin got sick from being in the rain, but she hasn't been seen being sick.
Later Sam, after recovering from her cold, finds Hal's will and now owns everything! She restores Hal's diner to its former glory and goes off to Princeton with Austin in the end after her gives back her cellphone.
Sam is a very sweet girl even to her stepfamily. But as a teenager, after being publicly humiliated at school, Sam finally gets tough on her stepsisters and Fiona. She tells Fiona that she can mess with anything she wants: Fiona's hair, nose, face, and even Hal's Diner, but Fiona is done messing with Sam herself, the wrong thing Fiona chose to mess with. Sam can be unconfident especially around Austin until he chased after her before she left the game. She is very geeky but very beautiful. She takes extra AP classes to graduate a year early to escape Fiona, and she is a straight-A student.
Sam is a tomboy. She is very beautiful, both inside and out. She is very strong inside.
- Sam (everyone)
- Diner Girl (Shelby Cummings)
- Sammy (Fiona & Eleanor)
- PrincetonGirl (Austin Ames)
Terry is the only character to call Sam "Samantha".
Sam has blonde hair. She is seen wearing different outfits mostly boy clothes, and her signature color is blue.
As a ChildEdit
As a child, Sam wore a light blue dress in the beginning of the movie. While playing softball with Hal, she is seen wearing a boy red and blue top. During Hal and Fiona's wedding, she has her hair in pigtails and is seen in a blue dress. During the earthquake scene, she is wearing a blue top and blue pajama bottoms.
As a TeenagerEdit
Sam is seen wearing mostly jeans and shirts and does not dress very girly. Her work uniform included roller-skates, a black T-shirt, blue jeans, and a peach apron. She usually has her hair in a ponytail during work. At the Halloween Homecoming Dance, Rhonda gave her a beautiful dress and a white mask. The dress is a wedding dress that Rhonda had been saving. It is strapless and has lace, beads, and the skirt is poufy.
Sam has lots of likes and dislikes. We all know her biggest dislikes: her stepfamily.
- Hanging at Hal's
- Austin Ames
- Her snowglobe (until it was broken during the Northridge Earthquake)
- The color blue
- Carter Farrell
- Shelby Cummings (and Madison and Caitlyn)
- Public humliation
- Being teased
- Fashion (except Rhonda's dress)
- Her stepfamily's mockery
- Being treated like Cinderella (possibly)
- Losing her cellphone
At the beginning of the movie, Sam is seen to be very close to her father and referring to him as her "best friend". It is unknown what happened to her mother . When Hal married Fiona, Sam tries to be nice to them but Fiona, Gabrielle and Brianna all treat her poorly while Hal appears to be oblivious to the situation.