Sam & Austin In A Cinderella Story Didn't Actually Belong Together

The year was 2004: MySpace reached 1 million users, Friends aired its final episode, and the pop culture phenomena of A Cinderella Story starring Hillary Duff and Chad Michael Murray came to the big screen. Every girl who was also in the fourth grade like me swooned when the unlikely love story of Sam and Austin premiered, half because of the prince and princess trope we all grew up with, and half because of the One Tree Hill hottie. Now, 20 years later, folks are still fans of this duo (and even comparing them to Taylor Swift and Travis Kelce). But after a recent rewatch, now nearing my 30s, I know one thing to be true: Sam Montgomery and Austin Ames just aren’t meant to be.

Over the years, I remembered A Cinderella Story as a dreamy, adorable, and silly teen romance. On rewatch, I somehow even remembered all of Hilary Duff’s songs on the soundtrack by heart. But what my childhood memory lost of the movie (or perhaps I didn’t know because my frontal cortex wasn’t fully developed) was how silly, misplaced, and unromantic Sam and Austin’s relationship actually was.

First things first. Their relationship isn’t based on true love, but on the thrill of anonymity and a false reality. As Sam’s character often says in the film, sometimes pretending is better than reality, and that certainly matches her couple dynamic, too. The pair meet in an anonymous Princeton chat room, where they seemingly bond to the point of knowing everything about each other, via online chatting and old-school texting on flip phones. Austin even sends her beautiful poetry about how misunderstood he is and she shares how ambitious she is to go to her dream school, Princeton. At first, one might say Awwww to this meet-cute, but quickly, the ick set in as I realized that they don’t actually know anything real about each other.

They’re both giving unhealthy young love energy right from the get-go.

The two characters hadn’t been talking for that long: Sam’s best friend Connor revealed that her secret admirer had only been talking to her in cyberspace for one month. As a kid, I always remembered feeling like it was longer, and that their connection was so special. But based on their conversations and the pace of their status, they’re both giving unhealthy young love energy right from the get-go.

Plus, let’s not forget that when they meet IRL at 11 p.m. on the dot at their high school’s Halloween dance, Sam feels so nervous that she attempts to hide who she is by wearing a faux wedding dress and a white lace mask. Aside from the obvious — her outfit doesn’t hide who she is at all and Austin’s character is an idiot for not being able to tell she’s the so-called Diner Girl — their relationship begins with feelings of insecurity, doubt, and a lack of acceptance, and that’s never a good place to start.

Throughout the film, their social status doesn’t quite match up. That’s not always the case for a make-it-or-break-it relationship, but in this case, I think it is because they approach the world from polar opposite points of view. Austin hails from a wealthy family and is one of the most popular kids at school. In moments when his cool girlfriend Stacey and his other friends are making jokes at everyone else’s expense, he never stands up for what's right — even when they put Sam down for working at the diner or driving an old car. Sam, on the other hand, comes from less glamorous circumstances: her dad passed away when she was young, she’s working to save up for college, and she seems to be kind to everyone she meets. They aren’t exactly the picture-perfect match.

The sparks may seem like they’re flying but they might just start a terrible fire.

After the school dance, Austin posts “Where is Cinderella?” posters all over their school. But for fear of rejection, Sam doesn’t tell Austin who she is. Until a week later, when she’s outed by her stepsisters and the mean girls at school, who reveal her identity at the pep rally. Instead of going to each other right away, both of them ignore each other and don’t talk it out. As someone who writes about relationships, they’re only one week in and missing the most important key to a healthy partnership: communication.

Oh, and when they do decide to work it through, after Sam’s iconic line — “Waiting for you is like waiting for rain in this drought, useless and disappointing” — they still aren’t able to truly communicate with each other. They’re both drawn to each other’s idealized versions. She admires Austin’s charm but doesn’t fully grasp who he is. Meanwhile, Austin is mesmerized by Sam’s down-to-earth and “real” vibes, but he’s oblivious to her struggles. The sparks may seem like they’re flying but they might just start a terrible fire.

He only shows his vulnerability when he’s hiding behind a screen or while in costume.

Sam shows that she is That B*tch throughout the flick, from dealing with her horrible stepmother Fiona to getting into her dream school and finally being able to communicate who she is and what she wants out of life. But Austin doesn’t quite have that same level of maturity and drive. To me, he always seems unsure of himself, his priorities, and above all, how he is perceived. He says he doesn’t care about being popular, but does he show it? He says he’s a poet and wants something more than being an athlete, but does he claim that in front of others? Throughout, he only shows his vulnerability when he’s hiding behind a screen or while in costume.

In the end, when Austin rushes to kiss Sam underneath the rainfall after *very dramatically* leaving his football career behind, the two reunite. Except they don’t share real feelings, as much as make out. He briefly apologizes, and she seems pleasantly surprised. (Despite this, OG fans of the movie are still hung up on this scene. “Austin finally growing a pair for Sam in A Cinderella Story will always do it for me 😍🥹,” one X user wrote.)

As an almost-30-something, rewatching a ‘04 classic, I found myself asking what any woman might do after this crazy blast from the past: Will Austin rise to Sam’s level? Can Sam choose herself if the relationship doesn’t last? Are they going to end up happily ever after after riding off in Sam’s blue 1965 Ford Mustang convertible? In my very humble opinion, no.

On the bright side, Sam doesn’t seem completely oblivious to their young love: “As for me and Austin, we’re going to Princeton together, and got our happily ever after. Well, for now. After all, I’m only a freshman.”