Here’s Why ‘Serendipity’ Is Problematic As Hell–And Why We Still Love It

Everyone’s favorite leave-it-up-to-fate movie, Serendipity, came out 20 years ago. Starring John Cusack and Kate Beckinsale, two people meet in a busy department store during Christmas and hit it off. They spend the evening eating ice cream and ice-skating around Manhattan, but there’s a problem: They’re both already taken. Beckinsale’s Sara insists that they leave their potential love to fate, and it takes years to get there. While it’s been a fan-favorite since its release in 2001, I think we can all agree that Serendipity is problematic as hell. Here’s why.

They are never not cheating on their partners.

Sara and Jonathan meet. / Serendipity (2001)

I’m going to start with the big one. This movie is filled almost entirely with cheating. When Jonathan and Sara first meet, they’re already coupled up. Even so, they spend the whole night together in an extended romantic date. Years later, they’re both engaged to other people yet still go on epic adventures to find each other.

It’s damn near impossible to support these people when they spend the whole movie cheating on their significant other. While they aren’t actually sleeping around, the amount of emotional adultery is staggering. Imagine you were their fiancés. It’d be devastating to find out that they’d been spending this much time and energy seeking someone who wasn’t you. Big yikes.

Lars may have sucked, but Halley was a sweetheart.

In the present day section of the movie, years after Sara and Jonathan’s original meeting, we’re introduced to their current future spouses. Sara’s fiancé Lars, played by John Corbett, is a new age musician. It’s clear from the outset that we’re supposed to dislike him. He’s annoying and weird, his music sucks, and he never listens to Sara. Okay, clearly they did this to make us feel okay with Sara cheating on him.

But Halley, Jonathan’s fiancée? She’s nothing be a sweetheart. She’s understanding with him when he starts to act shady. Honestly, she seems like a nice girl, which makes this so much worse. Don’t hurt Halley, dammit!

There is some serious stalking going on.

Jonathan and Dean mid-stalk. / Serendipity (2001)

Why do movies always try to make stalking look romantic? Serendipity isn’t the first one to do this, but it’s such a huge part of the plot. While Sara tries to use fate to find Jonathan, Jonathan tries to find Sara through shady stalkerish means. He spends hundreds of dollars at the department store to learn her name. He find her old roommate to learn more about her. He and his friend even trick people into endangering their jobs just for a little crumb of info. I understand the sentiment, but wow, dude. Stalking’s not cool.

I say this, but I also look people up on social media as soon as I meet them, so maybe I’m not one to talk. Perhaps if Facebook existed when this movie was made, things would have gone a little differently.

Let’s all collectively agree that we’re done with cheating plots.

I know I’m bringing up the cheating thing again, but seriously. Cheating is not romantic. It’s no way to start a relationship. Someone should start a petition for Hollywood to stop making this a rom-com plot, ASAP.


But… It’s still great, and here’s why.

Okay, hear me out: The movie still slaps. Problematic as it is, it still has some solid redeeming qualities.

We could all use best friends like Molly Shannon and Jeremy Piven.

As problematic as the main couple is, their saving grace is their taste in friends. Molly Shannon’s Eve and Jeremy Piven’s Dean often provide the voice of reason why things are going off-course. This is especially the case for Dean, who gives Jonathan a wakeup call in the form of some tough love. Because if Jonathan is doing this much to find Sara, should he really be marrying Halley. Speaking of which…

They finally broke up with their significant others in the end.

Okay, NOW you can be together. / Serendipity (2001)

Without that ending, them getting together wouldn’t have been acceptable. This is really the key to why Serendipity is still a good movie. Both Jonathan and Sara finally gave up on finding each other, yet still broke up with their fiancés. They realized that if they aren’t fully happy with the ones they’re with, being with them is a big “hell no.” It’s better to be alone. It’s only then that they find each other and get together, no longer using the cheating plot. Hell fucking yeah.

It’s just good. What can I say?

Sure, we can pick apart movies. I just did, after all. But in the end you have to ask yourself: Does this movie make me feel good? If yes, who cares about all the other details. And Serendipity makes so many of us feel great.

If you’re feeling nostalgic, you can watch Serendipity right now on Netflix, Hulu, and Paramount Plus.