The Mid Life Dating Files 2025

What movies or TV series have you watched more than 5 times?

Movies & TV Shows I’ve Watched More Than Five Times (…and What That Probably Says About Me)

Everyone has those comfort movies or TV shows they can watch over and over again. You know the ones—you can quote the lines, you know exactly what’s about to happen, and somehow you still laugh at the same parts every single time.

Apparently, I have…a lot of those. 😅

Let’s start with the reigning champion.

Christmas Vacation.

I’m not exaggerating when I say I’ve probably watched this movie over 100 times. Possibly more. At this point I don’t even need the TV on—I could probably perform the entire movie as a one-woman show if necessary. Every year when the Christmas season rolls around, it’s basically required viewing in my house. Clark Griswold’s dedication to holiday chaos is something I deeply respect.

Speaking of Christmas, there are a few others that have become annual traditions too:

Christmas with the Kranks Four Christmases The Holiday

Apparently, I enjoy watching other families survive awkward holiday situations almost as much as I enjoy my own. 🎄

Then there’s Pretty Woman, which I’m pretty sure half the world has watched multiple times. Let’s be honest—it’s basically a modern fairy tale. Girl meets rich guy, girl gets fabulous clothes, girl finds love, everyone lives happily ever after. Throw in some great one-liners and I’m hooked every time.

Now let’s talk TV series binges—because apparently when I commit to a show, I really commit.

Shows I’ve watched way more than five times:

Sex and the City (both the series and the movies) Game of Thrones Vikings Cougar Town Friends Seinfeld

Yes, that is a very strange mix of shows. I go from medieval battles and dragons straight to coffee shops in New York. My brain apparently enjoys both chaos and sarcasm.

Then there are the movies that just never stop being funny:

White Chicks Weekend at Bernie’s

I don’t care how many times I watch Weekend at Bernie’s—it still cracks me up. The entire concept is ridiculous, which is probably why it works.

And then there’s a category that surprises people:

All the Jaws movies.

Yes. Every single one. Multiple times.

I love sharks. Always have. And yes, before anyone asks—I have actually swum with sharks a few times. 🦈

And YES… cage diving with great white sharks is on my bucket list.

I know that might sound crazy to some people.

But I guess I might be a little crazy.

But… oh well. 😄

There’s just something fascinating about sharks. They’re powerful, mysterious, and honestly a lot more misunderstood than most people think. Watching the movies is fun… but seeing them in real life is even better.

Now we need to talk about the phase of life every parent understands:

When your kids are little, you don’t just watch their favorite shows…

You watch them 1,000 times.

I’m pretty sure I could still sing entire theme songs from memory thanks to:

Barney The Brave Little Toaster Bob the Builder SpongeBob Blue’s Clues

And basically every Disney movie ever made.

At some point during those years you realize something very important:

You’re not choosing the movie anymore.

The children are running the entertainment department.

Looking back, those were actually some of the sweetest memories… even if I did hear the same songs roughly 4,000 times.

So if someone asks me how many movies or shows I’ve watched more than five times, the real answer is:

Probably way more than I can count.

And honestly?

I wouldn’t change a single one of those rewatches. ❤️

Because sometimes the best movies aren’t the new ones.

They’re the ones that feel like home.