30 Days of Fall Movies: Week 1 Recap +Cozy Watchlist Picks
Every year, fall just seems to come and go. It’s my favorite season, but it always files by before I’ve had a chance to truly enjoy it. This year, I decided to challenge myself to slow down and soak in -one cozy movie at a time.
For the entire month of October, I’m watching a different movie every day that gives me all the fall feels-warm lighting, New York settings, cozy sweaters, and a little romance sprinkled in. I started, of course by asking ChatGPT for recommendations. After some refining, I ended up with a mix of comforting classics, heartfelt stories and cozy favorites.
Being completely honest, I started strong on day one -then immediately fell behind and questioned why I started this challenge! But I was able to catch up by day 7 to all the movies I had been missing and ended up loving the process. Here’s how Week 1 of my 31 day Fall movie challenge went.
Day 1: When Harry Met Sally
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Image sourced from Imdb
This movie has been on my list forever, Mostly because every bookish person I follow seems to love it. It follows Harry and Sally, tow recent grads driving to New York City who debate whether men and women can really be just friends.
The movies spans years and captures the evolution of their friendship with sweet interview clips of real-life couples in between- Which ended up being my favorite part. It’s cozy, witty, and romantic in a subtle way. Plus the fall scenes in New York ? Iconic. I called my mom after watching because she used to love Meg Ryan movies when I was growing up- it felt like a full circle moment.
Day 2: You’ve Got Mail
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Image sourced from Imdb
Another Meg Ryan classic! This one follows two pen pals who fall for each other online, not realizing they’re actually business rivals.
The set up instantly pulled me in- the AOL “You’ve Got Mail” nostalgia and cozy apartment vibes felt perfectly fall. Kathleens children’s bookstore assed to the charm, though I felt the story dragged toward the end. Still, it’s the kind of film that makes you want to curl up with hot chocolate and a good book.
Day 3: Dead Poets Society
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Image sourced from Imdb
This AMAZING coming of age story follows a group of boys at a 1950s boarding school whose lives are changed by their passionate English teacher. It’s emotional, thought-provoking, and unforgettable.
This movie hit me hard- it reminded me of the teachers who helped me think freely and see the world differently. It’s heartbreaking yet inspiring, and easily one of the most powerful films I’ve ever seen. I probably won’t rewatch it soon because of how heavy it is, but I’ll never forget it.
Day 4: Runaway Bride
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Image sourced from Imdb
After the emotional rollercoaster of Dead Poets Society I needed something light. Enter Runaway Bride.
Julia Roberts plays Maggie, a woman notorious for leaving fiancee at the alter. A journalist who writes about her tried to redeem himself by following her journey before her next wedding.
It’s fun, sweet and surprisingly reflective. Beneath the humor, its really about discovering who you are outside of other peoples expectations-something many of us can relate to.
Day 5: Julie & Julia
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Image sourced from Imdb
This one I initially did not have on my list when I first started. I had Fantastic Mr. Fox in this spot. I truly did give it a shot. I remember being young and trying to watch this movie and I never could finish it. I thought I would be able to get through and watch it but each time I tried to watch it I fell asleep. I ended up trying to find a replacement and when I did I got Julie and Julia.
Julie & Julia follows Julie Powell as she cooks her way through Julia Child’s cookbook. I didn’t realize it was based on a true story until after watching, but it made me fall in love with both women determination and creativity. It’s such a cozy, inspiring watch perfect for fall.
Day 6: Good Will Hunting
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Image sourced from Imdb
Another emotional one. Will is a genius working as a janitor at MIT who solves a complex math problem that even professors can’t figure out.
This movie explores identity, trauma and the pressure to live up to potential. I loved how it shows that where you come from doesn’t define where you can go. It’s introspective, emotional and so well written.
Day 7: The Craft
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Image sourced from Imdb
This 90’s teen cult classic follows four outcast girls who discover witchcraft and face the consequences of their power.
The moody cinematography, close ups and 90’s vibe had me hooked immediately. It gave me the strongest fall energy out of all the movies this week- dark, mysterious and fun. Easily one of my new seasonal favorites.
Final Thoughts
This first week was a mix of emotional highs and cozy comfort. I’ve already found new favorites and rediscovered classics I’ll rewatch every fall.
My Week 1 Favorites:
💔 Dead Poets Society- The Most Moving and Meaningful
🍲 Julie & Julia- Most Comforting
🧹 The Craft - The Most Fall Vibes Filled
I can’t wait to dive into Week 2! If you’re following along, comment below with your own cozy picks!