10 Romantic Films to Watch Every Autumn

Two of the things I love most in this world are the month of October and, well, love. When it comes to love and autumn, I would be hard-pressed to find a better way to indulge than by settling down for a few of my favorite lovey-dovey movies each year once the leaves begin to change. If you’re in dire need of some films to get you in the mood for pumpkins, cozy sweaters, scenic walks, and of course finding the love of your life, check out the ones on this list!

1. Love Story (1970)

dir. Arthur Hiller

Love Story is the classic tale of handsome, pretentious, rich guy falls for sassy, smart, working-class girl, with a tragic twist, of course. The film takes place during the Fall Semester at Harvard University where our two lovers, Jenny and Oliver, meet and fall in love. Love Story is recognized as the 9th most romantic film by the American Film Institute, and though I recall watching it as a young girl and thinking it was five hours long, it clocks in at just under an hour and forty minutes. If you’re looking for a classic to really bring out the nostalia of fall, this is your film.

Paramount Pictures

Paramount Pictures

2. When Harry Met Sally (1989)

dir. Rob Reiner

I won’t pretend that I’m unbiased when it comes to this film. It’s my second favorite of all time, and everyone should see it. Starring Meg Ryan and Billy Crystal, When Harry Met Sally is the epitome of what a rom-com is supposed to be. It has romance, it has comedy, and it feels whole and real. The film primarily toys with the question, “can men and women ever really be just friends?” Set in NYC during the fall and winter months, the film boasts some gorgeous scenery, and the soundtrack by Harry Connick Jr. is warming to the ear.   

Columbia Pictures

Columbia Pictures

3. You’ve Got Mail (1998)

dir. Nora Ephron

Nora Ephron, who wrote the screenplay for When Harry Met Sally, favored a number of ingredients for her films. She loved New York—specifically in the autumn—she loved strong female leads, and she loved for Meg Ryan to play those leads. You’ve Got Mail was made nearly a decade after When Harry Met Sally, but it still has many of those stylistic elements that Ephron is known for—witty banter, love interests that seem to detest each other, and nostalgia. Staring Tom Hanks and Meg Ryan, You’ve Got Mail is a cute tale about how love always seems to crop up where it’s least expected.

Warner Bros.

Warner Bros.

4. Runaway Bride (1999)

dir. Gary Marshall

This sweet 90s classic is definitely underrated, and if you’re looking for a feel-good comedy that’s certain to have a happy ending (no matter how many escapes-on-horseback it takes to get there), this is the one. The story follows a young woman (Julia Roberts) who has trouble following through on her numerous engagements, and the handsome reporter (Richard Gere) who winds up falling for her. The small town where the story takes place lends itself beautifully to a bit of fall scenery, and the chemistry between Gere and Roberts is always irresistble. 

Paramount Pictures

Paramount Pictures

5. Autumn in New York (2000)

dir. Joan Chen

I’ll clarify from the beginning that this film isn’t the best, but would a list of autumn romance films really be complete without it? I don’t think so. The film follows the relationship of a 40-something man (Richard Gere) and a 20-something woman (Winona Ryder) as they traipse around New York and around their own feelings. If you’re in the mood for a dramatic, tragic, winding tale of love where the actors don’t have great chemistry, give this a shot. At best, there are some lovely scenes of NYC in the fall.

Metro Goldwyn Mayer

Metro Goldwyn Mayer

6. The Lake House (2006)

dir. Alejandro Agresti

We all have those movies that we love because we saw them when we were young and impressionable, and when we watch them later in life, they may seem a little cheesy or exaggerated. The Lake House is a perfect example of one of those films (for me). The concept is muddled; two people live in the same house at different points in time, and they write letters to each other through the house’s mailbox while maintaining their existence within their own present. The result is a somewhat confusing, nostalgic, winding love story, but the mood of the film is perfect for a rainy fall afternoon. Plus, who can pass up Sandra Bullock and Keanu Reeves?

Warner Bros.

Warner Bros.

7. Juno (2007)

dir. Jason Reitman

While Juno takes place across several seasons, it has a pleasantly reflective autumn segment, and the coming-of-age themes of the film offer the perfect wistfulness for end-of-the-year viewing. If you aren’t familiar, Juno is a story of teen pregnancy, budding love, parental relationships, and adult romantic relationships, all tied together with a fantastic cast. The film made numerous top ten lists by critics the year it was released, and it won the Academy Award for Best Original Screenplay. If you haven’t seen it, you definitely should, and if you have, you definitely should again. 

Fox Searchlight

Fox Searchlight

8. (500) Days of Summer (2009)

dir. Marc Webb

Here’s a film that, despite the title, does not take place exclusively in summer. This quirky, not-a-love-story love story has all of the requirements for our list: nostalgic, romantic, set partially during autumn, etc. Staring Joseph Gordon-Levitt and Zooey Deschanel, the nonlinear narrative structure of the movie has drawn comparisons to classics the likes of Annie Hall and High Fidelity, and critics were quick to praise the film. The year it was released, I watched it at least once a week, and it makes a perfect annual fall film (though to be fair, you could watch it any time of year and it would seem appropriate).

Fox Searchlight

Fox Searchlight

9. Submarine (2010)

dir. Richard Ayoade

This is our only film on the list that does not take place in the United States. Considering that we so dramatically associate fall with American foliage and traditions, many of the films that feel so utterly autumn to us are American. This film though, is a lovely little breakaway from that. Submarine is set in Wales in the 80s. It’s a slightly eccentric and artistic coming of age film about an unpopular fifteen-year-old boy who has an infatuation with a girl in his class. The film is full of overcast skies, winter jackets, and wind-swept hair. I would place this as the most experimental movie on the list, but it genuinely has beautiful images and music.

The Weinstein Company

The Weinstein Company

10. Silver Linings Playbook (2012)

dir. David O. Russell

First, consider the cast: Jennifer Lawrence, Bradley Cooper, Robert De Niro, Julia Styles, and others. Following the story of a man with bipolar disorder as he tries to win back his ex wife and meets someone new along the way, the film has both intensely funny and seriously heartbreaking plot points. Jennifer Lawrence won an Academy Award for her role, and the general tension mixed with humor that the movie exudes is excellent. And we mustn’t forget that the film boasts some really nice fall features—leaves, football, sweaters (or garbage bags over sweaters), and so on. 

The Weinstein Company

The Weinstein Company

What are some of your favorite fall romances?

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