Top 10 Movies About Dating

Top 10 Movies About Dating By Kelly Seal.

I love movies, especially ones about relationships. Not because I’m some kind of sappy romantic at heart, but because I’m curious to see how other people date, break-up, or decide to commit to each other, even if they are only fictional characters. When it comes to love, I relate to characters who long for it, who fight for it, who mess things up, and who keep trying. I learn from their experiences and see what (and what not) to do.

In honor of these noble characters, I’ve put together a top 10 list of my favorite movies about dating and what they taught me. Feel free to add some of your own.

1. About a Boy.

About a Boy. I admit I’ve got a little crush on Hugh Grant, but that’s not the only reason to see this movie. His character taught me about the consequences of keeping yourself at a distance from people and not letting anyone in. He had a ton of girlfriends, but wasn’t happy. It was only when he started to show his own vulnerability that love came into his life.

2. Sleepless in Seattle.

Sleepless in Seattle. Obvious choice perhaps, but Tom Hanks and Meg Ryan taught me that when you want to find real love, you have to take big risks. She took a chance by traveling across country to meet him not knowing what to expect. Spoiler alert: it worked out for them.

3. 500 Days of Summer.

500 Days of Summer. This is not a happy view of relationships, but a real one. Joseph Gordon-Levitt plays a man who gets his heart broken when he falls madly in love with his girlfriend, only to find out that their relationship was not what he thought. This movie taught me about having perspective and seeing my partner for who he really is and not just who I imagine him to be, weaknesses and all.

4. Swingers.

Swingers. I live in L.A. so this has to make the top ten. Swingers taught me how we can be completely misguided by listening to bad advice about dating, even if it comes from well-meaning friends. Also, no phone stalking.

5. Bridget Jones’s Diary.

Bridget Jones’s Diary. I really identified with Bridget’s struggles of being single, her body image, and the heartbreak that comes with dating. This movie helped get me through some tough times, because I realized that we are never alone.

6. The 40 Year-Old Virgin.

The 40 Year-Old Virgin. How can you not fall in love with the naïve Steve Carrell, who is ashamed he’s reached 40 and still maintains his virginal status? He goes to great lengths to keep this embarrassing fact from his girlfriend, only to eventually discover she doesn’t care. This taught me that honesty is the best policy when it comes to relationships.

7. Amelie.

Amelie. If you can sit through subtitles, this gem of a movie is quirky, funny, and showed me that dreaming and a little creativity does work wonders in making love happen.

8. Garden State.

Garden State. This movie is an ode to singles who try to keep pain and heartache at a distance by refusing to feel anything at all. But when Zach Braff meets the vivacious Natalie Portman, he realizes that both pain and joy are worth living for.

9. When Harry Met Sally.

When Harry Met Sally. A classic tale of two friends who decide to cross the line and are left wondering how they really feel about each other. If you’ve ever thought about telling your BFF that you’re in love with him, watch this movie.

10. Sideways.

Sideways. We all make mistakes when it comes to love, and we all suffer heartbreak. But does this mean we should avoid rejection at all costs? Paul Giamatti’s character came to the realization that we must face our fears. Even small acts of courage in the face of rejection are the only way to find love again.

Which movies about love, do you love?
This article written by:  Kelly Seal, a freelance writer living in Los Angeles with her husband and two stepdaughters. She mostly writes about dating, since she spent many years searching through sketchy online profiles and hosting speed dating events. Her work has appeared in The Huffington Post, Slate, Examiner, MSN, Yahoo! Living, YourTango, and Cupid’s Pulse among others, and you can find her blog posts and videos on

  • Jez

    Yeah sideways is simply an awesome film.