October 8th, 2012 by Simone Paget

Top 10 Movies About Dating

If I said I didn’t enjoy watching fictional characters fall in love on screen, I’d be lying. I love a good romantic comedy – especially if it’s a movie that shares little nuggets of wisdom about dating and love. Here are a few of my favourite movies about dating & what we can all learn from them:

1.  Singles:  This romantic comedy from the 90′s focuses on a group of singles living in Seattle. It’s about break-ups, makeups and all the little games we play when dating. Even though this movie is almost 20 years old, what it has to say about love and dating (ie. that you should just be yourself and be true to your feelings) is timeless.

2. You’ve Got Mail: Two business rivals hate each other in person but unknowingly fall for each other online. The lesson here: when it comes to dating, there’s usually more than meets the eye – both online and off – and sometimes people will pleasantly surprise us.

3. Reality Bites: This movie about a bunch of recent college graduates living and looking for love in Houston is another favourite from the 90′s that still rings true. When Winona Ryder dumps “Mr-Good-on-Paper” Ben Stiller for her  scruffy but oh-so-hot BFF Ethan Hawke, it reminds us that although life can be pretty confusing at times, you should always follow your heart.

4. 500 Days of Summer: This quirky romance is about Summer, a young woman who doesn’t believe in falling in love and Tom, the man who falls head over heels for her. What we can learn from it:  Dating involves a lot of trial and error. People aren’t going to always share your feelings. However, all the ups and downs are totally worth it once you meet the right person.

5. When Harry Met Sally: This movie about two best friends who fall in love tackles the classic dating conundrum: can men and women really just be friends and what happens when you cross that line? – a situation that I think most of us can relate to.

6. Sleepless in Seattle: This classic romantic comedy starring Meg Ryan and Tom Hanks has a clear message: when it comes to love, sometimes you have to take a giant leap of faith in order to find the real thing.

7. Before Sunrise: A ridiculously good looking pair  (Ethan Hawke and Julie Delphy) meet on a train in Europe and end up having spending one perfectly romantic night together hanging out in Vienna. What we can take away from this one: Not all dating experiences are going to lead to long term relationships however that doesn’t mean they can’t be worthwhile and enjoyable.

8. Pretty in Pink: When Andy – a working class girl from “the wrong side of the tracks” falls in love with Blane – a sensitive rich guy they encounter resistance from their respective social circles. However, in the end love prevails – proving that even if your backgrounds are different, you can still fall in love and make it work.

9. Love Jones:  When Darius (Lorenz Tate) and Nina (Nia Long) meet  it’s love at first sight. However, the pair then embark on a love affair that is full of complications. The undeniable chemistry between Darius and Nina has you rooting for them until the very end of this realistic film about the ups and downs of dating.

10. Garden State:  Andrew (Zach Braff) has felt numb for years however when he meets and falls for Sam (Natalie Portman) he’s awakened to the possibility that there’s more to life and love. The lesson here: Don’t just sit around waiting for life (and dating) to happen. Open your eyes to new possibilities & take action! You may just find someone who is perfect for you.


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Simone is a freelance writer and author of the sexy and irreverent blog Skinny Dip. When she’s not writing her heart out about everything to do with love, sex and relationships, she loves wandering her city with a large cup of coffee in hand, in search of the next great story. You can visit her blog, follow her on twitter or catch up with her on Facebook. Skinny Dip

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