Valentine's Day Films

Whether you're in love, looking for love or mending a broken heart, there's a Valentine's Day film for everyone. Here's my top film picks broken down into three categories…

20 films for those in a relationship or happily single and actively looking for love:

Clueless (1995) – A modern day retelling of Jane Austen's novel Emma, this film has stood the test of time to be one of the most quotable teenage romantic comedies.

Jerry Maguire (1996) – One especially for single mums. With lines like “You complete me” it's a romantic film but its sport management story also has substance.

Pride and Prejudice, the BBC production (1995) – Don't bother with that pathetic excuse for a film starring Keira Knightley as Elizabeth Bennet. Pass Valentine's Day evening watching Colin Firth as Mr Darcy and you won't be sorry.

Pretty Woman (1990) – Even hookers deserve to find true love. It's the film that made the world fall in love with Julia Roberts leading her to make other great romantic comedies like My Best Friend's Wedding, Notting Hill and The Mexican.

Grease (1978) – A musical love story about a summer love story. What's not to love? You can enjoy the romance and sing along.

Dirty Dancing (1987) – A young woman on a family vacation falls in love with a bad boy dancer. Every woman falls in love with Patrick Swayze after watching this film. “Nobody puts baby in a corner.”

My Father The Hero (1994) – A film about the extent a father will go to help his teenager daughter get her man, even if it means pretending to be her lover. Hilarious film with a great performance from Gerard Depardieu and a young Katherine Heigl.

It Happened One Night (1934) – A spoiled heiress runs away from her family and is helped by a man who is actually a reporter looking for a story. As classic as a film could be. Clark Gable at his finest.

Pretty In Pink (1986) – With hits like Sixteen Candles and The Breakfast Club, the 80's wouldn't have been the same without John Hughes. Pretty In Pink is one of his best works.

27 Dresses (2008) – Always the bridesmaid, never the bride. My favourite quote from the film: “I feel like I just found out my favourite love song was written about a sandwich.” The Benny and the Jets scene is so much fun.

10 Things I hate About You (1999) – The film that made Heath Ledger and Julia Stiles famous. A reworking of Shakespeare's Taming of the Shrew.

Suddenly 30 (2004) – On her birthday, a 13 year old girl wishes she was 30 and the next day wakes up trapped inside her 30 year old self. There's something likeable about how daggy Jennifer Garner is in this film. You can also dance along to Michael Jackson's Thriller in one particularly memorable scene.

Love Actually (2003) – A great British comedy that follows the lives of eight couples around Christmas time. Much better than similar films like Valentine's Day, New Year's Eve and He's Just Not That Into You.

The Princess Bride (1987) – My favourite film of all time. It has everything – true love, adventure and comedy. It makes me happy every time I see it.

When Harry Met Sally (1989) – Far superior than any other “complex friendship” film like Friends With Benefits or No Strings Attached. The chemistry between Billy Crystal and Meg Ryan is fantastic.

Sleepless In Seattle (1993) – A recently widowed man's son tries to find him a new love. Romantic and sweet. Another classic.

Bridget Jones's Diary (2001) – Renee Zelwegger plays a woman aged in her 30's who is single, chubby, mildly alcoholic and smokes too many cigarettes. She also look for love in all the wrong places. Colin Firth and Hugh Grant are so good in this film.

Girl Happy (1965) – A mobster hires a singer to keep an eye on his daughter during spring break. My favourite Elvis Presley film. So much fun and you can sing along with the songs too.

My Big Fat Greek Wedding (2002) – A Greek woman falls in love with a non-Greek and must convince her family to accept him. My family reminds me a little too much of the family in this film. This is especially one for anyone with a European background.

His Girl Friday (1940) – A newspaper editor tries to stop his ex-wife from remarrying. Cary Grant at his very best. Charming, funny and entertaining.

10 films for those who like to have a good cry on Valentine's Day:

Gone With The Wind (1939) – This classic novel-turned-film is set in America's south during the civil war. Not even manipulative Scarlett O'Hara gets her man in the end but, “Frankly my dear, I don't give a damn.”

Casablanca (1942) – One of the most quotable films ever made, Humphrey Bogart is heroic, broody and cool. “We'll always have Paris.”

Dr Zhivago (1965) – Classic novel. Classic film. It tells the story of a Russian doctor who is married but falls in love with another woman during the Bolshevik revolution.

The Notebook (2004) – Based on the popular novel by Nicholas Sparks, every woman will cry and every man will wonder why. This is why men don't understand women.

A Walk To Remember (2002) – I cried when I read the book and I cried when I saw the film. Such a moving story. Such a moving story about teenage love and illness. Great performances by a young Mandy Moore and Shane West.

Titanic (1997) – Most women will probably rank this film in their top 10. The film catapulted Leonardo DiCaprio and Kate Winslet to stardom. Such a beautiful film by James Cameron.

Romeo + Juliet (1996) – Leo sure does know how to make us cry. Claire Danes is great in this film too. Director Baz Luhrman has done an amazing job with making this modern retelling of a Shakespeare tragedy entertaining for a new generation.

Ghost (1990) – After being killed during a botched mugging, a man connects with his partner as a ghost. The concept is kind of ridiculous and yet, everyone loves this film. You know why? Because Patrick Swayze, Demi Moore and Whoopi Goldberg are fantastic in it.

Splendour In The Grass (1961) – A young girl's forbidden and unrequited love for a rich boy drives her to madness. Natalie Wood gives one of the best performances of her career in this film. It's heartbreaking to watch.

P.S. I Love You (2007) – A recently widowed woman learns that her husband has left her a series of letters to help her move on. One of the rare times I will say the film was better than the book. I cried and cried and cried.

5 films for those miserably single and hating Valentine's Day:

Closer (2004) – This play-turned-film gets quite ugly as a stripper (Natalie Portman), a writer (Jude Law), a photographer (Julia Roberts) and a dermatologist (Clive Owen) have messy romantic entanglements.

Revolutionary Road (2008) – Leonardo DiCaprio and Kate Winslet re-team to tell the story of a marriage falling apart in the 1950's. This film is so depressing, you really have to be in the right mood to watch it.

Who's Afraid of Virginia Woolf? (1966) – Mike Nichols made his directorial debut with this play-turned-movie starring real-life couple Elizabeth Taylor (who won an Oscar) and Richard Burton. When the unhappy couple invite a younger couple over for a nightcap, things seem to fall apart even more for them. There's a lot of witty dialogue in this film.

Match Point (2005) – Woody Allen is a great film-maker and he's given audiences an interesting anti-morality tale in Match Point. A social-climbing ex-tennis pro (Jonathan Rhys-Meyers) marries into money but has a passionate fling with an aspiring actress (Scarlett Johansson) who causes more trouble than she's worth.

American Beauty (1999) – Stage director Sam Mendes made quite an amazing film debut with this comic drama about a dysfunctional family. Kevin Spacey plays a husband and father going through a mid-life crisis who begins lusting for his daughter's friend. It won the Oscar for best actor, best director and best picture.

What are your favourite films to watch on Valentine's Day?


  1. Angie what a great list. Some of my very favorites in there. Must have taken you ages to compile. My 11 year old son recently watched Titanic for the first time (yes, I have trained him well) & loved it. But I don't think it was the romance for him. I think it was the sinking ship. A good film when there is something for the boys as well. And The Notebook-my hubby & I pulled over in the car after the preview and sobbed like idiots for 5 minutes. Thanks for taking the time to make such a substantial list.

  2. "Pretty Woman (1990) – Even hookers deserve to find true love." Hahaha you crack me up! Great list :)

  3. Very comprehensive post, I think you've catered for all tastes, well done.
    Grease has been a favourite of mine ever since I watched it at the cinema as a child and I like Sleepless In Seattle too, I'd have given up everything in a heartbeat for the 1993 vintage Meg Ryan!
    My favourite of all the films you mention though is When Harry Met Sally. Such a great film, it grows in stature with every year that passes.
    Enjoy your Valentine's Day.

  4. When Harry Met Sally and Grease are major favourites of mine too, Paul.

    Well Jules, it's true! Hookers deserve love! Haha.

    I'm so glad he liked Titanic, Susan. I think males can appreciate it. I cry every time I watch and read The Notebook.

  5. Great list! I think my top 5 are... Dirty Dancing, Titanic, The Notebook, 10 Things I Hate About You and My Father The Hero. But it's a really tough choice.


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