The Most Romantic Grand Gestures in the Movies ...

1. The Five-Year Engagement

Jason Segel’s entire plan to arrange his and Emily Blunt’s shotgun wedding was a grand gesture because it took all of the pressure off his fiancé and allowed to enjoy her day.

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2. Bridget Jones’ Diary

When Bridget thought she had lost her chance of love forever, she never expected that all Colin Firth had done was pop to the store to buy her a brand new diary!

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3. Never Been Kissed

Drew Barrymore’s apology to Michael Vartan for lying about her identity involves two grand gestures: an announcement in the local paper and a kiss on the baseball field!

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4. Sixteen Candles

Everybody forgets Molly Ringwald’s birthday, that is, of course, everyone except her dream crush who proceeds to surprise her!

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5. Pitch Perfect

Anna Kendrick’s had never seen The Breakfast Club until her love interest showed her, and she made the most of the moment at the end to recreate the film’s climax in a big way.

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6. 10 Years

The reveal in 10 Years that Oscar Isaac’s famous high school song is actually about Kate Mara is one of the sweetest gestures in recent movies!

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7. Pretty Woman

She wanted the fairytale and she got it when Richard Gere conquered his fear of heights to climb the fire escape. Let’s not forget he held a red rose in his teeth.

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8. Confessions of a Shopaholic

Hugh Dancy’s gesture of anonymously buying Isla Fisher’s beloved scarf so that she could keep one item from her past is super sweet.

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9. From Nada to Prada

This movie contains a wonderful gesture between two neighbors who don’t initially get along but come through for each other in the end.

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10. (500) Days of Summer

It’s a small gesture but big for the couple in the movie, when they let go of their inhibitions and shout obscenities together in the park!

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11. P.S. I Love You

The love letters that Gerard Butler leaves for Hilary Swank to discover after his death are so incredibly heart-warming and emotional.

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12. Silver Linings Playbook

Bradley Cooper and Jennifer Lawrence trade gestures in this movie, both meaning well and both making each other eventually happy.

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13. 50 First Dates

Adam Sandler sacrifices a normal life in order to help his one true love figure out who she is every single day after an accident causes daily memory loss.

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14. What’s Your Number?

Anna Faris fears that her craft hobby is too geeky, but Chris Evans doesn’t see it that way and proceeds to build display cases for her!

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15. Clueless

When Alicia Silverstone’s confidence is crushed after a work mistake, Paul Rudd comes to the rescue and builds her back up again.

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16. Ever after

Drew Barrymore’s character performs a grand gesture of love when, after being robbed by a gang, she is told she can leave with whatever she can carry and she valiantly tries to lift her boyfriend.

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17. The Wedding Singer

After buying his ticket on his friend’s credit card, what can Adam Sandler do but profess his love to Drew Barrymore, 30000 feet in the air, by singing her a song he wrote especially.

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18. Forgetting Sarah Marshall

Jason Segel is the perfect gentleman when he steals and takes down a topless photo of Mila Kunis in a bar that she has always regretted.

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19. Knight and Day

Tom Cruise spends a lot of time kidnapping Cameron Diaz, but she turns the tables when she kidnaps him in order for him to be able to see his parents again.

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20. Let Me in

A romantic but deadly gesture from Chloe Grace Moretz’s character when she tears apart the bullies who are frightening her best friend!

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21. Love & Other Drugs

Jake Gyllenhaal’s character changes his womanizing ways when Anne Hathaway gets sick, doing everything to find treatment for her.

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22. Overboard

Kurt Russell and Goldie Hawn finally reveal their love for each other by acting out a scene from a story that Russell had told her during the movie.

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23. 10 Things I Hate about You

Heath Ledger performs a romantic and hilarious version of Can’t Take My Off Of You for Julia Stiles, escaping capture at every turn!

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24. Beastly

In a modern twist on Beauty and The Beast, Alex Pettyfer’s character goes to school to show his newly beastly face and declares his love for Vanessa Hudgens rather than stealing a kiss to cure his curse.

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25. Drive Me Crazy

Adrian Grenier has some smooth moves in this film as he slides down a sculpture in a tuxedo to ask Melissa Joan Hart to dance!

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26. Hitch

Rather than using the stylish dance moves Will Smith taught him, Kevin James sees his loved one cannot dance and so he joins in with the goofy moves instead.

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27. Valentine’s Day

Eric Dane is a closeted gay athlete in love with Bradley Cooper, but to save his relationship and prove his love, he comes out in a public press conference.

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28. Titanic

In a film where the two lovers make plenty of sacrifices for each other, can there be a bigger gesture than making sure someone lives and you don’t?

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Of course, not all romantic gestures are appreciated or the love remains unrequited. That’s why this list doesn’t include the flash card scene from Love Actually, or John Cusack’s playing “their song” in Say Anything.