Movies say go big or go home

Romantic comedies teach that simply saying I love you is not enough. You need to make a grand romantic gesture to win someone's heart.

The classics: boomboxes and stadium songs

In Say Anything, John Cusack holds a boombox over his head outside his ex's window. In 10 Things I Hate About You, Heath Ledger sings and dances in a high school football stadium.

More recent films push it further

Ryan Gosling hangs from a Ferris wheel threatening to let go unless his love interest agrees to a date in The Notebook. Kathryn Heigl jumps onto a departing wedding boat in 27 Dresses.

Real life is not the movies

Grand gestures that look romantic on screen would raise concerns in reality. Having someone risk arrest, throw themselves in front of a car, or sacrifice their career puts enormous pressure on you.

Dan Pink's regret research

Author Dan Pink collected over sixteen thousand regrets from people globally. Many involved not pursuing romantic interests boldly enough, with some regretting inaction for ten, twenty, even forty years.

The train in Belgium

One man met a woman on a train and spent an amazing ride together. When they reached her stop in Belgium, she said no to him getting off. They kissed, exchanged addresses, and never met again.

“The man told Dan he has always regretted not getting off the train with her in Belgium 40 years ago.”

The other side: pressure to say yes

Research shows people underestimate how hard it is for others to reject them, especially during grand romantic gestures. A bold public display makes it even harder for someone to say no.

Heath Ledger got it right

In 10 Things I Hate About You, Heath Ledger's character performs an embarrassing song and dance routine, making himself vulnerable. Crucially, he runs off afterward without asking her to respond publicly.

Kathryn Heigl's speech works too

In 27 Dresses, Kathryn Heigl boards a boat and commandeers the DJ's microphone to declare her feelings. She ends with, That's it, that's all I had to say, before walking off without demanding a response.

“That's it, that's all I had to say.”

The key difference: amends, not persuasion

Good romantic gestures repair hurt or reassure commitment. Bad ones try to persuade someone to feel something they have already said they do not feel. Respect for autonomy is what separates them.

The man on the train did it right

By giving the woman his address and leaving the choice to her, he went for it while respecting her autonomy. Wishing things had turned out differently does not mean he should have pursued her more aggressively.

“That's the trouble with grand romantic gestures; they can make respecting someone's wishes look like giving up too easily.”