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The Gentleman’s Guide to Grand Romantic Gestures

Six Hard-and-Fast Rules to Pulling Off the Perfect Valentine’s Day Stunt

By Sam Eichner ·
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Photo: New Line Cinema

Throughout history, lovers have used grand romantic gestures to demonstrate just how far they’re willing to go to win the adoration of their respective paramours.

A war was waged over Helen of Troy.

Mughal emperor Shah Jahan commissioned the Taj Mahal to house the tomb of his favorite wife, Mumtaz Mahal.

Gucci Mane proposed to Keyshia Ka’oir in front of an entire stadium at an Atlanta Hawks game.

This February 14, it’s your turn. And to aid you in your noble quest, we’ve created a quick primer, comprised of six hard-and-fast rules to pulling off the perfect Valentine’s Day stunt.

In the words of Mr. Mane himself, “You a dancer, on the camera/In the G-string, girl I want you/At my concert, at the condo/In my bedroom, in the guestroom.” 

We’re not sure how exactly that applies. Anyway, here’s that primer now.

Rule #1: Grand romantic gestures are in the tiniest details.
When planning your grand romantic gesture, start small: is there something you know about them that nobody else knows? Do they have any unique or uncommon likes or dislikes? Do you share an inside joke about, say, drunkenly making out with a second cousin? Weird example, but you get the picture. Executing a grand romantic gesture is like writing a good short story: start with something seemingly insignificant, and raise the stakes.
The Case Study: Hal creates a giant whale silhouette in the snow for Claire Bonner, because he believes it’s her favorite animal. However, her favorite animal is a zebra. Like we said: it’s in the details. Also, yes: this was an actual Snow Day reference.

Rule #2: Manufacture a sense of urgency.
The more urgent the gesture, the more dramatic it is, the greater the effect. Your attitude should lie in the collision between desperation and desire.
The Case Study: When Ryan Gosling hangs from a Ferris wheel until Rachel McAdams agrees to go out with him in The Notebook.

Rule #3: Timing is everything.
Love is about timing as much as it is about... love. Does that make sense? Let’s presume it does, and suffice it to say that when planning your grand romantic gesture, the “when” is just as important, if not more so, than the “what.”
The Case Study: When Dustin Hoffman interrupts the wedding in The Graduate. That was a close one.

Rule #4: Know your audience.
This is true for any performance, but doubly so for a grand romantic gesture. Some may prefer glitz, glamour, pizzazz; others may prefer something a little more low-key; others still may not want you to perform a romantic gesture at all. This is especially true for exes and people you haven’t met before. So, know that.
The Case Study: Adam Sandler singing a song to Drew Barrymore, aka the future Ms. Julia Gulia, in The Wedding Singer. As we learned throughout the movie, the betrothed is powerless to resist Sandler’s middling musical talent.

Rule #5: Don’t take yourself too seriously.
The best romantic gestures should make your paramour laugh, then cry, then do that whole laugh-cry thing where their entire face just sort of comes undone in an unsexy flood of snot and tears. 
The Case Study: Heath Ledger’s rendition of “Can’t Take My Eyes Off You” on the bleachers in 10 Things I Hate About You.

Rule #6: Grand romantic gestures don’t have to be... grand.
We know. That sounds slightly oxymoronic. But sometimes the grandest romantic gestures are simply the most thoughtful.
The Case Study: And now, here’s Colin Firth punching Hugh Grant in the face for love in Bridget Jones’s Diary. We were getting a little sappy there for a moment.

The original version of this article was published on January 24, 2017. 

Sam Eichner likes literature, reality television and his twin cats equally. He has consistently been told he needs a shave since he started growing facial hair.

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