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Every once in a while, you find yourself needing to do some wooing (perhaps even on some evening next week). Sure, you’re great at gift giving and a pro at the art of the love letter.

But sometimes, the situation calls for something bigger—a little more intricate, Cary Grant–level wooing. And where does any self-respecting gentleman worth his weight in rose petals get a little inspiration? Why, the cinema, of course.

So to help you out, the Kempt Guide to Cinematic Grand Gestures—ranked by degree of difficulty.

 
The Movie: Love, Actually

The Setup: A hopelessly romantic man just has to get something off his chest. He does so with nothing but some sweet nothings written on cue cards while a CD of gentle Christmas carols tolls gently.
Degree of Difficulty: Nearly none, assuming you’re literate and live in a town with an OfficeMax. (We’re ignoring the context here: the object of his affections is married to another man. If that’s the case, you’re on your own.)

 
The Movie: Say Anything…

The Setup: Lloyd Dobler: a genius and an impossible ideal wrapped up in a trench coat. His scenario is similar: oversized boom box, cassette copy of Peter Gabriel’s So, bedroom window.
Degree of Difficulty: Low, if you know her pretty well (otherwise, this reads as a little more stalker-ish). Your biggest hurdle here is going to be finding a cassette copy of So.

 
The Movie: 10 Things I Hate About You

The Setup: Before his more serious days, Heath Ledger once hijacked a full-on marching band, interrupted a soccer practice and evaded security forces so he could belt out a serviceable version of “I Love You, Baby” in front of an entire high school, all to woo Julia Stiles.
Degree of Difficulty: High, unless you’re a high school band instructor. Now, this idea has lots of variants, but please note: it is the policy of this blog to recommend you think long and hard before attempting any sort of public musical surprise.

 
The Movie: The Wedding Singer

The Setup: Robbie Hart (Adam Sandler), with the help of Billy Idol, commandeers the intercom of a 747 to sing an original song to the woman he loves before she marries Mr. Wrong.
Degree of Difficulty: Low, until you get slam-tackled by an undercover TSA agent. You also need to know Billy Idol.

 
The Movie: Rushmore
Rushmore
The Setup: After Max Fischer causes a scene at dinner with the love of his life, his teacher Miss Cross, Max tries to apologize to her by breaking ground on an aquarium. On the baseball diamond, on school property.
Degree of Difficulty: His head’s in the right place here with the “I don’t give a shit about the barracudas… I’m building it anyway” attitude. But the rest of it wavers between ill-advised and impossible.

 
The Movie: Notorious

The Gesture: Hitchcock is mostly known for suspense and a creepy thing for blondes. But here he gives us one of the grander gestures in cinematic history. Ingrid Bergman is caught in a love triangle with a dashing government agent (Cary Grant) and her Nazi husband. When said Nazi poisons Bergman, Grant saves the day by kicking down the door of her mansion, scooping her out of her deathbed and carrying her down the long, winding staircase as the Nazis point their guns at him.
Degree of Difficulty: Uh, as a best practice, unless you’re Cary Grant or Indiana Jones, try not to fall in love with a lady involved with a Nazi poisoner.

—M.S.

CONTRIBUTORS

  • Mark Schectman