The Damn Good Dating Advice Hidden in 10 Summer Rom Coms

From nailing the first kiss to getting out of the doghouse

May 24, 2018 9:00 am

This is but one installment of 37 Things a Man’s Gotta Do This Summer, our annual compendium of everything worth seeing, doing, eating, drinking and generally making time for in your neck of the woods between now and September. Stay tuned all month for more.

Summer love.

Where does our fascination with the concept come from? Surely the phenomenon predates songs and movies.

Maybe its a function of its transience: as the season’s end draws nearer, days get shorter. Farewells draw nearer. Vacations march inexorably back toward reality. And in those fleeting moments, love is realized.

If you don’t kiss her on the beach, or chase her through the airport, or dab that rogue dollop of ice cream off her cheek tonight, then when?

So as  summer commences, it helps to have a refresher on how to play your cards right. Here to help you put your best foot forward, no matter the result? Dating lessons, reminders and takeaways from 10 essential summer rom coms.

Godspeed, aspiring lotharios.

Lesson 1: Avoid the bar fight at all costs
(500) Days of Summer

More often than not, the “this guy’s besmirched my lady’s honor, I must defend her” barside fisticuffs have very little do with the lady, and everything to do with a weak man’s ballooning insecurities. As Tom Hansen (Joseph Gordon-Levitt) learns when throwing a punch for Summer Finn (Zooey Deschanel), she took no pleasure in his presumed exploit. And he’s stuck with the stinger.

Lesson 2: Treat every kiss like it’s the first
50 First Dates

Does zoologist Henry Roth (Adam Sandler) have some moves or what? At the end of each day, he manages to steal a “first” kiss from amnesiac Lucy Whitmore (Drew Barrymore), to which she replies, “There’s nothing like a first kiss” every single time. Sunsets, stars and ukuleles are usually involved. Not a bad idea to adopt his lead into your game, whether you’ve just met someone, or are deep in the thick of it.

Lesson 3: Summer jobs are the one time it’s OK to dip the pen in company ink

Adventureland is one of those movies that (in a compelling way) seems unfathomably bored by its own content. The idea of a “purgatorial summer” has much in common with the unceasing cadence of any workplace, where people must imagine, or actually conjure, their own fun. Decide for yourself whether James Brennan’s (Jesse Eisenberg) tortured expressions and unsaid soliloquies — which all, yes, stemmed from work are worth it in the long run.

Lesson 4: Own your pratfalls

Hitch (Will Smith) ends this iconic film by looking straight at the camera and saying “Basic principles … there are none.” He then unleashes a winning grin and heads off to join in one of the greatest wedding dance sequences in cinematic history. This is a man whose entire life/dating philosophy just got flipped on its head. And he’s adapted like a champ. Own your miscues, your trips, your allergic reactions — goofiness has its own charm.  

Lesson 5: Take note of the little things
Friends With Benefits

Grand Central grand gesture? Great. But it won’t get off the ground if you weren’t listening in the first place. Stuck in the doghouse, Dylan Harper (Justin Timberlake) goes way back into the vault to his first few meetings with Jamie Rellis (Mila Kunis), referencing little things that were special to them, like noticing she blinks every time she swears … and of course the whole “Closing Time” bit. It’s a concept straight ripped from When Harry Met Sally (that’s a quad-seasonal rom com, the best kind), but that just means it’s evergreen and true.

Lesson 6: Some things are more important than the game
Summer Catch

“Staht the cah!” So you’re on the mound, two outs away from ending the best pitched Cape League game in recent memory, with scouts in attendance and the weight of your relationship with your dad and a MLB dream on your shoulders …. and you’re thinking of a girl? You’ve simply gotta go take care of business. And that’s exactly what Ryan Dunne (Freddie Prinze Jr.) does.

Lesson 7: Aim for someone your own age (or at least within a decade)
Something’s Gotta Give

“After a heart attack … once you can climb a set of stairs, you can have sex.” So Doctor Mercer (Keanu Reeves) instructs Harry Sanborn (Jack Nicholson), the man with eyes only for women under half his age. This film expands on the society’s general disdain for romantic age gaps, by positing: younger isn’t just disreputable, it’s dangerous. After all, what are you proving, running around like that? Find someone you can talk to; you’ll last far longer.

Lesson 8: Dot some Is and cross some Ts
Can’t Hardly Wait

Letters will give you an undeniable edge simply because everyone else is too lazy to write ‘em. A letter certainly gives Preston Meyers (Ethan Embry) the leg-up in his desperate pursuit of Amanda Beckett (Jennifer Love-Hewitt), a popular gal who breaks up with a jock at a party. Within five minutes, the entire school of boys is propositioning her. But Preston took the time to write a note, and well, things work out.

Lesson 9: If you have a “In case we’re both single, let’s get married at such and such age” pact …
My Best Friend’s Wedding

YOU’RE BOTH FULL OF IT. If you have a “song” with a “best friend,” please go buy a ring. Good day!

Lesson 10: Own up to skills you simply do not have
One Crazy Summer

This buzzed-out flick finds Hoops McCann (John Cusack) failing to live up to his regrettable name (pops was a basketball star, naturally). And yet, he still attempts to stunt during a misadventure in Nantucket when he has a run-in with Cassanda Eldridge (Demi Moore). Obviously, he’s exposed. If you have any intentions of being with a girl, claiming skills at the outset will inevitably A) lead to requests for a performance or B) come to light … painfully. Neither outcome is ideal.

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