20 Of The Best & Worst Summer Flings On Film

Photo: Moviestore/Rex/Shutterstock.
What is it about summer that gets us so hot and bothered? Is it the reduction in clothing? The vitamin D energy boost? The prospect of going on vacation and actually being able to seduce someone without smacking the snooze button and then sprinting to the office the next morning?
Maybe we all just crave a summer fling because it (usually) looks so damn irresistible on the big screen. Who hasn't fantasized about a sexy camp counselor, lifeguard, or chiseled dance instructor? Don't most flights and train journeys begin with a silent prayer that some stunning adventurer will be in the next seat? Aren't you the teensiest bit bummed when you return from a summer abroad with absolutely nothing to report?
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We get it. Just remember that, while many of these cinematic summer romances are worth pining after, there are plenty that turn out to be total duds. For every Baby and Johnny, there's a Lisa and Robbie. Sometimes you get a story to tell the grandkids. Sometimes you get a story to tell the judge.
Roll the tape.
1 of 21
BEST
Tony & Maria (Richard Beymer & Natalie Wood), West Wide Story
(1961)

Over the course of a few sweltering New York summer days, this aspiring Romeo and Juliet couple attempts to cross racial and cultural boundaries in the name of love. What results is one of the most touching, poignant, tragic depictions of first love ever seen onscreen, and set to music.
2 of 21
BEST
Princess Ann & Joe (Audrey Hepburn & Gregory Peck), Roman Holiday (1953)
These two really only had a day together, but oh, what a day it was. Everything's just a bit more glorious in Italy.
3 of 21
BEST
Frances & John (Grace Kelly & Cary Grant), To Catch a Thief (1955)
He's a cat burglar, she's a mischievous heiress...what could possibly go wrong? Shout-out to fireworks and the French Riviera for upping the romance factor.
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4 of 21
BEST
Sandy & Danny (Olivia Newton-John & John Travolta), Grease (1978)
We could do without Danny's sexual innuendos, but there's no denying that this summer fling was worth singing about on the bleachers.
5 of 21
BEST
Baby & Johnny (Jennifer Grey & Patrick Swayze), Dirty Dancing (1987)
The ultimate summer romance. Anyone else like to pretend that these two ran off together for real, with Baby joining the Peace Corps and Johnny adding local dances to his repertoire?
6 of 21
WORST
Lisa & Robbie (Jane Brucker & Max Cantor), Dirty Dancing (1987)
Lisa learned the hard way that her summer crush was a total sleaze. That'll teach him to not lock his cabin door.
7 of 21
WORST
Kat & Tim (Annabeth Gish & William R. Moses), Mystic Pizza (1988)
A big fat no to dating the married man who has hired you to babysit his kid.
8 of 21
BEST
Lloyd & Diane (John Cusack & Ione Skye), Say Anything (1989)
Proof that you can still get the girl after graduation, provided you have a trench coat and the right Peter Gabriel cassette tape.
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9 of 21
BEST
Wednesday & Joel (Christina Ricci & David Krumholtz), Addams Family Values (1993)
Paula Abdul said it best: Opposites attract.
10 of 21
WORST
Drew & Lauren (Larenz Tate & Jada Pinkett Smith), The Inkwell (1994)
Lauren was such a snob to poor Drew, though his decision to ditch her and lose his virginity to a married woman was only marginally better.
11 of 21
BEST
Céline & Jesse (Julie Delpy & Ethan Hawke), Before Sunrise (1995)
Raise your hand if you bought a Eurostar pass in hopes of finding your ultimate scruffy soulmate.
12 of 21
BEST
Lucy & Osvaldo (Liv Tyler & Ignazio Oliva), Stealing Beauty (1996)
If you're determined to lose your virginity, the Tuscan countryside in summertime is as good a place as any.
13 of 21
BEST
Annette & Sebastian (Reese Witherspoon & Ryan Phillippe), Cruel Intentions (1999)
Things didn't really work out for these two (ahem), but it's still hard to not be swept up by their end-of-summer crushing and Counting Crows-soundtracked lovemaking.
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14 of 21
BEST
Ben & McKinley (Bradley Cooper & Michael Ian Black), Wet Hot American Summer (2001)
This clandestine hook-up happily resulted in a wedding by the lake. Isn't summer camp amazing?
15 of 21
WORST
Tamsin & Mona (Emily Blunt & Natalie Press), My Summer of Love (2004)
Sorry, but discovering that your lover is a big fat liar with some serious issues overshadows the fact that she has great taste in music.
16 of 21
BEST
Lena & Kostas (Alexis Bledel & Michael Rady), The Sisterhood of the Traveling Pants (2005)
This summertime fling was like a Greek version of Romeo & Juliet, minus everyone dying.
17 of 21
WORST
Cristina, Juan & María Elena (Scarlett Johansson, Javier Bardem & Penélope Cruz), Vicky Cristina Barcelona (2008)
Okay, so the sex was hot. Ultimately, however, Cristina realized that hooking up with a lothario and his temperamental ex-wife was more trouble than it was worth. And that was before her friend Vicky almost got shot.
18 of 21
BEST
James & Em (Jesse Eisenberg & Kristen Stewart), Adventureland (2009)
Despite Ryan Reynolds's evil intentions, these theme-park employees just can't quit each other.
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19 of 21
BEST
Sam & Suzy (Jared Gilman & Kara Hayward), Moonrise Kingdom (2012)
In which two 12-year-olds who are far cooler than they have any right to be make us feel all nostalgic and wistful about young love.
20 of 21
WORST
Leigh & Jason (Kristen Bell & David Lambert), The Lifeguard (2013)
Long story short: She's 29. He's in high school. Can't even type that without picturing a group of Wendy Williams audience members booing in outrage.
21 of 21
WORST
Franck & Michel (Pierre Deladonchamps & Christophe Paou), Stranger by the Lake (2013)
Is mind-blowing sex with a sexy Frenchman worth potentially being murdered? Non.
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