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Ben & Elaine (Dustin Hoffman & Katharine Ross)
The Graduate (1967)
Okay, so the brilliant thing about this film is that in its final moments, it actually points out the obvious fucked-up-ness of this relationship and its inevitable demise. Elaine has just abandoned her newly minted husband at the altar to run off with Ben, who's been sleeping with her mother. They hop on a bus, giddy with adrenaline — but as the reality of what they've just done sets it, their smiles fade and "The Sound of Silence" plays. Just like that, the thrill is gone.
Sandy & Danny (Olivia Newton-John & John Travolta)
I have distinct memories of watching this movie as a child — specifically, loving every minute of it until the bewildering finale. Even 9-year-old me was like, WTF, Sandy?! After her complete 180,
Sandy would definitely come to resent Danny for the fact that she gave up her identity to be the sexy badass he wanted.
Andie & Blane (Molly Ringwald & Andrew McCarthy)
Pretty in Pink (1986)
If this pairing didn't sit quite right with you, there's a good reason: The ending was originally written with Andie and BFF Duckie facing the rich kids together and dancing to David Bowie's "Heroes." But that didn't test well with audiences, so they re-shot it with Andie choosing the rich (but bland) pretty boy, Blane — a "historic wrong that will never be completely righted," according to Jon Cryer (who played Duckie). Plus, high school romances tend to fizzle out a couple of months after graduation, anyway.
Baby & Johnny (Jennifer Grey & Patrick Swayze)
Dirty Dancing (1987)
There are a few factors working against these two, despite their sweaty chemistry. Baby was on track for for college and the Peace Corps. She doesn't seem like the kind of girl to just throw her life-plans out the window. Long-distance would've been rough, too. Remember, this is the '60s — no FaceTime! And the plain truth is, in the '60s, your family's approval and finding a mate in the same socioeconomic class were much bigger factors than they are today.
Keith & Watts (Eric Stoltz & Mary Stuart Masterson)
Some Kind of Wonderful (1987)
Masterson herself said the cutesy ending with the diamond earrings is out of character. “This materialistic aspect is not who Watts is. She’d have walked away victorious...right to the pawn shop," the actress told Entertainment Weekly. (It's not surprising to learn that the ending of Wonderful is actually a form of wish fulfillment for screenwriter John Hughes, who didn't get the resolution he wanted with Pretty In Pink.)