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Roman Holiday (1953)
Starring: Audrey Hepburn, Gregory Peck
She (Hepburn) is a sheltered European princess who decides to slip free of her strict guardians for a night off during a royal tour stop in Rome. He (Peck) is an American reporter who finds the princess heavily sedated and passed out on a bench (her doctor gave her a sleeping pill so she could rest up and fulfill her busy schedule of royal duties the next day). The journalist secretly arranges to have their day out photographed for a splashy exposé, but the two have undeniable chemistry. Will he still exploit the princess’ secret to further his own career?
Breakfast at Tiffany’s (1961)
Starring: Audrey Hepburn, George Peppard
Paul Varjak (Peppard) becomes fascinated with his new neighbor, Holly Golightly (Hepburn), a mysterious, elegant party girl who lives in his New York City building.
Harold & Maude (1971)
Starring: Ruth Gordon, Bud Cort
This May-December romance movie about an introverted teen (Cort) finding love with a septuagenarian (Gordon) was a critical and box-office flop, but has gone on to become a cult classic.
Annie Hall (1977)
Starring: Diane Keaton, Woody Allen
Alvy Singer (Allen) tries to figure out why he and Annie Hall (Keaton), who seems like the perfect woman, just can’t make it as a couple.
When Harry Met Sally... (1989)
Starring: Meg Ryan, Billy Crystal
The first time they meet, they hate each other. The next, it’s a cold animosity. Then, they become best friends. Add in an iconic fake orgasm in a deli and see if this movie can answer the all-important question of whether or not a man and woman can ever just be friends.