Source: WebMD
Breakfast at Tiffany’s (1961)
Holly Golightly is a party girl and aspiring socialite who's looking for her sugar daddy. Her new neighbor, Paul Varjak, is an aspiring writer and the kept man of a wealthy older woman. Neither one is looking for true love, but between wild parties and early-morning trips to gaze in the windows of Tiffany's, the two fall for each other.
“I still cry at the end when Audrey is looking for Cat in the rain!” – WebMD member Trez43
When Harry Met Sally (1989)
Harry (Billy Crystal) and Sally (Meg Ryan) have been friends for years. But a question hangs between them: What would happen if they slept together? It’s that sexual tension – the "will they or won’t they?" – that makes When Harry Met Sally so compelling.
"Billy Crystal isn't handsome like George Clooney, but you know he's the one. And maybe in the end that's what makes it so wonderful." – WebMD member tenuli
The Way We Were (1973)
Though differences in outlook and personality are what initially attract the intense Katie and the WASP-y, sheltered Hubbell (the chemistry between Redford and Streisand is undeniable), ultimately these differences prove too much for them to overcome.
"The final scene gets me every time: Katie and Hubbell run into each other years after they've split. He has a glamorous new woman on his arm. She tells him, wistfully, 'Your girl is lovely, Hubbell.'" – WebMD programmer Florrie Byrd
Harold and Maude (1971)
Harold is young, rich, and obsessed with death. That all changes when he meets Maude, a spunky septuagenarian with a zest for life. An unlikely love affair develops between the two, and while there’s the potential for ickiness (he’s 20, she's nearly 80) instead the romance between them is incredibly tender and believable.
"One of the sweetest, most touching love affairs on film. It proves the old adage 'love is blind.'" – WebMD video producer Sandee LaMotte
Love Story (1970)
Have plenty of Kleenex handy when you sit down to watch Love Story. The final line uttered by Ryan O'Neal’s character, Oliver Barrett, pretty much sums it up: "What can you say about a 25-year-old girl who died? That she was beautiful and brilliant? That she loved Mozart and Bach, the Beatles, and me?"
"My favorite is the 1970 classic Love Story. It is heart-wrenching, but you can feel the love they share." – WebMD member chrisymay003
The Lake House (2006)
Kate (Sandra Bullock) and Alex (Keanu Reeves) strike up a correspondence after she moves into the lake house he once occupied. Through letters, a romance begins to grow between the two. Only problem – he's living in 2004, and she’s living in 2006. It's an implausible premise, but a passionate story and charismatic leads make it memorable.
"I am a hopeless romantic and have always wished someone would love me that much." – WebMD member MelanieJoy
Roman Holiday (1953)
While on a tour of European cities, bored and sheltered Princess Ann (Audrey Hepburn) gets a taste of the freedom she's always longed for with American reporter Joe Bradley (Gregory Peck). The two fall in love during a whirlwind day exploring Rome. Alas, duty calls, and the two must part ways. The romance wasn't meant to be, but the movie is no less romantic for it.
"One of the best ‘but it could never be’ stories ever." – WebMD program manager Michelle Howard
Sleepless in Seattle (1993)
Tom Hanks is Sam, a widower whose young son schemes to find him love by putting him on a national radio talk show. In New York, Ryan's character, Annie, hears the broadcast. She's smitten. Missed connections and mad dashes ensue. When the two finally meet at the top of the Empire State Building, it's true love.
"This movie's great because the archetypal nice-guy, Tom Hanks, comes out victorious and finds the woman of his dreams." – WebMD programmer Brian Stanga
Doctor Zhivago (1965)
Set against the backdrop of the Russian Revolution, Doctor Zhivago tells the tale of surgeon-poet Yuri Zhivago, who is torn between his devoted wife and the beautiful Lara (played to perfection by Julie Christie). It's an age-old dilemma: Do you choose fidelity and stability, or passion and inspiration?
"Omar Sharif was the first 'older man' I ever lusted after." – WebMD writer Jeanie Davis
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