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For the child-at-heart

Edward Scissorhands (1990)—A fairytale in every sense, this Tim Burton masterpiece introduced a post-21 Jump Street Johnny Depp to moviegoers the world over. Though a Frankenstein-in-suburbia fantasy, Edward’s journey to love has a true beating heart that uses wit and wonderment to resonate with anyone who’s ever felt like an outsider.

For the classicist

Casablanca (1942)—Considered one of the greatest films of all time, this melodrama puts Humphrey Bogart and Ingrid Bergman in two corners of a love triangle backlit by the explosions of WWII. With charisma and swagger to spare, Casablanca will immerse you neck-deep in heartache, saloon pop and Nazis.

For the curmudgeon

As Good As It Gets (1997)—Jack Nicholson plays an eccentric genius/cynic in this romantic comedy about a successful romance novelist who has a lot to learn about real life. Helen Hunt, Greg Kinnear and Cuba Gooding Jr. all have a hand in Nicholson’s painful awakening.

For the punk

Sid & Nancy (1986)—If you can claw through the abrasive personalities, painful memories and drug addictions to reach for romance, you’ll have made the same journey that Sex Pistols bassist Sid Vicious and American girlfriend Nancy Spungen made in real life—a morbid search for love, before tragedy and excess overwhelmed them both.

For the neurotic

Annie Hall (1977)—Woody Allen at his bittersweet zenith. The satiric subtitles let viewers know what Allen’s comedian and Diane Keaton’s free spirit really have on their minds in this comedy that manages to address social stereotypes and lampoon them at the same time.

For the single friend

When Harry Met Sally (1989)—Rob Reiner doing his best Woody Allen. Billy Crystal and Meg Ryan are acquaintances, friends, foes and sweethearts in the film that asked the question, “Can a man and a woman be friends, without sex getting in the way?” Ryan’s now classic deli performance was a first, too.