Eight Timeless RomComs That I Recommend To Watch On Valentine’s Day

Clueless (1995)

As if! Based on Jane Austen’s Emma, this Valley Girl classic starring Alicia Silverstone is filled with not only unexpected love, but the way friendships can evolve over time. The clothes! The quotes! This timeless film is well worth at least one annual screening.

Roman Holiday (1953)

Audrey Hepburn flexes her serious talent as a bored Princess Ann, who gives her guardians the slip for an adventure with American newsman Joe Bradley (Gregory Peck) in this romantic comedy classic. You may already know the iconic scooter scene that basically created the trend of tooling around city streets in a Vespa.

You’ve Got Mail (1998)

Some of the technology in this late ’90s standard might be charmingly old-school, but the message goes the distance. Tom Hanks and Meg Ryan have starred in three films together, but You’ve Got Mail — a riff on the classic The Shop Around the Corner — really makes the most of their undeniable onscreen chemistry.

Pretty Woman (1990)

Julia Roberts and Richard Gere make a really cute couple, but Roberts’ antics are what really earned this one its place in history. “Big. Huge.” became part of our lexicon after watching the scenes of her shopping in Beverly Hills and no polo match feels complete without Roberts stomping divots.

Forgetting Sarah Marshall (2008)

Peter (Jason Segel) takes a trip to Hawaii to heal from a breakup. But then his ex Sarah (Kristen Bell) shows up at the same resort. This heartwarming comedy of errors shows that even the worst possible circumstances can work out just fine by the time the credits roll.

The Proposal (2009)

The overbearing Margaret (Sandra Bullock) pretty much forces her employee Andrew (Ryan Reynolds) to marry her so she can avoid deportation to Canada, which is awkward enough. But when they visit his family in Alaska, sparks start to fly in the snow. If the gorgeous Alaskan setting isn’t enough for you, check out Betty White‘s turn as Andrew’s lovably risqué grandma.

My Big Fat Greek Wedding (2002)

Pass the Windex, bake a bundt and tune in to watch a woman (Nia Vardalos) from a very, very Greek family fall in love with a non-Greek man (John Corbett). Romance is a family affair in this movie that shows how you really do marry your in-laws, especially if their personalities are stronger than Sambuca.

Serendipity (2001)

Jonathan (John Cusack) and Sara (Kate Beckinsale) spend one amazing night together in New York City, but then fall out of touch for years afterward. As they prepare to marry other people, they both get cold feet and decide to hunt each another down instead. If you don’t believe in fate, let this classic change your mind.

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