8 Must-Watch Movies Like The Proposal

For millennials of a certain age, this ‘90s reimagining of Shakespeare’s The Taming of the Shrew is the ultimate teen comedy. Julia Stiles plays Kat, the sardonic teen with a fearsome reputation among her classmates for taking zero nonsense from gross boys and bitchy girls. Her sister, Bianca, is popular and gorgeous and banned from dating until Kat does, which seems as likely to happen as a cold day in hell. 

So, Bianca's prospective love Cameron decides to grease the wheels and set Kat up with Patrick Verona, the school’s enigmatic bad boy, played by the late great Heath Ledger. It seems impossible, but maybe there’s something special to be found between the sharp wit and sparks that fly between him and Kat.

Sandra Bullock was the rom-com queen for many years for a reason. Few actresses do klutzy stubbornness and charm quite like her. In Miss Congeniality, she plays Gracie, an FBI agent more comfortable beating up bad guys than wearing heels. 

After the Miss United States pageant is targeted by a mysterious terrorist, she’s forced to go undercover as a beauty queen and navigate the world of bikini waxes, tiaras, and praying for world peace. She’s aided by a cynical pageant guide and a crew of leering agents, but it’s her colleague Eric (Benjamin Bratt) who proves to be the most infuriating (and alluring) of the pack.

The 27 dresses of the title refer to the many bridesmaid outfits that Jane Nichols (Katherine Heigl) has worn over the years. She's the perennial bridesmaid to her many friends, but never the bride. The man she yearns for, her boss George, has just fallen hard for Jane's flighty sister Tess. 

Before she can don dress 28, Jane meets Kevin, a writer who is fascinated by Jane and thinks she'll make for a great article. They grow closer even as she remains unaware of his true intentions and hopes to find a way to scupper her sister's wedding. Is George the one, or is Kevin worth a second glance?

Who doesn't love a romance with a marriage of convenience at its center? In Peter Weir's Green Card, an American woman and a boorish French man decide to get hitched in the hopes of fixing their problems. Bronte (Andie MacDowell) rents the apartment of her dreams but lies about having a husband to get it. 

When immigration services start snooping for proof of his existence, she ropes Georges (Gérard Depardieu), a waiter in need of a green card, into a fake romance. They've got two days to fake the perfect relationship or he'll be deported and she'll lose her home. They're total opposites, but love always finds a way.

It’s tough to deny the irrepressible charm of Will Smith, and Hitch is a sadly rare opportunity to see him use that legendary charisma in a rom-com rather than for fighting aliens. Smith stars as the eponymous Alex "Hitch" Hitchens, a professional dating expert who coaches hapless men in the lost art of courtship. 

His latest assignment is Albert (Kevin James), who is smitten with a client at his investment firm, the seemingly out-of-his-league Allegra. That's easy stuff compared to Sara, a gossip columnist played by Eva Mendes, who suddenly captures Hitch's interest. The only problem? None of his techniques seem to work on her. Can he win her over by, shock horror, being himself?

Few romantic comedies defined the ‘90s quite like How Stella Got Her Groove Back. Based on the best-selling book of the same name by Terry McMillan, it catapulted Taye Diggs into stardom with his debut film role. The legendary Angela Bassett is the eponymous Stella, a single mother and career woman who takes a vacation to Jamaica at the behest of her friends, who chastize her for having zero romance in her life. 

While there, she meets Winston Shakespeare, a gorgeous local who is twenty years her junior. She's all in on a holiday fling, but it soon becomes apparent that the connection between the two of them goes well beyond a one-night stand on the beach. Yet Stella fears her chance at long-term happiness is dead in the water. Can she find a place in her busy life for Winston or will their love end when she leaves the island?

The legendary Queen Latifah is a celebrated actress as well as a rapper, and a super-underrated rom-com star to boot. In Just Wright, she plays Leslie, a physical therapist who works with top athletes. Every guy she meets thinks she’s great but sees her more as friend material than the ideal girlfriend. 

When she meets Scott, a star basketball player for the Nets played by Common, they quickly become friends, but things grow complicated when Leslie's god-sister sets her sights on becoming an NBA trophy wife. Leslie helps Scott through a major injury that could kill his entire career, but will he ever see her in the romantic light she craves?

If you want a proper golden age, old-school romantic comedy then you just can’t beat the magic of The Philadelphia Story. The one and only Katharine Hepburn plays a socialite who is getting ready to marry for the second time. Jimmy Stewart is a journalist eager to cover the social event of the year, and Cary Grant plays Hepburn's ex-husband. Neither, of course, was invited to the wedding—but both seem to appeal to Hepburn in ways her current beau do not. 

Made in 1940, The Philadelphia Story is as fresh and witty now as it was 80 years ago. With three endlessly charming leads and countless quotable lines, you won't regret cozying up with this film.