Five Romantic Comedies to Revisit for Valentine’s Day

By Cate Tarr | Photo by Phillip Goldsberry on Unsplash

The ’90s up to the 2010s were a goldmine for romantic comedies — “Notting Hill” or “My Best Friend’s Wedding,” anyone? We selected some tried-and-true flicks to watch again (or for the first time!) for your Valentine’s Day festivities — however you celebrate.

“While You Were Sleeping” (1995)

“While You Were Sleeping” is a story about fate. Sandra Bullock’s character, Lucy, works as a ticket booth operator for the Chicago Transit Authority. When her longtime crush and daily train commuter, Peter (played by Bill Pullman), falls on to the track one morning, Lucy jumps to save him without hesitation. After taking him to the hospital, she not only learns that Peter is in a coma, but she now has to explain her relationship with Peter to his entire extended family. Miscommunication ensues that she’s Peter’s fiancé, and Lucy finds herself stuck in a web of lies. Containing charming characters, relatable moments and an inventive love story, this film keeps you on the edge of your seat.

Sleepless in Seattle” (1993)

Culminating in an event that takes place on Valentine’s Day, “Sleepless in Seattle” is certainly on-point. And despite its romantic plot, the two leads, Meg Ryan and Tom Hanks, never interact with each other in person until the end of the film. During a national call-in radio show Allie Reed (played by Ryan) hears Sam Baldwin (Hanks) talk about how much he misses his wife, Maggie, who died from cancer. Reed, who lives in Baltimore, feels inexplicably touched by his words — which reveals her dissatisfaction with her own romantic relationship (which, by the way, her fiancé is played by Bill Pullman!).

After Baldwin’s radio spot, women from all over the country start sending letters to his Seattle home, confessing their love. As his young son Jonah sifts through these letters, Reed’s letters stand out to him. A unique series of events follows in which the two characters find their way to each other — despite living on opposite coasts.

“Crazy, Stupid, Love.” (2011)

With a plot of two tales that intertwine and result in an amusing turn of events, “Crazy, Stupid, Love.” doesn’t disappoint. After Steve Carell’s character, Cal Weaver, learns that his wife wants a separation, he heads to a bar to drown his sorrows. Spotting Weaver, Jacob Palmer (played by Ryan Gosling) — a smooth-talking, well-dressed ladies’ man — chats him up and determines that he must give Weaver a makeover. The film is funny and heart-warming, and illuminates the value of family and fighting for your love.

“Bridget Jones’s Diary”  (2001)

Bombarded with romantic expectations from her family at an annual holiday gathering, Bridget Jones (Renee Zellweger) is fed up with her life. Instead of falling back into her tired patterns and being single, Jones decides to turn over a new leaf: stop smoking, lose weight and find a man. Confronting inevitable obstacles along the way (including a cheating boyfriend), she learns to embrace not only the type of guy she truly wants to be with, but also the type of man she deserves. Also starring Colin Firth and Hugh Grant as her love interests, the film is funny and inspiring.

“The Proposal” (2009)

Margaret Tate (Sandra Bullock) is a sophisticated and career-minded woman. However, she encounters a wrinkle at work when her boss informs her that her visa is expired and she’ll be deported to Canada in a matter of days — which means she’ll lose her job. Thinking quickly, she convinces her assistant, Andrew Paxton (played by Ryan Reynolds), to marry her in exchange for a promotion (yikes). Of course, if they’re engaged, they have to go and meet Paxton’s family, right? So they travel to Alaska where his family is based to prove to authorities that the marriage is indeed legitimate. And, since it’s a romantic comedy — we’ll let you draw a conclusion on what happens next.

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