Romantic Comedies For Sad Singles and Cute Couples

While there are countless romantic comedies to watch any time of the year, here are the five most hilarious, comforting and legendary films to kick off Feb. 14.

With Feb. 14 just around the corner, love is in the air. Whether single, in a complicated situationship or celebrating a long-term relationship, it’s hard to ignore the heart-shaped candies and exaggerated declarations of love.

Valentine’s Day is characterized by all things romance — especially the movies. From enemies-to-lovers tropes to classic comedies, here are five rom-coms to cure the Valentine’s Day sadness or laugh about with your partner.

“10 Things I Hate About You”

When Cameron James (Joseph Gordon-Levitt) transfers to Padua High School, he is immediately infatuated with the school sweetheart Bianca Stratford. Unfortunately for Cameron, his crush has a strict father with a stricter house rule: Bianca can’t date until her older sister, Kat (Julia Stiles), does.

Cameron is willing to go to any extreme to win Bianca’s heart, even organizing a complex scheme to find a boyfriend for Kat, whose rebellious spirit often pushes people away.

Enter Patrick Verona (Heath Ledger), the long-haired, cigarette-smoking bad boy with a notorious reputation and charming Australian accent. When bribed by the most popular guy in school, Patrick agrees to date Kat for a large sum of money — but neither of them expect to fall in love. 

Press play for Ledger’s iconic performance of “Can’t Take My Eyes Off You” and stay for a heartwarming love story. This modern adaptation of Shakespeare’s “Taming of the Shrew” is an amazing film to laugh, cry and quote all year round. 


Will Smith stars as a professional matchmaker. (Courtesy of Columbia Pictures)

Will Smith stars in the 2005 film as dating consultant and professional matchmaker Alex “Hitch” Hitchens. Hitch meets celebrity gossip columnist Sara Melas (Eva Mendes) after being tasked with helping Albert Brennaman (Kevin James)  — a socially awkward client  — score a date with a famous socialite. As Sara seeks to uncover the truth behind Albert’s new relationship, her career sends her crossing paths with Hitch in the most unexpected ways. 

As they go from friends to enemies to lovers, Hitch and Sara’s comedic relationship and constant banter will chase away any Valentine’s Day blues. 

Crazy Rich Asians 

When Rachel Chu (Constance Wu) is invited to attend a wedding with her long-term boyfriend Nick Young (Henry Golding), she expects a lovely trip to Singapore, an abundance of good food and the opportunity to meet Nick’s family. What she doesn’t expect is for his family to be rich — crazy, filthy, inconceivably rich.

As an outsider to Nick’s world, Rachel must navigate his disapproving mother, snobbish ex-girlfriend and the expectations of holding a massive fortune, all while keeping her relationship afloat.

This film proves love is worth more than any amount of money, and true love will always find a happy ending.

The Wedding Planner

“The Wedding Planner” is both tearful and heartwarming. (Courtesy of Columbia Pictures)

When Mary Fiore (Jennifer Lopez) is hired to plan an extravagant wedding, she is shocked to find that the groom is Steve Edison (Matthew McConaughey), the mysterious doctor who swept her off her feet only nights before. 

Unaware of Mary and Steve’s connection, the bride leaves on a business trip, placing planning responsibilities on the pair. Left alone to plan a wedding, Mary and Steve can’t help falling for one another despite all the obstacles in their way. 

From ballroom dancing to chance encounters, “The Wedding Planner” is packed with both tear-jerking and heartwarming moments. 

Set It Up

Harper Moore (Zoey Deutch) and Charlie Young (Glen Powell) meet late one night in their office building — and they instantly hate each other.

Both are employees of demanding, selfish bosses who make their lives miserable on a daily basis. Desperate for relief from their difficult jobs, Harper and Charlie team up to set their bosses up on a date. Naturally, while setting up their bosses, they also set themselves up for love. 

Cliché rom-coms are a necessity on Valentine’s Day, and “Set it Up” is as cliché as it gets.

Featured image courtesy of Touchstone Pictures

Natalie Pitluck

Natalie Pitluck