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Five rom-coms perfect for Valentine’s Day viewing

Rose,Wife of Bath,バラ,ワイフ オブ バス, by T.Kiya / CC BY-SA 2.0 

Valentine’s Day is rapidly approaching, so whether you’re planning a movie night with your boo or a solo candy binge, you’re going to need something to watch. Here are five of the best romantic comedies to set the mood for the most romantic day of the year. 

1. “Cha Cha Real Smooth”


The breakout hit out of last year’s Sundance Film Festival, “Cha Cha Real Smooth” is an unorthodox yet endlessly heartwarming coming-of-age romantic comedy from writer/director/star Cooper Raiff. If you’re feeling a little lost in life, this will hit you like a truck. Come for the chemistry between Raiff and co-star Dakota Johnson, and stay for an entire reconceptualization of what a soulmate is. 

2. “10 Things I Hate About You”

“10 Things I Hate About You” proves the timeless charm of modernizing the classic romances of the past. The 1999 film — an adaptation of Shakespeare’s “The Taming of the Shrew” — maintains the intricacies of the source material while also getting the most out of its high school setting. Julia Stiles, Heath Ledger, and Joseph Gordon-Levitt are phenomenal. 

3. “Clueless”

Chic, iconic, and forever quotable, “Clueless” is a brilliant ’90s time capsule and unironically one of the most impressive Jane Austen adaptations. It’s a hilarious and unbelievably fun romantic romp through Beverly Hills that will have you yearning for Alicia Silverstone’s closet and Paul Rudd’s immortality.

4. “When Harry Met Sally”


They don’t make comedies quite like “When Harry Met Sally” anymore, and that’s primarily because they no longer make comedians quite like Meg Ryan and Billy Crystal. Their undeniable chemistry and perfect delivery anchor this romantic, decade-long, New York City epic of love and friendship. If anything, it proves that everyone needs Carrie Fisher as their best friend.

5. “Fire Island”

Not only do I feel obliged to continue this list’s trend of including modern-day adaptations of classic novels (apparently one of my favorite genres), but I simply felt compelled to end on “Fire Island” because it is a hilarious, queer rom-com featuring an ensemble of pitch-perfect performances — including one from SNL’s brightest new star, Bowen Yang — that injects new life into Jane Austen’s “Pride and Prejudice” story. 

Tyler Wilson is a staff writer for The Prospect and Humor at the ‘Prince.’ He can be reached at, or on Instagram at @tylertwilson.

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