Have a Funny Valentine’s Day with These Quirky Rom Coms

You know what’s fun? Romantic comedies that spend their ubiquitous 90 minutes making fun of themselves. If you’re looking to do a cozy night in with your friends, family or SO this Valentine’s Day, and you hate romance but love that heartwarming feeling at the end of a movie where the guy gets the girl, this list of quirky rom coms is definitely for you.

1. Never Been Kissed (1999)

It is morally wrong to make a list of awkward rom coms without starting with this Drew Barrymore classic. An absolute masterpiece that will make you cry, laugh and cringe (a lot), Never Been Kissed is the tale of a 20-something wallflower journalist who goes back to her old high school for an undercover story. Trying to rewrite her past high school experience as a nobody, antics and a weird not-so-inappropriate attraction to one of her teachers ensues.

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2. But I’m a Cheerleader (1999)

This little-known but hilarious satire is a dark coming-of-age tale of a high school teen who gets sent to a conversion camp when her parents find out she’s attracted to girls. Somehow, the writers take this uber-dark setup and make it into a fun, whimsical and campy tale of a girl who’s just trying to find herself and someone to love along the way.

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3. Groundhog Day (1993)

Especially appropriate for February, in this Bill Murray rom com, a weatherman gets stuck doing the same day over and over again until he does it right. The movie is about learning the lessons of being kind in life, as Murray’s character starts out as kind of a jerk. Over the course of his wintery, repetitive purgatory, he tries to seduce a love interest by learning as much as he can about her each day until he can become a man she would want.

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4. The 40-Year-Old Virgin (2005)

Steve Carrell is the absolute king of funny yet heartwarming cringe. This super-weird rom com centers around – you guessed it – a 40-year old virgin. Trying to finally break his losing streak, he makes changes when a single mom comes into his life. Packed with laughs, awkward moments and just as many “Awww” moments, this opposite-of-a-chick-flick is a blast.

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5. Always Be My Maybe (2019)

Always Be My Maybe is an inclusive and relatable twist on the classic will-they-won’t-they story of a boy and a girl who have known each other since childhood. Children of East Asian immigrants, played by comedian Ali Wong and Randall Park, the two main characters were always “supposed” to be together, but ended up going separate ways in life. Will they come back together? Honestly, this fun little film is worth watching if just for the scene where Keanu Reeves cries over eating a steak. The rest is good, too, though!

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6.  Knocked Up (2007)

The cast of this movie is absolutely stacked with actors who thrive on situational comedy – Seth Rogan Paul Rudd, Jason Segel, and Kirsten Wiig for starters. In this movie, Seth Rogan and Katherine Heigl have a drunken and very irresponsible one-night-stand that results in a pregnancy. How they navigate the situation together might bring two total opposites together. Maybe.

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7. The Wedding Singer (1998)

Another awkward bur feel-good Drew Barrymore rom com, in this movie she plays a cater waitress opposite Adam Sandler, a wedding singer. They’re both engaged, but not to each other. After Sandler’s character is left at the altar, they both start to wonder if they should, in fact, be with each other instead. This movie is full of hilarious musical moments and set in a mid-80’s horribly-styled vibe.

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8. Forgetting Sarah Marshall (2008)

The self-claimed ultimate romantic disaster movie, this fun-filled film finds Jason Segel’s character brokenhearted when his partner, played by Kristen Bell, leaves him. Segel goes on a tropical vacation to get away from it all, only to find that his ex is staying at the same resort – with her new boyfriend. Produced by the same people as The 40-Year Old Virgin and Knocked Up, this rom com, if you can call it that, is equal parts bizarre, awkward and entertaining.

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9. They Came Together (2014)

Another movie filled with the classic cast of comedy heavy hitters, They Came Together is the story of a small shop owner trying to save her business from a corporate vulture, only to find that they have some pretty aggressive chemistry – emphasis on the aggressive. Amy Poehler, Paul Rudd, Bill Hader, Jason Mantzoukas, Ellie Kemper – literally everyone in this cast is off-beat funny and equally great at those heartwarming climactic moments every romantic comedy needs.

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10. I Want You Back (2022)

This freshly-minted rom com has a little bit of everything – fresh breakups, scheming and shenanigans, awkward humor, and the classic end-of-movie twist resolution. A VP and a receptionist are both broken up with by their SOs and encounter each other in the office stairwell sobbing. They comfort each other and vow to team up to destroy their exes’ new relationships. Will they find out it’s not really their exes they want back?

Find this movie on Prime VideoPick one of these fun, heartwarming and off-beat movies for your TV-and-Chinese-food Valentine’s Day date, or binge them all on a snowed-out weekend. One thing’s for sure; you can’t be in a bad mood while sitting back in your luxury movie furniture and watching these flicks.