21 Valentine’s Day Movies That Will Make You Laugh Instead of Cry

If you’re single, chances are you’ve gotten some not-so-great messaging about Valentine’s Day. While Galentine’s Day is a nice way to reclaim the holiday, there’s still so much pressure to be coupled up — and if you’re not, to spend Valentine’s Day wishing you were. So, while we’ve all enjoyed the odd Elle Woods throwing chocolates at her TV moment, why not switch things up this V-Day? These rom-coms are love stories, yes, but they’re also designed to make you laugh — not tear your heart out, as other romantic movies can be guilty of doing (*cough* The Notebook *cough*).

Whatever you’d planned to watch for your evening of wallowing, I humbly suggest a change of plans. Swap out that sad, sappy movie for one that will have you giggling all night long — or better yet, make it a marathon and blow through two or three of these priceless gems. (Those of you in relationships: Don’t worry, you’re allowed to watch these too.)

So bring on the wine, the chocolates (heart-shaped box or no, up to you), and your coziest blanket (it’s cold out there!). No matter your Valentine’s Day status, this list is full of your favorite funny, classic rom-coms sure to brighten up any Valentine’s Day stupor.

1. How to Lose A Guy in 10 Days

Kate Hudson and Matthew McConaughey make the perfect mismatched pair in this movie about a man and a woman who make a bet that pairs them together for better or worse.

2. Bridget Jones’ Diary

Arguably Renee Zellweger’s best role ever. In a quest to improve herself, a British woman keeps a diary that documents her unexpected year of love.

3. Pretty Woman

Richard Gere and Julia Roberts make one of the most iconic film duos ever in this film about a prostitute and a businessman who unexpectedly fall in love.

4. The Proposal

A Type-A boss pushes her assistant into a marriage proposal so she won’t get deported back to Canada.

5. 10 Things I Hate About You

Oh, Heath Ledger, how I could watch thee singing on those stairs all day! This ’90s retelling of Shakespeare’s Taming of the Shrew is dripping with high school nostalgia and cheesy goodness.

6. There’s Something About Mary

A second chance at ill-fated high school love leads to a lot of laughs in this classic rom-com.

7. Knocked Up

Seth Rogan and Katherine Heigl star as a mismatched pair who, after a one-night stand, decide to commit to having their baby despite the odds.

8. The Princess Bride

My favorite movie of all time. And just in case that isn’t enough of a sell, it’s a love story to end all love stories.

9. The 40-Year-Old Virgin

Steve Carell is a 40-year-old virgin. Need I say more?

10. Never Been Kissed

I’m not Josie Grossie anymore! Or is she? Drew Barrymore stars as a woman who gets a second chance at high school.

11. Hitch

Really, I just remember this movie from the iconic scene where Will Smith’s character has an allergic reaction and his face blows up like a balloon. Classic.

12. 27 Dresses

Katherine Heigl has really just nailed the chick flick genre. This film takes the saying “always a bridesmaid, never a bride” to a whole new level. Heigl plays a woman who has been a bridesmaid in 27 weddings, and now the man she secretly loves is getting married to her younger sister.

13. Sweet Home Alabama

Reese Witherspoon stars as a fashion designer who is forced to confront her country past in order to make her divorce official.

14. 13 Going on 30

Jennifer Garner stars as a 13-year-old girl who makes a wish and winds up in her 30-year-old body.

15. Trainwreck

Amy Schumer stars as the trainwreck of this tale: a commitment-phobic career woman who meets a nice guy who challenges her to take on the world.

16. Bridesmaids

Less a love story and more a friend-love story, Bridesmaids stars Kristin Wiig as an out-of-work pastry chef whose best friend’s wedding brings out the worst.

17. When Harry Met Sally

Can a man and a woman be friends without sex getting in the way? That’s the question explored in this classic rom-com starring Meg Ryan and Billy Crystal.

18. The Wedding Singer

Adam Sandler’s hair alone is enough to make you laugh in this film, and that’s before the plot even gets started. Sandler and Drew Barrymore star as two people who are both engaged to the wrong people.

19. Long Shot

Seth Rogen and Charlize Theron aren’t your most likely couple, and that’s exactly the premise of this wacky 2019 rom-com. When brash (and poorly groomed) journalist Fred Flarsky starts following polish politician Charlotte Field’s campaign, the two form an unexpected bond.

20. Isn’t It Romantic

Obviously, we love rom-coms. But what if you woke up in a rom-com — and couldn’t get out? That’s what Natalie (Rebel Wilson) faces after getting knocked out on the subway. And while walking through life like a rom-com heroine has its perks, it also has serious drawbacks.

21. Always Be My Maybe

We have such a crush on Ali Wong, so it’s not exactly surprising that we loved her rom-com too. Written by Wong, Always Be My Maybe is about two high school sweethearts (Wong and Randall Park) who reconnect as adults, and see if their spark can hold up. Wong brings her full comedic powers to this movie, so be prepared for laugh-out-loud (and maybe laugh-so-hard-you-fall-off-the-couch) moments throughout.

Valentine's Day Movies
Image: Michael Gibson/Paramount/Kobal/Shutterstock. Design: Ashley Britton/SheKnows.

A version of this article was originally published February 2018.

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