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18 Bad Romantic Comedies We Just Can't Help but Love

Sometimes you need to turn off your brain for a few hours

kaitlin-photo1.jpg
Kaitlin Thomas

Julia Stiles and Freddie Prinze Jr., Down to You

Miramax/HBO

If romantic comedies have taught us anything, it's that sometimes our heads say one thing and our hearts say another. That's as true in fictional relationships as it is for our relationship with the rom-coms on this list. These movies might not all be critically beloved, and not all of them have aged well, but gosh darn it, we love them! And any rom-com that makes us feel a little happiness can't be all bad, right?

In fact, the recognizable rom-com formula is actually what makes so many of these films easy to enjoy. The predictable happy ending makes us believe in true love. We want to believe, even for a little while, that there's a world in which Matthew Goode will love us too. The narrative beats might be familiar, and clichés likely abound, but the desire to fall in love and be loved in return is universal. Romance never goes out of style. 

The way these movies manipulate our emotions through contrived plots is arguably part of the point, so it doesn't really matter if the journey to get to the destination is not always well written (or well-acted or well-directed), as long as the films in question still possess the ability to make the region where our hearts should feel a little less cold and empty. Plus, sometimes, when a movie is really bad, you just can't look away.

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So, in honor of bad rom-coms everywhere, I give you a list of not-that-great movies that are actually totally great and definitely worth your love.

(Disclosure: Links to retailers may earn money to support our work.)


1. Leap Year (2010)

Watch it on: IMDb TV (free with ads), Amazon Prime Video (free via IMDb TV), Vudu (rent or purchase)
Amy Adams and Matthew Goode star in this film about a woman who travels to Ireland to propose to her longtime boyfriend on Leap Day because of a supposed tradition that says men can't deny a woman's proposal on said holiday. However, when her plans are thwarted, she meets an Irish innkeeper and falls for him instead.


2. Down to You(2000)

Watch it on: Hulu (with Cinemax add-on), Amazon Prime (rent or purchase), Vudu (rent or purchase)
There was a point in time in which every teen was in love with Freddie Prinze Jr., and that was right around the time he starred alongside Julia Stiles in this film about two college students who meet and fall in love a bit too early. In addition to also starring Henry Winkler, Ashton Kutcher, Rosario Dawson, and Selma Blair, the film also taught all of us why you should never drink shampoo.


3. Drive Me Crazy(1999)

Watch it on: StarzHulu (with Starz add-on), Amazon Prime (rent or purchase; with Starz add-on), Vudu (rent or purchase)
Before he became Entourage's resident movie star Vincent Chase, Adrian Grenier starred in Drive Me Crazy opposite Melissa Joan Hart as two neighbors who scheme to fake date each other in order to attract the attention of the people they really want to date. I'll let you figure out what happens next.


4. You've Got Mail(1998)

Watch it on: HuluHBO MaxAmazon Prime (rent or purchase), Vudu (rent or purchase)
It's hard to deny that Tom Hanks catfished Meg Ryan in You've Got Mail, so even if it is considered a classic rom-com with a stellar supporting performance from a truly great dog, it didn't age well. Regardless, now we all know how to spell fox and recognize that supporting independent bookstores is very important!


5. Just Married(2003)

Watch it on: Amazon Prime (rent or purchase), Vudu (rent or purchase)
Ashton Kutcher and the late Brittany Murphy star in this rom-com as Tom and Sarah, a young couple from different worlds who marry quickly and discover, while on their honeymoon, that marriage needs a bit more than love to work. Although some of what passes for humor will make you cringe and the film is foolish, it will still make you wonder if we haven't really appreciated Ashton Kutcher enough.


6. Fever Pitch(2005)

Watch it on: Amazon Prime (rent or purchase), Vudu (rent or purchase)
Yes, this is a rom-com starring Jimmy Fallon, the man who wasn't able to make it through most sketches on Saturday Night Live without breaking. And yes, it's about a Red Sox fan who struggles to put his girlfriend (Drew Barrymore) above his love for baseball. Honestly, the worst thing about this movie is that it will remind you the Red Sox have won three additional World Series since it came out.


7. Chasing Liberty(2004)

Watch it on: HBO MaxAmazon Prime (rent or purchase), Vudu (rent or purchase)
It's a tale as old as time: Mandy Moore is the daughter of the president who unknowingly falls for a Secret Service agent, played by Matthew Goode, who has been assigned to protect her without her knowledge. Happens to me every single day.


8. Serendipity(2001)

Watch it on: Amazon Prime (rent or purchase), Vudu (rent or purchase), Pluto TV
Fate plays a major role in this John Cusack and Kate Beckinsale rom-com that is jump-started when both attempt to buy the same pair of gloves. After putting their respective phone numbers on a $5 bill and inside a book, the two go their separate ways with the knowledge that if they find the other's number, they're meant to be. This film would not be made in 2020 because putting your phone number out into the world is just asking for bad things to happen to you.

Never Been Kissed

Twentieth Century Fox/Disney+

9. Never Been Kissed(1999)

Watch it on: StarzHulu (with Starz Max add-on) Amazon Prime (rent or purchase; with Starz add-on), Vudu (rent or purchase)
Drew Barrymore portrays a copy editor who has never had a real relationship but falls in love with a pre-Alias Michael Vartan, who portrays a hockey-loving English teacher, when she goes undercover at the local high school. Does this make any sense? Not really! But it might make you understand the difference between nauseous and nauseated.


10. The Ugly Truth (2009)

Watch it on: Hulu (with live TV), Amazon Prime (rent or purchase), Vudu (rent or purchase)
Katherine Heigl was at the height of her fame when she starred in The Ugly Truth as Abby, a morning show producer who inevitably falls for Gerard Butler's Mike, a crass TV host who coaches her through a separate relationship until she realizes the guy only liked her for the woman he thought she was.


11. Simply Irresistible (1999)

Watch it on: Amazon Prime (rent or purchase), Vudu (rent)
This movie starring Sarah Michelle Gellar features a magic crab as a major plot point. I honestly don't think I need to say much more than this.


12. Catch and Release(2007)

Watch it on: IMDb TV (free with ads), Amazon Prime Video (free via IMDb TV), Vudu (rent or purchase)
After Jennifer Garner's fiancé dies, she takes comfort in his friends, eventually falling for his best friend, which is understandable because his best friend is played by Timothy Olyphant. We should all be so lucky.


13. Because I Said So (2007)

Watch it on: IMDb TV (free with ads), Amazon Prime Video (free via IMDb TV), Vudu (rent or purchase)
Diane Keaton plays an overbearing mother who is worried her youngest daughter, Mandy Moore's Milly, will never find true love, so she takes out an ad looking for a man to date her daughter in this problematic but sweet (and I'm not just saying that because Milly is a baker) rom-com that also stars Tom Everett Scott and Gabriel Macht.


14. Penelope(2007)

Watch it on: IMDb TV (free with ads), Amazon Prime Video (free via IMDb TV), Vudu (rent or purchase), Tubi
Disclosure: Penelope is not nearly as bad as most of the films on this list, and it gets away with a lot because it's a cute fairy tale. In it, Christina Ricci plays Penelope, a young woman cursed with a pig snout, a storyline that reminds us beauty is only skin deep, in the eye of the beholder, etc. Meanwhile, James McAvoy is so charming it's honestly not fair to the rest of the world.


15. Wimbledon (2004)

Watch it on: Peacock, Amazon Prime (rent or purchase), Vudu (rent or purchase)
Kirsten Dunst stars as an up-and-coming tennis pro who falls for a veteran player (Paul Bettany) who can't keep up anymore in this rom-com that will make you want to finally figure out tennis's confusing scoring system.


16. Win a Date With Tad Hamilton!(2004)

Watch it on: HBO MaxHulu (with HBO Max add-on), Amazon Prime (rent or purchase), Vudu (rent or purchase)
Kate Bosworth portrays a woman who wins a date with a hot movie star trying to rehab his image (Josh Duhamel) in this West Virginia-set rom-com. However, she doesn't realize the love of her life, her best friend Pete (Topher Grace), has been there the whole time. Honestly, we all overlooked Topher Grace as a romantic leading man, and we should be ashamed.


17. A Cinderella Story (2004)

Watch it on: Amazon Prime (rent or purchase), Vudu (rent or purchase)
Everyone knows the story of Cinderella, but the one to watch is this Hilary Duff/Chad Michael Murray film, which updates the story (for 2004, anyway) and finds Sam (Duff) and Austin (Murray) as internet pen pals. It even spawned four (4) direct-to-video sequels!


18. The Decoy Bride (2011)

Watch it on: Amazon Prime (rent or purchase)
David Tennant wears some fabulous plaid pants and attempts to play the bagpipes in this movie about everyone's favorite rom-com trope: fake marriage. Kelly Macdonald plays a woman from a tiny Scottish island who agrees to fake-marry a best-selling English author (Tennant) to throw off the paparazzi before his wedding to an American movie star. Tennant inexplicably doesn't get to use his own Scottish accent in a movie this Scottish, but it's still cute, in a paint-by-numbers kind of way.

Looking for more recommendations of what to watch next? We have a ton of them! And if you're looking for more hand-picked recommendations based on shows you love, we have those too.