30 Random Rom-Com Couples That Didn't Quite Work

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On-screen chemistry is a tricky thing. On paper, Maggie Gyllenhaal and James Spader seem like the last two people on earth you'd want to see having a steamy affair (especially after The Blacklist). And, yet, Secretary sizzled.

Meanwhile, Hollywood keeps playing spin-the-bottle with its hottest stars. Sometimes you get an Ashton and a Mila and call it a day. Sometimes you get an Ashton and Natalie, or Ashton and Katherine, and wonder what went wrong. Or, you get a leading man who was on his second wife by the time the woman playing his love interest was born. Or, a male lead (cough, Adam Sandler, cough) who always scores gorgeous, good-hearted girlfriends despite playing guys you wouldn't even want to sit next to on a plane. Or, you get Dane Cook. Yep.

Try as they might, these rom-com couples and plots just didn't work for us. We know they can't all be Tom and Meg or Ryan and Emma, but c'mon, guys.
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Diane Keaton & Keanu Reeves, Something's Gotta Give (2004)

We're all for an older woman getting her groove on, but Keaton and "Whoa" Reeves? No. Alas, she wound up with Jack Nicholson.
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Stave Carell, Juliette Binoche & Dane Cook, Dan in Real Life (2007)

In which we're supposed to believe that the queen of French cinema would date Cook, and then ditch him for his beleaguered brother.
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Reese Witherspoon & Tom Hardy, This Means War (2012)

We love Hardy, but he's not rom-com material, especially when he's dueling Chris Pine for the affections of Witherspoon. Mad Max would not be impressed.
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Jennifer Aniston & Adam Sandler, Just Go with It (2011)

So, let's get this straight. Sandler is a sleazy plastic surgeon who convinces one gorgeous woman (Brooklyn Decker) to go out with him, based on the way he bonds with another gorgeous woman (Aniston), who implausibly agrees to pretend to be his ex-wife? And they both fall for it? Ugh. This dude should be trolling for dates on Tinder, not charming women left and right.
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Robert Downey, Jr. & Cybill Shepherd, Chances Are (1989)

It's incredible that we watched this film on VHS 20 times before we realized how unlikely a couple Downey and '80s bombshell Shepherd were. He's playing her reincarnated late husband, while also flirting with her (and, ew, his) college-aged daughter.
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Katherine Heigl & Gerard Butler, The Ugly Truth (2009)

Rom-com queen Heigl couldn't save this story about an uptight producer who falls for a crude, boorish loudmouth. A victory for male chauvinists, a defeat for self-respecting women.
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Sandra Bullock & Denis Leary, Two If by Sea (1996)

Bullock channeled Marisa Tomei in this forgettable film about a girl fed up with her thieving boyfriend. Let's just say it was no While You Were Sleeping.
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Thandie Newton & Eddie Murphy, Norbit (2007)

Why oh why did this lovely British actress get dragged into this notoriously awful cinematic trainwreck?
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Jessica Alba & Dane Cook, Good Luck Chuck (2007)

Can we just all agree that Cook has no business being a rom-com lead? Especially when it involves performing sex acts on stuffed penguins?
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Mario Cantone & Willie Garson, Sex & The City 2 (2010)

This may be controversial, but while we love them individually, and even when they hate each other ("Ed Harris?!"), we find it unlikely that Anthony and Stanford would have ever gotten married. A fling, maybe, but holy matrimony? Doubtful, and feels like a throwaway plot gimmick. Hand on heart: We miss Marcus.
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Meg Ryan & Hugh Jackman, Kate & Leopold (2001)

Yes, time-traveling gent — please help this lovelorn career girl realize she's too ambitious for her own good. By all means, whisk her off to 1876 so she can wear corsets and not vote.
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Anna Faris & Chris Evans, What's Your Number? (2011)

Not even a good-on-paper pairing like Faris and Evans could rescue this clichéd comedy. In case you've forgotten the plot, Faris slut-shames herself into not sleeping with new guys, while failing to realize she lives next to Captain America.
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Jennifer Lopez & Ralph Fiennes, Maid in Manhattan (2002)

JLo and Voldemort, together at last.
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Ellen DeGeneres & Bill Pullman, Mr. Wrong (1996)

The title says it all.
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Nick Nolte & Julia Roberts, I Love Trouble (1994)

To be fair, Nolte was named People's Sexiest Man Alive just two years before this box-office bomb came out. But casting him as a romantic lead for "America's Sweetheart" — 26 years his junior — still seems ludicrous.
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Jennifer Garner & Ashton Kutcher, Valentine's Day (2010)

Despite playing a couple in Dude, Where's My Car?, these two made a random match the second time around. It could be because we're supposed to believe that only hours after his proposal is rejected and she finds out she's dating a married man, they conveniently fall in love with each other.
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Andie MacDowell & Gérard Depardieu, Green Card (1990)

It's a sweet film, but it would take a hell of a lot more than a tricked-out apartment to make us marry Depardieu.
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Anne Heche & Harrison Ford, Six Days Seven Nights (1998)

A bickering twosome in a dangerous watery situation may have worked for Hepburn and Bogart in The African Queen, but not for this stinker. Oh, and there's a 27-year age gap.
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Sarah Jessica Parker & Matthew McConaughey, Failure to Launch (2006)

You could cast Tom Hanks and Meg Ryan in this film, and the terrible plot would still sink it. Parker and McConaughey should have stuck with that Sex and the City L.A. cameo.
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Gwyneth Paltrow & Jack Black, Shallow Hal (2001)

The Hollywood brain trust really worked overtime on this one.
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Matthew Perry & Salma Hayek, Fools Rush In (1997)

We've said it before, and we'll say it again: Could this rom-com set-up be any more improbable?
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Taylor Schilling & Zac Efron, The Lucky One (2012)

Sorry, we're just not buying Piper with anyone but Alex (or possibly Stella).
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Fran Drescher & Timothy Dalton, The Beautician and the Beast (1997)

So bad it's almost good, but Drescher really should have stuck with Mr. Sheffield.
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Kevin Costner & Jennifer Aniston, Rumor Has It (2005)

Did it really not bother anyone that Aniston's character isn't entirely sure if Costner is her dad or not? Really?
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Ben Stiller, Jenna Elfman, & Edward Norton, Keeping the Faith (2000)

The most never-gonna-happen love-triangle of all time, and that's before you throw in the fact that the guys involved are a rabbi and a priest.
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Adam Sandler & Kevin James, I Now Pronounce You Chuck & Larry (2007)

Honorable mention goes to Jessica Biel as Sandler's "real" love interest.
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Adrian Grenier & Melissa Joan Hart, Drive Me Crazy (1999)

Vincent Chase and Clarissa/Sabrina? Who cast this thing?
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John Malkovich & Ann Magnuson, Making Mr. Right (1987)

Is it okay to secretly love this movie, while still being creeped out by Malkovich as a romantic lead?
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Kate Hudson & Matt Dillon, You, Me & Dupree (2006)

We blame Hudson's romance with co-star Owen Wilson for hogging all the on-screen chemistry.
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Justin Guarini & Kelly Clarkson, From Justin to Kelly (2003)

Just... no.
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