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Romantic comedies often have a fine line to walk. After all, without the right casting and the right screenplay, who knows how a film about…say, the relationship between a corporate lawyer and a Los Angeles prostitute could have turned out? Yet, it did, and a quarter-century later, Pretty Woman is a modern classic.

And most romantic comedies are like that. They may be cookie-cutter, but there’s a reason that pairing up Kate Hudson and Matthew McConaughey or Drew Barrymore and Adam Sandler do, generally, work. They at least seem to fit together.

That’s not always the case, though. In these examples below, for whatever reason – be it inappropriateness, lack of chemistry, or just plain weirdness – these cinematic romantic pairings went terribly, terribly awry. So, here’s our list of those romantic movies that, deep down, just make our skin crawl.

Happy Valentine’s Day. Celebrate it by avoiding these films…or watching them if, you know, that’s your thing.

Manhattan (1979)

Woody Allen and Mariel Hemingway in MANHATTAN

Speaking of old-guy creepiness. Honestly, it’s hard for some of us not to look at all of Allen’s movies through a vaguely suspicious light now, and nothing sets off more alarms than Manhattan. Allen – truly playing against type here – is a jaded comedy writer who ends up with a strikingly young (18 in real life, 17 in the movie) Mariel Hemingway. If you can get past all the creepiness, it’s one of his standout movies. I guess.

Clueless (1995)

Paul Rudd and Alicia Silverstone in CLUELESS

How charming is Paul Rudd? Charming enough to make everyone who loves this movie gloss over the fact that Cher (Alicia Silverstone) eventually ends up in a loving relationship with her stepbrother. That’s Lifetime-movie quality right here. Between that and the presence of the increasingly insane Stacey Dash and the sadly departed Brittany Murphy, this movie has become one very weird watch.

Beautiful Girls (1996)

Timothy Hutton and Natalie Portman in BEAUTIFUL GIRLS

There’s a lot of charm to be found in Ted Demme’s breezy exploration of snowbound, listless Massachusetts thirtysomethings; it certainly approaches the age with a lot more accuracy than the meanderings of, say, Zach Braff, for example. However, you know what’s not cool, given the romantic comedy leanings of the movie? The verging-on-Lolita relationship between Willie (a 36-year-old Timothy Hutton) and his neighbor, 13-year-old Marty (Natalie Portman). You think that the Professional had hints of creepiness? Just watch this one. Bill Simmons and Girls co-star Michael Rapaport, incidentally, just explored this feature on a memorable podcast.

Maid in Manhattan (2002)

Ralph Fiennes and Jennifer Lopez in MAID IN MANHATTAN

Give some credit for casting out of the box, but the only thing less believable than Ralph Fiennes as an American politician is Jennifer Lopez as a hotel maid. Sorry. One of J-Lo’s many forgettable rom-coms. Fun fact, though: this movie was actually based on a story by John Hughes!

Rumor Has It (2005)  

Kevin Costner and Jennifer Aniston in RUMOR HAS IT

You’d think it would be kind of hard to mess up a movie with a cast that includes Jennifer Aniston, Kevin Costner, Shirley MacLaine and Mark Ruffalo. Yet, this 2005 movie is a near-legendary Hollywood disaster, thanks mostly to the creepy premise – journalist (Aniston) finds out that her grandmother (MacLaine) might have inspired the story behind the Graduate, and…then, somehow, ends up in bed with her maybe-father (Costner).

No Strings Attached (2011)

Ashton Kutcher and Natalie Portman in NO STRINGS ATTACHED

The lesser of the two “casual sex” relationship movies that popped up in 2011 – in other words, it is to Friends With Benefits as Deep Impact was to Armageddon. The main problem? Natalie Portman (talented in every other film genre) doesn’t fit comfortably into romantic comedy, and when matched up with Ashton Kutcher (whose goofy talent really only fits into romantic comedies) it’s just awkward. Friends With Benefits, starring Portman’s Black Swan hookup Mila Kunis and an always-likable Justin Timberlake, is a better example of this type of comedy done right.

The Twilight series (way too many years)

Robert Pattinson and Kristen Stewart in TWILIGHT

Hey, it’s a romance for the late-2000s crowd. You have to think that “no, I never read or watched Twilight” will be the bold-faced lie of the next generations of parents, probably right alongside “no, I never voted for Trump.” These are clunky, overwrought books that – shockingly – became clunky, overwrought, and downright dumb motion pictures.

Right at the heart of the problem are the two lead romantic partners in Edward Pattinson as the sparkly brick of a vampire Edward and Kristen Stewart as the perpetually dumbfounded-looking eventual-bloodsucker Bella Swan. There’s not even the flicker of a spark here, which makes their real-life relationship all the more confounding.

Have any other cringe-worthy romantic movies for Valentine’s Day? Add them below to the comments.

3 thoughts on “7 “Romantic” Movies That Are Actually Kinda Creepy Leave a comment

  1. 1st It is ROBERT Pattinson not Edward. 2nd what is wrong with maid in manhatten. Love the movie along with clueless and happy to say twilight. Movies are for entertainment.

  2. Was the term “increasingly insane” necessary when referring to Stacey Dash? I’m sure that was a jab at her political leanings which really have no place on a movie site.

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