10 Of The Creepiest Romances In Film

1. Don Jon (2013)

Joseph Gordon-Levitt directs and stars as a present-day Don Juan style womanizer named Jon Martello – and he’s addicted to pornography. After a tried and failed attempt at a one-night stand with Barbara Sugarman (Scarlett Johansson), he stalks her on Facebook and asks her out for lunch. Strangely enough, they hit it off, and a long-term relationship ensues. To Jon’s disdain, however, Barbara wants him to take night classes and watch sappy movies with her – and to top that off, they go more than a month without sex. Now, here’s the strange part: once they do have sex, Jon decides that he prefers pornography to the real deal. Barbara catches him in the act, but he dismisses the video as a dirty email chain from a friend. As Jon tries to hide his habit from Barbara, he finds himself “acting out” in more public places, a regular Casanova. Of course he gets caught again, this time by his classmate Esther (Julianne Moore). Esther begins to counsel Jon through his addiction, but not before Barbara finds out that he’s still into the virtual stuff, which puts an end to their relationship. As Esther helps Jon to kick the habit once and for all, they become intimate. As the film concludes, he declares that he isn’t in love with Esther, but he does feel an emotional connection with her – how romantic.

2. Womb (2010)

Hungary-born Benedek Fliegauf wrote and directed this cinematic jewel starring Eva Green and Matt Smith. It opens with an unnamed pregnant woman talking to her unborn child, saying that the father has left forever, but they will have a new life together. We’re then introduced to a couple of young lovers named Rebecca and Tommy. Rebecca is a computer programmer, and Tommy is a political activist. They declare eternal love. They seem like the perfect modern couple – until Tommy dies in a car accident. We then learn that the pregnant woman from the beginning of the film is Rebecca. And the unborn child? Tommy’s clone. Yes, Rebecca actually takes a sample of Tommy’s DNA, impregnates herself with the miracle of modern technology, and falls in love all over again with her quasi-lover-child. This film is all sorts of Oedipal.

3. BIG (1988)

This well-known film directed by Penny Marshall features Tom Hanks’s breakout role – a kid named Josh Baskin who wishes to be, well, not so small. To his satisfaction, the 12-year-old undergoes an overnight transformation. The next morning, he’s 30. It’s a funny concept in theory. A kid in a man’s body – there’s even a great scene in which Josh gets a job testing toys, literally every youngster’s dream job. This movie takes a turn for the weird, though, when he strikes up a romance with coworker Susan Lawrence (Elizabeth Perkins). On face value, sure, young Tom Hanks and Elizabeth Perkins are both attractive, and they make a cute couple. But remember—magic wishes aside, Tom Hanks is still a 12 year old kid! That means his fling with Susan is not so much cute, as it is illegal.

4. Meet Joe Black (1998)

Here’s a weird one. Martin Brest, the same guy who directed the zany Eddie Murphy comedy Beverly Hills Cop, also took a shot at something a little darker. Meet Joe Black stars Brad Pitt, who plays Death embodied in a handsome young man named Joe Black. Much like Big, the female love interest is named Susan—and much like Big, their relationship is creepier than it looks on the surface level. In this film, Susan (Claire Forliani) is a seriously attractive woman who has sex with the human incarnation of Death itself. Now that’s creepy. They take it even further, though. Joe Black’s human body isn’t even living, technically speaking. He claims the body of a recently deceased young man, so Susan sleeps with Death in multiple senses of the word.

5. Twilight (2008)

Most of us love to hate the Twilight series because of the flat acting and not-so-good writing. If you’re looking for another reason to steer away, though, here’s one: pedophilia. After all, Edward (Robert Pattinson) is a centuries-old vampire who just happens to make his home at a Washington-area high school instead of some gothic castle in Transylvania. From that perspective, his relationship with Bella (Kristen Stewart) takes on a decidedly creepy quality. Also, let’s be honest: Pattinson’s stone-faced vampire stare is unsettling in and of itself.

6. The Time Traveler’s Wife (2009)

As long as we’re discussing films with inadvertent pedophilia vibes, German director Robert Schwentke headed up this film starring Eric Bana and Rachel McAdams. It’s a fatalistic romance about a man named Henry (Bana), whose involuntary ability to travel through time leads to his falling in love with a young girl named Clare (Brooklynn Proulx). In one scene, he actually time travels and shows up where young Clare is playing outside – and he’s naked for some reason. He steps out from behind some bushes and befriends Clare, which leads to her falling in love with him in the future.

7. Sleepless in Seattle (1993)

This much-beloved Nora Ephron film stars Tom Hanks and Meg Ryan. Most of us know the story: Sam Baldwin (Hanks) is a recent widower, his wife having died of cancer. Looking for a fresh start, he and his son Jonah move to Seattle, where Sam delivers a radio broadcast about how much he loved and misses his late wife – as a result he becomes a heart throb for women nationwide. One particular woman, Annie Reed (Ryan) writes him a letter asking to meet up on Valentines Day. She then impulsively boards a plane to Seattle where she stalks both Sam and his son at the beach and the airport. Before they can meet, Annie decides that her actions, from the perspective of a normal non-stalker, could be interpreted as strange, so she leaves Seattle. In an artificial turn of events, Sam’s son takes a flight to New York without his dad’s permission, so they all end up together at the Empire State Building on Valentine’s Day. Sam and Annie finally meet and live happily ever after. Really though, this film’s unbelievable ending isn’t all that bad. It does do a great job of fulfilling audience fantasies – for any one of Tom Hanks’s crazed female fans.

8. 50 First Dates (2004)

Peter Segal directs this romantic comedy starring Adam Sandler and Drew Barrymore. In tropical Hawaii, Henry Roth (Sandler) is a womanizing veterinarian who grows tired of playing female tourists and charges himself with the task of romancing an anterograde amnesiac named Lucy (Barrymore). Because Lucy can’t form any new memories, she awakes every day having forgotten everything that happened the day before – thus the movie title, 50 First Dates. They end up getting married and having a child, so Lucy wakes up every day to find herself in what amounts to an arranged marriage with a kid she doesn’t know or necessarily even want. But hey – at least they live in Hawaii, right?

9. The Notebook (2004)

This film, directed by Nick Cassavetes, is most well known for Ryan Gosling and Rachel McAdams sharing a really intense kiss in the pouring rain. Noah Calhoun (Gosling) and Allie Hamilton (McAdams) meet each other in the 1940s, a time before the cynicism of today’s society wore down our faith in the tale of the star-crossed lovers. It’s the quintessential sappy love story. Let’s stop for a moment, though, and realize just how creepy Gosling’s character is. To persuade Allie to go on date with him, Noah threatens to commit suicide. Normally that would be a turn off, or perhaps a warning sign that said person is certifiably insane. In star-crossed lover world, though, it’s the equivalent of the perfect pick-up line. Allie agrees to that first date, and the rest is set in stone, or rather The Notebook.

10. Hitch (2005)

As far as creepy romance films are concerned, Hitch is a beauty. Andy Tennant directs this comedy starring Will Smith, who plays a romance consultant named Alex “Hitch” Hitchens. What does a romance consultant do, exactly? He charges very sad men money in exchange for teaching them how to get the girl of their dreams. That premise is already fairly creepy, but it gets worse. The film portrays Hitch as the guy who is so smooth he can pick up any woman. For example, he pays to have a walkie-talkie delivered to a woman at her workplace, which he uses to ask her for a first date. It’s cute in the movie – all of her coworkers react as if it’s cute anyways. In real life, though, what could be creepier? That’s the kind of story we hear about in sexual harassment reports on the evening news.