Joseph Gordon Levitt and Scarlett Johansson watch movies in Don Jon The Best Unconventional Love Stories in 21st Century Movies

Love is complicated. With the benefit of rose-tinted nostalgia goggles it might be said that romance never used to be as difficult as it is today, but that’s probably not true. Since Daphne had herself turned into a tree to avoid Apollo’s unwanted advances, the game of love has been quick to fall into – and impossible to master.

Such is the case in Joseph Gordon-Levitt’s feature directorial debut Don Jon, in which Gordon-Levitt plays a porn addict who meets the one girl who he just might adore even more than the contents of his hard drive. Barbara (Scarlett Johansson) is a romantic who loves going to the theater and watching sugary-sweet love stories, so she isn’t very pleased when she finds out that Jon would rather spend his nights with the cool glow of his laptop screen than in the warm embrace of a real woman.

Don Jon isn’t the only romantic movie with a few complications to come out in recent years. Since love has been around for so long and written about so many times, it’s necessary for filmmakers to come up with new and subversive ways of framing the simple emotion of wanting to throw yourself at someone and stay with them forever. Join us on a journey through weird romance as we take a look at some of the Best Unconventional Love Stories of the 21st Century.

Matt Smith and Eva Green in Womb The Best Unconventional Love Stories in 21st Century Movies

Most of the movies on this list at least have a romance that you can root for, but Womb earns a place mainly for scoring massive points on the “unconventional” front. This one definitely isn’t for the faint of heart, and the synopsis alone is a little difficult to stomach.

Rebecca (Eva Green) and Thomas (Matt Smith) are two childhood sweethearts who only get to spend a scant few weeks together before Rebecca moves away to Japan with her family. Years later they are reunited as adults, but a few days after Thomas is killed by a truck. Unable to accept the loss, Rebecca has Thomas cloned, becomes pregnant with the clone, then poses as his mother while she raises the boy to adulthood and waits to pick things up where they left off.

Though disturbing and uncomfortable to watch, and panned by critics for the snail pace at which the plot crawls by, Womb is a tense and powerful examination of the dangerous places that obsession can take a person to, and deals unflinchingly with the moral issues surrounding cloning and incest.

Ashton Kutcher and Natalie Portman in No Strings Attached The Best Unconventional Love Stories in 21st Century Movies

No Strings Attached and its movie twin Friends With Benefits came out around the same time and have virtually identical synopses, but No Strings Attached is the slightly better movie. It helps that the script, which was originally titled F**k Buddies, was on the Hollywood blacklist of the best screenplays around before finally being put into development.

This is the kind of movie that really does feel like a product of its time, just as When Harry Met Sally, which in many ways is a precursor to No Strings Attached, was very distinctively a late eighties movie. Whereas When Harry Met Sally asked if men and women could just be friends without sexual attraction getting in the way, No Strings Attached examines whether or not friends can just have sex without stronger feelings getting in the way.

As with When Harry Met Sally, the answer to that question is apparently “no,” though there are probably friends with benefits out there who could disagree. It wouldn’t be a romance movie without any romance, though, so perhaps its inevitable that No Strings Attached manages to find love in the middle of a hook-up. Besides, how can you resist a guy who makes a mix CD for your period?

Shannyn Sossamon and Patrick Fugit in Wristcutters A Love Story The Best Unconventional Love Stories in 21st Century Movies

From the title onwards, this offbeat indie comedy has a bittersweet edge to it. Wristcutters: A Love Story takes place in an afterlife for people who have committed suicide, where everything is exactly the same, only slightly worse. The colors are muted, everything is either worn down or completely broken, and the residents are physically incapable of smiling.

This is where Zia (Patrick Fugit) finds himself when he cuts his wrists in a slum of depression after getting dumped by his girlfriend, Desiree (Leslie Bibb). He’s just settling into the afterlife with his new best friend Eugene (Shea Whigham) when he finds out that his ex-girlfriend killed herself shortly after he did, and embarks on a road trip to find her.

Along the way he meets a cult leader played by Will Arnett, a commune patriarch played by Tom Waits and – most significantly – he meets Mikal (Shannyn Sossamon), who killed herself by accident and is trying to get a reprieve from the people in charge. Mikal offers to help Zia find his lost love, but you can probably guess what happens during their journey.

Ryan Gosling in Lars and the Real Girl The Best Unconventional Love Stories in 21st Century Movies

Lars probably isn’t the first guy to ever become attached to a silicone sex doll, but he’s probably the only guy to form a strong emotional attachment.

A surprisingly touching film about a habitual introvert who manages to open up to his family and friends through his delusional romance with a life-sized, anatomically-correct doll called Bianca that he bought off the internet, Lars and the Real Girl is as much a story about the love between one person and their community as it is about a love story about a man and his mannequin. When Lars’ psychiatrist advises that the best thing to do is to play along with his delusion, his brother and sister-in-law let Bianca move into their house, and his friends start going out of their way to invite Bianca to parties and make her feel welcome.

Lars and the Real Girl was an early indie hit for Ryan Gosling before he found major stardom, and it’s an admirable performance. Gosling really sells this portrayal of a socially awkward but utterly devoted boyfriend, and don’t be surprised if you find yourself tearing up over Lars and Bianca by the end of this strange little romcom.

Kate Winslet and Jim Carrey in Eternal Sunshine of the Spotless Mind The Best Unconventional Love Stories in 21st Century Movies

This list includes plenty of films about people falling in love, but Eternal Sunshine of the Spotless Mind is the only one about  people trying to fall out of love. The nasty flipside of relationships so intense that it feels impossible to live without the other person is feeling like things would be better if you’d never met them at all.

Luckily for Joel (Jim Carrey) and Clementine (Kate Winslet), Lacuna Inc. offers them the opportunity to do just that: erase from their memories every single moment of their relationship, good and bad, all the way back to the moment that they first met. As he journeys further and further back into his past with Clementine, however, Joel begins to regret his decision and tries desperately to cling onto his last few memories of her.

Although most of it takes place in a single night, Eternal Sunshine of the Spotless Mind spans two years of a relationship, including all the bumps along the road and the truly unhappy parts that usually get hidden by a curtain fall and a proclamation of, “And they lived happily ever after.”

Angela Bettis and Anna Faris in May The Best Unconventional Love Stories in 21st Century Movies

The feeling of unrequited love is one that’s old as love itself, and the suffering of it is captured beautifully and painfully in Lucky McKee’s May, a love story wrapped up in a horror movie. Angela Bettis plays a socially awkward veterinarian’s assistant whose love life has been stunted by her chronic shyness and her lazy eye.

When she’s not sewing dogs’ legs back on, May loves to look at all the different beautiful parts that humans are made of. One day she develops an infatuation with the hands of mechanic Adam (Jeremy Sisto) and eventually gives herself a makeover and screws up the courage to finally talk to him. It seems like the perfect romance; Adam says he’s into weird stuff, which must mean he’s into May, right?

The fact that May is in a horror movie probably gives away the fact that May’s path to finding her one true love isn’t entirely smooth. While desperately trying to win Adam’s love, May also has to deal with the advances of her co-worker Polly (Anna Faris), who is a little brash and insensitive but has a beautiful neck… and a girlfriend with beautiful legs. Luckily it all comes together in the end.

Robert Downey Jr and Nicole Kidman in Fur An Imaginary Portrait of Diane Arbus The Best Unconventional Love Stories in 21st Century Movies

Love comes in all shapes and sizes, and sometimes it comes with a very thick pelt. Fur is a fictional film about real photographer Diane Arbus, who is played by Nicole Kidman, and imagines one possible way that she might have been drawn into her career of photographing people who are usually considered to be deviant, ugly or freakish.

In the film, Diane is the dissatisfied wife of a fashion photographer whose involvement in the creative process is mainly relegated to changing bulbs and film for her husband. In a world where traditional, picture-perfect beauty is revered, Diane has an urge to seek out the beauty in things that the rest of society finds repulsive.

The trigger for her own independent career is the man living upstairs. Lionel (Robert Downey Jr.) is a circus performer turned wigmaker with hypertrichosis, a condition that has left him with thick hair all over his face and body. Diane and Lionel embark upon an intense love affair and, to the chagrin of Diane’s family, Lionel introduces her to other people like him so that she might be inspired to photograph them. Fur is worth watching for the two lead performances alone; only Robert Downey Jr. can manage to look this cool despite being completely covered with hair.

Ewan McGregor and Jim Carrey in I Love You Phillip Morris The Best Unconventional Love Stories in 21st Century Movies

When trying to find interesting new places in which to meet your one true love, getting locked up in prison for fraud should probably be considered a last resort. Nonetheless, this is how Steven Russell (Jim Carrey) and Phillip Morris (Ewan McGregor) find one another in this romantic comedy based on the autobiography of real life conman Steve McVicker.

I Love You, Phillip Morris is pretty much a love-at-first-sight movie. Conflict starts to arise, however, when Steven’s unscrupulousness gets mixed up with his doe-eyed passion for Phillip, and he expresses his affection through a continued parade of illegal and immoral acts. After being released, he poses as Phillip’s lawyer and springs him from jail, whereupon he keeps them both living an extravagant lifestyle by conning his way into a high-paying job.

The chemistry between Carrey and McGregor is what sells this movie to hopeless romantics, but Steven and Phillip’s relationship is not without troubles thanks to Steven’s inability to abstain from criminally fraudulent behaviour. It’s not everyday that you find a love story in which the most difficult barrier to overcome is a chain link fence.

James Spader and Maggie Gyllenhaal in Secretary The Best Unconventional Love Stories in 21st Century Movies

We’ll soon be getting a big dose of sexy BDSM action in Fifty Shades of Grey, the movie based on E.L. James erotic novel/Twilight fan fiction. If the prospect of spending two hours with Anastasia Steele and her “inner goddess” turns you off, however, then Steven Shainberg’s 2002 film Secretary is probably the sweetest film about spanking ever made.

Secretary is both a more accurate and more complex portrayal of a BDSM relationship than James’ novel. It bucks the assumption that the submissive partner is always the weakest by showing lawyer Mr. E. Edward Grey (James Spader) emotionally buckling and losing control under the pressure of young secretary Lee Holloway’s (Maggie Gyllenhaal) seductive willingness to submit, even as Lee gradually gains more confidence and becomes self-actualized through her sexual discovery.

It’s not all about sex, though. What makes Secretary work is that, at its heart, it’s a love story just like any other, about two people who are crazy about each other and struggling to find the right way to show it.

WALL E watches a movie The Best Unconventional Love Stories in 21st Century Movies

Who needs dialogue when you have true love? WALL-E is a classic old-fashioned love story in every sense – except for the fact that the love is between two robots and a lot of it takes place in space.

WALL-E rises to the top as one of the best movies that Pixar has ever made, and it’s largely because its garbage-collecting protagonist is irrepressibly likable, from his penchant for hoarding odds and ends that he finds in the mountains of trash left behind on a barren Earth, to his friendship with an inquisitive cockroach and his brave attempts to screw up the courage to hold EVE’s hand.

Even the most severe of cynics would struggle to resist the appeal of this impossibly sweet futuristic love story about overcoming loneliness and finding the person you’ve been waiting for – especially if you’ve been waiting 700 years.

Scarlett Johansson and Joseph Gordon Levitt kiss in Don Jon The Best Unconventional Love Stories in 21st Century Movies

We hope all our readers are feeling very romantic after reading this list. Next time you settle in for a movie night with your significant other (even if you’re single and your significant other is a tub of ice cream), why not put that DVD of The Notebook away and take a walk off the beaten track into some of the more unusual movies about love, romance, excessive body hair, BDSM, cloning, space flight, prison, the afterlife, silicone sex dolls and… well, you get the idea.

If you think that your favorite unconventional movie love story deserved a place on our list, then let us know what it is and why you like it so much in the comments.

Also, read our review of Don Jon to find out if Joseph Gordon-Levitt managed to deliver a touching modern love story of his own.