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  1. Entertainment
  2. Movies

50 Strangest Movie Relationships

Features
By Jen published 23 January 2014

Love means never having to say you're sorry... ish

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Bella and Edward - Twilight (2008)

The Strange Relationship: She's a seventeen-year-old high school student, he's a one-hundred-and-nine-year-old vampire. Do we need to say more?

Could It Ever Work In Real-Life? Seriously, he's one-hundred-and-nine years old.

He might be in the Guinness Book of World Records in real life, but he definitely wouldn't be shacked-up with a teenager.

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Ben and Sera - Leaving Las Vegas (1995)

The Strange Relationship: Alcoholic screenwriter Ben Sanderson (Nicolas Cage) heads to Las Vegas with one plan - to drink himself to death as quickly as possible.

He pays local prostitute Sera $500 to sit and talk with him for an hour, and the two end up forming a strange bond.

There are rules, of course, as Sera has to vow she will never ask Ben to quit drinking and Ben has to refrain from critising Sera's job.

Could It Ever Work In Real-Life? It's not impossible for a lonely hooker and a lost boozehound to fall in love, but with Ben's short life expectancy, we're not seeing great things from this one.

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Sam and Joon - Benny & Joon (1993)

The Strange Relationship : Definitely the sweeter end of the strange spectrum, Jeremiah S. Chechik's quirky rom-com Benny & Joon sees mentally ill Joon (Mary Stuart Masterson) finding love with oddball cinephile and Buster Keaton obsessive Sam (Johnny Depp).

Could It Ever Work In Real-Life? Absolutely. This film is often praised for its portrayal of mental illness and the stigmas that surround it, and regardless of their backgrounds, quirks and problems, Sam and Joon are quite simple an adorable couple.

Kathryn and Sebastian - Cruel Intentions (1999)

The Strange Relationship: This one just gives us the creeps.

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There's something off about step-siblings Kathryn (Sarah Michelle Gellar) and Sebastian (Ryan Phillippe) from the very first time we see them, and their oddly sexualised relationship is above and beyond the accepted level of closeness for family members.

Especially that line: "You can put it anywhere…"

Could It Ever Work In Real-Life ? It probably could, but once the dastardly couple ran out of innuendos, the conversation would be bound to dry up pretty quickly.

Leonard and Natalie - Memento (2000)

The Strange Relationship: There's nothing exceptionally strange about Natalie and Leonard's relationship in itself, but when you throw in Leonard's particular type of memory loss things definitely take a step towards the bizarre side, as Natalie uses his condition to get what she wants and protect herself.

Could It Ever Work In Real-Life? Maybe, if she'd even wanted it to.

Leonard lives in a world where he cannot trust a single person he meets (hence the obsessive tattooing and photographing), and Natalie was just another person out to take advantage, even if she did end up growing fond of him.

Victor and Emily - Corpse Bride (2005)

The Strange Relationship: Memo to self: never recite wedding vows and plant your ring on a finger-like branch.You might just find yourself accidentally married to an undead girl instead of your betrothed, like the adorably clumsy Victor (Johnny Depp).

Could It Ever Work In Real-Life? Considering Victor actually loves another girl, he and Emily (Helena Bonham Carter) actually make a pretty sweet pair. He doesn't even seem to mind all that much that she's not technically alive - maybe all that lovely blue hair acts as a pleasant distraction?

Richie and Margot - The Royal Tenenbaums (2001)

The Strange Relationship: "I think we're just gonna to have to be secretly in love with each other and leave it at that, Richie."

If it wasn't for the whole brother / sister thing, these two would be perfect.

Granted, Margot is adopted (as her father loves to remind her), but there's still something odd about dating someone who calls the same woman 'Mum' as you do.

Could It Ever Work In Real-Life? There's nothing biologically wrong with it. But it is a bit weird.

Kate and Alex - The Lake House (2006)

The Strange Relationship: Kate (Sandra Bullock) and Alex (Keanu Reeves) are loved-up pen pals separated only by, well, time.

Kate lives two years ahead of Alex, but thanks to the apparently supernatural letterbox at the lake house they both inhabit, the duo are able to converse.

Could It Ever Work In Real-Life? Let's hope not. This nauseatingly sentimental duo would get on the nerves of everyone they knew. Great 'how we met' story for dinner parties, though.

Seth and Veronica - The Fly (1986)

The Strange Relationship: Scientist Seth (Jeff Goldblum) and his journalist lover Veronica (Geena Davis) start out as your average couple, but things take a weird turn when Seth uses himself as a test subject for his new teleportation machine.

As Seth begins the nasty transformation into the Brundlefly, Ronnie actually finds herself enjoying the physical side of their relationship even more than before, thanks to Seth's new… skills.

Could It Ever Work In Real-Life? Dear God we hope not. In case you haven't seen the movie, it does not end well. We wouldn't wish that on any couple, however nauseating they are.

Henry and Lucy - 50 First Dates (2004)

The Strange Relationship: Director Peter Segal reunited The Wedding Singer power couple Drew Barrymore and Adam Sandler for this Hawaiian tale of amnesiac love.

Sandler plays Sea Life vet Henry, who's determined to date the lovely Lucy, regardless of the brain injury which has left her with Goldfish Syndrome.

Could It Ever Work In Real-Life? It could, and it has. Michelle Philpots was in a bad motorcycle accident back in 1985, and since lost the ability to retain short-term memories. Just like in the movie, her husband has to remind her of their wedding every time she wakes up.

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