Film’s Most Awkward Couples

People have written infinite pages about the chemistry between movie couples like Stanley and Stella Kowalski (Marlon Brando and Kim Hunter) in A Streetcar Named Desire or Scarlett O’Hara and Rhett Butler (Clark Gable and Vivien Leigh) in Gone with the Wind. While we can’t deny the magic those iconic romances have lent to the silver screen, some of our favorite couples in film are the awkward pairings that don’t quite fit. Many of these twosomes are a complete casting mismatch, but each one has the added burden of overcoming some unfortunate and uncomfortable narrative situations. See what flawed film couples we sent a Valentine to after the break. Feel free to add your own favorites in the comments.

Annie Walker and Ted / Annie Walker and Rhodes

Facing her 40s, recovering from a breakup, and mourning the loss of her business, Kristen Wiig’s Annie Walker in Bridesmaids winds up in a no-strings-attached relationship with Jon Hamm’s awesomely jerky, Ted. The first time we meet him, he can’t wait to kick Annie out of bed. “This is so awkward. I really want you to leave, but I don’t know how to say it without sounding like a dick,” he tells her. He’s a real jerkface — but Annie keeps crawling back to him, hoping the sex will lead to something more. It’s painful to watch, but things aren’t any less awkward with her new potential beau, Officer Rhodes. He does and says all the right things, but Annie isn’t receptive to his kind and loving gestures. The disastrous maid of honor and frustrated traffic cop eventually overcome their messy, uncomfortable interactions and find love, but it wouldn’t be a Judd Apatow-produced film if the matchmaking felt any less like having your teeth pulled.

Rachel Dawes and Bruce Wayne

Christopher Nolan’s The Dark Knight was the pinnacle of the awkward romance between Gotham’s District Attorney and billionaire philanthropist Bruce Wayne. We weren’t huge fans of Katie Holmes in the role for 2005′s Batman Begins, but the casting of Maggie Gyllenhaal for Nolan’s sequel was downright weird. We’re huge fans of the actress, but the duo spent most of the movie looking like unwilling partners in a game of dodgeball. With their on-screen chemistry set to low, and Gyllenhaal acting like she’d rather be in Brooklyn knitting baby cardigans for her daughter, Ramona, we felt sorry for Dawes. She never really fits the bill as an empowered heroine and succumbs to a useless, by-the-numbers treatment as Wayne’s damsel in distress. How awkward was it for Bruce, too, when his childhood friend winds up wanting to marry his nemesis (Harvey Dent/Two-Face)? We love a good noir, but this romance failed with a flop.

CW Briggs and Laura Kensington (or Woody Allen and Any Younger Actress)

We get it. These hot, young, talented women are portraying an archetype — and no one plays Woody Allen better than Woody Allen. Still, the director has a history of casting himself for increasingly ridiculous and unlikely romantic partnerships that scream awkward. Sure, that’s part of Allen’s shtick, but his career obsession with the intelligent, yet emotionally immature man and the decades younger, often naive, beautiful woman has consistently been one of cinema’s most uneasy “useful plot mechanism[s]” — even if we are capable of separating an artist’s personal life from their work.

George McFly, Marty McFly, and Lorraine Baines

“This is all wrong. I don’t know what it is. But when I kiss you, it’s like I’m kissing… my brother,” Lorraine Baines (Lea Thompson) tells Marty McFly (Michael J. Fox) — her future son — in Back to the Future. Ew. (Ok, we’re just now realizing that Lea Thompson was cast in too many creepy parts during the ‘80s.) We’re using the word “couple” loosely for this pick since Lorraine’s infatuation with Marty doesn’t lead to a real romantic relationship. Cowardly pushover George McFly — Lorraine’s future husband and Marty’s father — adds an additional layer of awkward into the mix, until he finds his courage and sets history back on the right path. The whole thing is one giant hot mess.

Jack Dawson and Rose DeWitt Bukater

Whoever says they don’t find Jack (Leonardo DiCaprio) and Rose (Kate Winslet) at least a little awkward and annoying in James Cameron’s epic, Titanic, is totally lying. We admit that things would have been a lot more uncomfortable with the twitchy, brooding Jeremy Sisto in the part of Jack. DiCaprio’s casting, however, makes Winslet look like she’s making out with her little brother for 194 minutes.

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