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.
Benjamin Braddock and Mrs. Robinson (and Elaine Robinson)
It doesn’t really get more awkward than sleeping with your girlfriend’s mom. Benjamin Braddock starts his post-graduate career by embarking on a sexual relationship with the wife of his father’s law partner, Mrs. Robinson. What should be a fun way to waste his youth while figuring out the next steps in his confused life ends up becoming an affair with a depressed woman he has nothing in common with. Benjamin takes an interest in Mrs. Robinson’s daughter, Elaine, but mom’s competitive streak and creepy lies about their summer-long fling ruins his shot with her. With Elaine banished to a life of housewifery by her family, Benjamin manages to break up Elaine’s wedding in progress, and the film ends with the most awkward and uncertain moment of all. Their great escape was thrilling, but it’s clear neither knows what the hell they really want still, or that the person sitting next to them is the right partner for the journey.
Beverly Switzler and Howard the Duck
Howard is a talking alien duck. Do we really need to say more? There are only two things that make Beverly (Lea Thompson) and Howard’s (voiced by Chip Zien) bestial relationship more awkward in the 1986 cult classic: the flirting and cringe-worthy sex scene.
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.
Kelly Taylor and Justin Bell
And the Marquis de Sade Award for film cruelty goes to the people who greenlit 2003’s From Justin to Kelly. The wretched musical stars American Idol’s debut champ, Kelly Clarkson, opposite American Idol loser first runner-up (same season!), Justin Guarini, as a couple of crazy kids falling in love. The movie bombed, and Guarini’s self-esteem hasn’t been found since.
Travis Bickle and Betsy
The pairing of unhinged cabbie Travis Bickle (Robert De Niro) and Presidential campaign volunteer Betsy (Cybill Shepherd) in Martin Scorsese’s Taxi Driver is totally awkward — mostly because the relationship is inside Travis’ head. Betsy does agree to go on two dates with the stalkery driver, but Travis still hasn’t adjusted to life after Vietnam. He winds up taking Betsy to a porn theater, which pisses her off. Travis resents her disgust, but his rage isn’t wasted and helps inspire one of the coolest mohawks in cinema.
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.
Sheila Kingston and Fred Lavery
Rosie O’Donnell and Dan Aykroyd were detectives investigating a diamond smuggling operation, pretending to be a couple, in Garry Marshall’s adaptation of Anne Rice’s erotic novel (written under the name, Anne Rampling). That doesn’t make their appearance in S&M gear any less weird.
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.