When it comes to the Academy Awards, it's not just about who celebrities go home with (preferably, a shiny gold dude named Oscar). It's also about who they turn up with, whether that's Mom or the pop star they've been dating on the sly.
This Sunday's ceremony is rife with celebrity couple possibilities. In a perfect world, nominees Emma Stone and Andrew Garfield will reunite and hit the red carpet together. Ryan Gosling and Eva Mendes will get a babysitter. And, while we'd never want to deny Michelle Williams a hot man-date, we'll be a little bummed if Busy Philipps isn't by her side.
Of course, strutting past Ryan Seacrest in tandem doesn't necessarily guarantee romantic longevity, as these kaput couples from Oscars past can attest. It does, however, guarantee a lifetime of fancy photos that can be both mesmerising and unbearably awkward.
Behold, 20 Oscar pairings that you're highly unlikely to ever see again.
Renée Zellweger & Jack White, 2004
The Cold Mountain costars, pictured here with Christine Taylor, were dating when Zellweger won her Best Supporting Actress Oscar. A year later, the actress eloped with a different musician: country singer Kenny Chesney.
Photo: BEI/REX/Shutterstock.
Julia Roberts & Benjamin Bratt, 2001
The actress and the Law & Order heartthrob called time on their three-year relationship just months after he watched her win an Oscar for Erin Brockovich.
Photo: PETER BROOKER/REX/Shutterstock.
Courtney Love & Amanda de Cadenet, 1995
Matching satin slip dresses, tiaras, and smudged red lipstick elevated pals Love and de Cadenet to '90s Halloween costume status following their notorious Oscars party crawl.
Photo: Dave Lewis/REX/Shutterstock.
Diane Keaton & Steve Martin, 1997
It's not clear if the Father of the Bride costars were dating or just showing up together as pals, but we've been 'shipping them ever since. Who wouldn't want to be a third wheel in this situation?
Photo: Dave Lewis/REX/Shutterstock.
Jake Gyllenhaal & Kirsten Dunst, 2003
These days, Gyllenhaal typically joins sister Maggie for red carpet events, but there was a time when he couldn't resist partying with then-girlfriend Dunst at Vanity Fair 's after-party.
Photo: RICHARD YOUNG/REX/Shutterstock.
Madonna & Michael Jackson, 1991
Before Beyoncé and Jay Z, scoring a Madonna/MJ two-fer was as good as it got. Incidentally, Madge recently confessed to making the moves on the King of Pop.
Photo: Joyce Silverstein/REX/Shutterstock.
Winona Ryder & Dave Pirner, 1995
Grunge enthusiasts will remember Pirner as the lead singer for Soul Asylum and Ryder's post-Johnny Depp boyfriend. Alas, their romance went the way of that runaway train.
Photo: D. LEWIS/REX/Shutterstock.
Owen Wilson & Sheryl Crow, 2000
That couple, that dress... so much to unpack here. Believe it or not, but Wilson and Crow dated for a couple of years before she moved on to cyclist Lance Armstrong. Armstrong would go on to briefly date another Wilson ex, actress Kate Hudson.
Photo: BEI/REX/Shutterstock.
Charlize Theron & Craig Bierko, 1997
Betcha didn't know that Charlize Theron used to date Carrie Bradshaw's jazz-obsessed love interest. Good to see he left the pork-pie hat at home.
Photo: BEI/REX/Shutterstock.
Naomi Watts & Heath Ledger, 2004
Ledger played the supportive boyfriend for Watts the year she was nominated for her work in 21 Grams. The Australian actors split in May 2004 after nearly two years of dating.
Photo: LAURA RAUCH/AP/REX/Shutterstock.
Angelina Jolie & James Haven, 2000
To be clear: Jolie and her brother were most definitely not a couple. Their affectionate nature did, however, manage to make lots of people uncomfortable.
Photo: BEI/REX/Shutterstock.
Alex Kingston & Ralph Fiennes, 1994
ER 's Dr. Elizabeth Corday and Voldemort made quite the couple back in the day. The British actors dated for 10 years before marrying in 1993 and divorcing in 1997.
Photo: BEI/REX/Shutterstock.
Matt Damon & Winona Ryder, 2000
The former couple (and double date regulars with Ben and Gwyneth) made the Oscar rounds years before Ryder really cultivated her awards show facial expressions.
Photo: BEI/REX/Shutterstock.
Sarah Jessica Parker & Robert Downey Jr., 1989
SJP and RDJ were a couple from 1984 to 1991, splitting a year before he earned his first Oscar nomination, in 1992, for Chaplin.
Photo: BEI/REX/Shutterstock.
Jennifer Aniston & John Mayer, 2009
John Mayer has seriously never looked more smug. Come to think of it, neither has Jen.
Photo: REX/Shutterstock.
Chris Robinson & Kate Hudson, 2001
A Best Supporting Actress nominee for Almost Famous, Hudson brought her then-husband, Black Crowes frontman Chris Robinson, to the 2001 ceremony. The couple split in 2006.
Photo: MICHAEL CAULFIELD/AP/REX/Shutterstock.
Brad Pitt & Juliette Lewis, 1991
Lewis, a nominee for Cape Fear, brought then-boyfriend Pitt along as arm candy on her big night.
Photo: BEI/REX/Shutterstock.
Edward Norton & Drew Barrymore, 1999
By all accounts, Norton and Barrymore kept it platonic when they joined forces for the '99 Academy Awards.
Photo: BEI/REX/Shutterstock.
Leonardo DiCaprio & Gisele Bündchen, 2005
What do you think has caused Tom Brady to lose the most sleep: Deflategate, or this picture?
Photo: E Goodenough/REX/Shutterstock.
Julia Roberts & Kiefer Sutherland, 1991
We can confirm that Sutherland was not the designated survivor for the 1991 Oscars, which he attended in support of then-fiancée Roberts, a Best Actress nominee for a little film called Pretty Woman. She would dump him three days before their wedding less than three months later.
Photo: MARK J. TERRILL/AP/REX/Shutterstock.Like what you see? How about some more R29 goodness, right here?
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