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Posted Mon, February 28, 2011 2:52pm EDT

Taylor Swift, Joe Jonas & Jake Gyllenhaal, Jessica Biel & Cameron Diaz — 8 MOST Awkward Oscar Encounters!

The Oscars were filled with former flames and their new lovers, making celebs like Taylor, Jake, Reese, Cameron, Madonna and many, many more feeling very awkward!

The Academy Awards bring out every big star in Hollywood and, as such, are the cause for more awkward encounters than one could ever possibly imagine. As every celeb seems to have dated another celeb at one point or another, events such as the Vanity fair Oscar party become ripe with A-listers feeling very uneasy — here are just a few!

  • Jessica Biel/Justin Timberlake/Cameron Diaz: More awkward for Jessica most likely as Justin and Cam get along so well they’re in the upcoming flick Bad Teacher together. Not something you would want to see as his current squeeze!
  • Reese Witherspoon/Jake Gyllenhaal: The former flames both mingled with others at the shindig, Reese most likely with fiance Jim Toth by her side.
  • Jake Gyllenhaal/Taylor Swift: The newly split couple both showed up at VF but seemed to stay away from one another — or the cameras at the very least.
  • Taylor Swift/Joe Jonas: The two singers were also at VF, maybe Joe got to tell Taylor what he thought of her song!
  • Taylor Swift/Lily Collins: Taylor Lautner‘s current squeeze Lily cannot be super thrilled that her man’s ex likes to sing about her love for him.
  • Reese Witherspoon/Abbie Cornish/Amanda Seyfried: A trio of Ryan Phillippe beauties roamed the Sunset Towers, hopefully none fought over the actor — who luckily was absent!
  • Madonna/Cameron Diaz: A-Rod’s former lady love and his new woman were not seen together and oddly enough, Cam spent the whole night by Gwyneth Paltrow’s side — Madonna’s BFF!
  • Scarlett Johansson/Sandra Bullock: Come on, you never know.