Angelina Jolie, Matt Damon and Jake Gyllenhaal have a tendency to mix it up as far as dates go at the Golden Globes. With the 70th annual ceremony almost upon us, we're looking back at these celebs and their various plus-ones as they arrived to the star-studded event over the years.
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Jolie has had the privilege of walking the Golden Globes red carpet multiple times in her career, often on the arm of a different gorgeous gentleman. The beauty's very first adult appearance was in 1999, with then-hubby Johnny Lee Miller. Just three years later, Jolie walked the carpet with new husband Billy Bob Thorton. In 2009, the actress debuted her latest beau, Brad Pitt.
Damon is now happily married to wife Luciana Barroso, but back in 2000 the Good Will Hunting star proudly held the hand of then-girlfriend Winona Ryder. A decade or so prior, his date arrived with her Square One co-star Rob Lowe.
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Gyllenhaal has dated two award show beauties, Kristen Dunst and Reese Witherspoon. In 2003, the actor escorted Dunst to the ceremony and just three years later, Gyllenhaal would bring Witherspoon as his plus-one.
Click the video for more, and tune in to the Golden Globes on January 13 at 8 ET/5 PT on NBC.