Jake Gyllenhaal Attends Met Gala 2014 Alongside Ex-Girlfriends Kirsten Dunst, Reese Witherspoon, and Taylor Swift

Celebrity News May. 6, 2014 AT 1:40PM
Maggie and Jake Gyllenhaal at the Costume Institute Gala on May 5 Jake Gyllenhaal attended the 2014 Met Gala in NYC with sister Maggie Gyllenhaal as his date Credit: Splash News

They've got you cornered, J! Jake Gyllenhaal may have stuck by sister Maggie Gyllenhaal's side during the Metropolitan Museum of Art's Costume Institute Gala for a good reason! The Nightcrawler actor attended the biggest night in fashion alongside not one, not two, but three famous ex-girlfriends! Kirsten Dunst, Reese Witherspoon, and Taylor Swift were all in attendance on the red carpet, but it appears as though none of the women made their way to Gyllenhaal for a photo-op during the overwhelmingly star-packed evening.

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At the Met Gala, a much scruffier Jake, 33, escorted Maggie, 36, as his date. He donned a black shirt, pants, and a white blazer. Dunst, meanwhile, wore an asymmetrical black gown designed by Rodarte. Witherspoon stunned in a Mad Men-inspired rosy pink Stella McCartney ensemble (Betty Draper, anyone?) as Swift slipped into a light pink Oscar de la Renta gown.

Gyllenhaal dated Dunst for two years until their split back in 2004 in what most consider his first high-profile romance in Hollywood. At the time, the couple shared an L.A. home and a dog named Atticus.

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The pair have rarely spoken of each other since, but didn't seem to part on bad terms. Back in November 2009, the Two Faces of January actress kept the Gyllenhaal talk to a minimum in an interview with Allure. "It would be nice to see him," she said. "But we're not good friends." Dunst has been dating actor Garrett Hedlund since early 2012.

Kirsten Dunst, Reese Witherspoon, and Taylor Swift at the 2014 Met Gala in NYC on Monday, May 5
Kirsten Dunst, Reese Witherspoon, and Taylor Swift at the 2014 Met Gala in NYC on Monday, May 5
Credit: Rabbani and Solimene Photography/Getty Images; Larry Busacca/Getty Images; Dimitrios Kambouris/Getty Images

Gyllenhaal's next longterm relationship was with Witherspoon. The twosome met on set of the film Rendition and took their relationship public in March 2007. Us Weekly broke news that the pair called it quits in December 2009 after nearly three years together.

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"She felt pressured to wed again but she wasn't ready," an insider told Us of Witherspoon. "She couldn't give Jake enough and she got cold feet. Jake wanted all of her." Although a source told Us there was "no drama" between the pair, an insider said the split broke Gyllenhaal's heart.

At the time, Witherspoon was mom to only daughter Ava, now 15, and son Deacon, now 11, with ex-husband Ryan Phillippe. Since the breakup, she married CAA agent Tim Roth in March 2011; the couple welcomed son Tennessee in September 2012.

Gyllenhaal may have been heartbroken from Witherspoon, but it was the actor who did the dumping during his whirlwind two-month romance with Swift, 24. The youngest one out of his exes, Swift fell head over heels for the heartthrob back in 2011.

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"It was a 180-degree turn and so out of the blue," a source told Us of the split at the time. "Jake just told her it wasn't working out...Taylor is really upset and hurt. She doesn't know what she did for him to put a stop to it. She feels really burned by him."

The sad experience, however, inspired several songs (including the heart-wrenching "All Too Well") off her 2011 Red album. Swift admitted last November that she "heard from the guy" that most of the album was about. "He was like, 'I just listened to the album, and that was a really bittersweet experience for me,'" she recalled to New York magazine. "'It was like going through a photo album.' That was nice."

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