While their romance was brief, Gyllenhaal remained friends with the Rilo Kiley lead singer, even bringing her as his date to the 2011 Golden Globes.
Fun fact: The couple was set up by his sister and her Mona Lisa Smile co-star, Maggie Gyllenhaal. And they were a match made in young Hollywood heaven, as she had just starred in Spider-Man while he was about to become the next big thing with The Day After Tomorrow and Brokeback Mountain.
The "it" couple of the early aughts got serious pretty fast, sharing a home in Los Angeles and adopting a puppy together during their relationship. And who can forget those photos Gyllenhaal and Dunst eating in Paris, which went viral as he seemed to hate the way she ate her salad?
Given their respective levels of fame, they were a paparazzi favorite, with Gyllenhaal telling People at the time, "Kirsten and I know what's real and what isn't. We know what happens when you are both actors."
"Kirsten and Jake remain the best of friends," Gyllenhaal's rep said after their two-year romance came to and en. "Details regarding when and why their romantic relationship stopped are not being provided, but suffice it to say it happened some time ago. They are still very close."
But, ultimately, they didn't remain close, with Dunst telling Allure in 2009, "It would be nice to see him, but we're not good friends."
While their romantic relationship only lasted a few months (they reportedly went on a few dates in 2002 as well), they remained close friends and co-starred in 2009's Brothers. He even presented her with the Desert Palm Achievement Award in 2011, joking, "She's a vegan, which makes it really frustrating when you're picking a place to eat."
He then went onto describe Portman as "the Audrey Hepburn of our generation. She's graceful, has amazing eyebrows, and is talented, really short, funny, smart, dedicated, incredibly kind and Jewish!"
After co-starring together in Rendition—though they had no scenes together during the shoot in Morocco—rumors start flying that Witherspoon had moved on from her divorce from Ryan Phillippe with Gyllenhaal. And in October 2008, she couldn't help but gush about her love to Vogue.
"He's very supportive," she said. "Suffice it to say, I'm very happy in life, and I'm very lucky to have a lot of really supportive people around me who care very much for me, and, you know, that's all you can hope for in life. I am very blessed in that way."
Gylleenhaal was often photographed with Witherspoon and her two kids, Ava and Deacon, and the pair spent quality time together away from L.A. "Jake is a great cook," Witherspoon told InStyle. "He does a lot. We spend the weekends outside L.A, in Ojai, where I have a farmhouse. We have chickens and we grow cucumbers and tomatoes. I love it."
And Gyllenhaal seemed to love spending time with Witherspoon's kids. "I've learned so much from the kids in my life, and somehow they just become the center of your life and the way you look at things," he reportedly told Grazia Australia. "Obviously I exist in my girlfriend's world and my sister's world in a different way, but it's opened my heart and I feel much more grown up and want to be grown up as a result of it."
After two years together, sources confirmed to E! News the couple had split just around Thanksgiving. The reason? Nothing juicy. "There are no other people involved," the insider revealed. "The relationship just ended. It just fizzled. But they also wanted to be careful and private about it because of Reese's kids."
Clearly, there was no bad blood between the exes, as Gyllenhaal gushed about her in a 2016 interview with Entertainment Weekly, saying, "She is, as I would say about most of the women who I'm close friends with or had relationships in my life, one of the smartest, strongest people I've ever met."
Witherspoon went on to marry Hollywood agent Jim Toth in 2011, and welcomed a son, Tennessee James, in 2013.
The then 29-year-old dominated the tabloid covers and headlines after he was first spotted with Swift, then 20, in Brooklyn, as well as attending a Saturday Night Live taping for an episode hosted by one of Swift's BFFs, Emma Stone. (One of their alleged first dates? A trip to an apple farm!)
Their relationship became a big effin' deal pretty effin' quickly, with the first photos of them together making the cover of Us Weekly. And it was later revealed that Gwyneth Paltrow may have actually set the couple up after she hosted a dinner party they both attended. (Swift was friends with Paltrow's then-husband, Chris Martin.)
"It's so weird. I wonder how people find out these things," Paltrow told USA Today in 2010. "It was a while ago, so I don't know why it would come out today."
Oh, yes, the infamous Maple Latte photos, taken on a stroll in Brooklyn on Thanksgiving Day in 2010 as she was spending the holiday with his family, including sister. The photo of the two with giant smiles on their faces and Swift's arm happily hooked around Gyllenhaal would define the entire relationship, and the beverage that would become the secret clue in the liner notes of Swift's Red album that "All Too Well" was about Gyllenhaal. (In November of this year, Swift finally dropped the original, 10-minute version of the iconic song.)
After the Maple Latte outing seen 'round the world, the couple headed to Nashville to continue their first (and only) holiday celebration together.
It wasn't much of a surprise when sources confirmed that Gyllenhaal and Swift parted ways at the end of 2010. An insider close to the former couple insisted to E! News that both parties were separately "very happy," and wouldn't dish on who ended the shortl ived-but-much-covered romance.
But it was apparently all of that attention that gave Gyllenhaal major pause. "Let's just say Jake was surprised by all the attention [he found with Taylor], and the last thing he wanted was another public, surprise breakup," a source told E! at the time. "Taylor's young, you just don't know what could have happened. He needed to contain it, before it went any further. He's just not in that relationship space right now."
Alas, while their romance didn't last, it did inspire some of Swift's best songs, including "All Too Well," which references the infamous scarf.
Though a romance was never confirmed, the End of Watch co-stars sparked rumors when they were spotted getting cozy together, leaving fans to speculate their on-screen romance had become real.
She did admit to E! News that the two had become quite comfortable with each other while filming the police drama, saying, "We were shooting [End of Watch] on tiny cameras with very little lighting and a very small crew. There was a lot of improv. It felt incredibly intimate. You're in character all the time because you're shooting all the time. So Jake and I would be holding hands and suddenly we'd be like, 'Oh, we're not filming.'"
Following his big breakup with Swift, there was a lot of attention on who they both would date next. But no one predicted Gyllenhaal would move on with an actress from the CW's 90210.
While they were spotted on a breakfast date in NYC, his rep shot down romance rumors, telling E! News they were "not dating."
Gyllenhaal and the Friday Night Lights star reportedly hooked up for a bit during the summer of 2012, going on a few dates. While nothing serious came out of their brief time together, they were rumored to be hooking up again in early 2014.
According to US Weekly, a source told the mag that "they hook up whenever they're single."
The Nightcrawler actor reportedly began dating the Victoria's Secret angel and Sports Illustrated model after meeting at a SoulCycle class in NYC. But within a few months, he was officially dating another SI model...
It was revealed Gyllenhaal was dating the Sports Illustrated model after they were spotted making out a coffee shop in New York City after reportedly meeting at the gym. (Are we sensing a theme here?)
And Miller revealed to E! News that fall that Gyllenhaal was giving her tips in the kitchen. "Jake has taught me to cook some dishes," she said, gushing that he was "so good" at cooking.
A source confirmed to E! News that the pair's romance fizzled out by the end of 2013.
"Things were really good between Jake and Alyssa right up until he had to leave for L.A. to go shoot a movie in the fall," a source told US Weekly at the time. "Then the distance just really got to them."
And his Southpaw director basically confirmed that his dedication to portraying a boxer in the gritty movie caused their split. "Literally. I think he broke up with his girlfriend because he was just in the gym every day," Antoine Fuqua told Deadline.
Gyllenhaal was caught kissing his Broadway co-star after a workout class in NYC, seemingly confirming months of rumors about the pair (going all the way back to late 2014).
But Wilson had previously laughed off the reports she was dating her Constellations co-star. "He's adorable, a really good guy," Wilson raved of Gyllenhaal to Net-a-Porter's The Edit. "We've become like brother and sister a little bit. We spend so much time together. We trust that even if we have a little [disagreement]—which is going to happen because we're in a tense environment that demands a lot from us—we'll make up and we'll be fine. I trust him implicitly.
Alas, a romance was never confirmed.
The Spider-Man: From From Home star has been dating the French model for nearly three years and were first photographed together enjoying a cozy stroll in Paris in December 2018.
This fall, they attended the 74th annual Tony Awards, but didn't pose together. Days later, however, they did make their red carpet debut as a couple at the New York Film Festival premiere of his sister's movie The Lost Daughter.
Recently, he's spoken about his desire to start a family of his own. "That's all I want is to be a good husband and a father…That really is what I want," he said on an Oct. episode of The Howard Stern Show. "And now that I have fulfilled a lot of things in my career that I feel comfortable with, I can safely say that. I don't know if I could have said that before."