Jake Gyllenhaal and Natalie Portman once dated back in 2006. Five years later, both of them said some interesting things about each other.
While the Star Wars alum complimented her ex-boyfriend, the Brokeback Mountain star made a not-so-flattering remark about his ex’s pregnancy.
At that time, Portman was expecting baby no. 1 with her now ex-husband, Benjamin Millepied.
Over a decade later, the Black Swan actress – who felt sexualized as a child star – discussed trying to keep her kids from working in Hollywood.
Gyllenhaal made his comments while presenting Portman with the Desert Palm Achievement Award at the 2011 Palm Springs International Film Festival. Although they were jokes, some fans began to question what really happened between them.
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Jake Gyllenhaal began acting as a child in the ’90s, but it wasn’t until the 2001 sci-fi flick ‘Donnie Darko’ that he had his Hollywood breakthrough.
Jake Gyllenhaal Said Natalie Portman’s First Kid With Benjamin Millepied Would “Need Therapy”
Before giving Portman her award in January 2011, Gyllenhaal complimented the actress during his speech. “Natalie is the Audrey Hepburn of our generation,” he declared. “She is elegant, graceful, has amazing eyebrows … is talented, really short, funny, smart, dedicated, incredibly kind.” He also brought up some “flaws” like her being “a vegan, which makes it really frustrating when you’re picking a place to eat.”
Gyllenhaal continued: “[Portman’s] also recently announced that she’s going to be a mom, and her child will probably need therapy after seeing Black Swan .”
Weeks later during the Screen Actors Guild Awards, Portman reacted to Gyllenhaal’s jokes. The Jackie actress called the Stronger star “the Cary Grant of our generation.” She said: “Well, he’s the Cary Grant of our generation. He’s so charismatic, and so dapper and smart. He’s wonderful.”
Natalie Portman and Benjamin Millepied welcomed their firstborn, Aleph, on June 14, 2011.
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Jake Gyllenhaal Dated Natalie Portman In 2006 Years After They Were First Linked
Gyllenhaal and Portman were first linked in 2002. He was 22 and she was 21. On how they met, the Road House star said during the 2011 Palm Springs International Film Festival: “I first met Natalie at a Star Wars convention waiting in line for her to sign my Queen Amadala doll and I’m really hoping she wins the Oscar, because if she does, then that doll is going to be worth a s***oad of money!”
The pair made headlines again when they were spotted on a date in New York City in 2006. Three years later, they worked together on the psychological war drama, Brothers. During a press conference for the film, Portman said of working with her ex: “This was the first time where I actually worked with actors that I knew before. “I met Tobey when I was 14.”
“I met Jake when I was 18. There was a level of familiarity from the first day, which was really a nice way to enter into it.”
The Donnie Darko actor echoed the sentiments, saying: “Because we’ve known each other, I found making the movie had some fascinating complications and interactions just as the people that we are.” Here’s a side-by-side timeline of Gyllenhaal’s and Portman’s public dating history:
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Jake Gyllenhaal’s Girlfriend Jeanne Cadieu Is 15 Years His Junior
Gyllenhaal, 43, was first linked to his 28-year-old girlfriend, Jeanne Cadieu in 2018. They were seen walking around New York City and Paris at that time. The couple is “extremely private” about their relationship, per People magazine. Speaking to Howard Stern in 2021, the October Sky alum said that the French model isn’t into “all the other stuff” that comes with fame.
“That’s part of the reason why I just adore her,” Gyllenhaal said of his girlfriend. “And not at all the main reason but, you know, one of them.” A year later, the Oscar nominee said the pandemic made him “realize” he’s “full of love” with Cadieu. He shared: “In a lot of ways, we’re family. I’m in a relationship that is full of love and support. I feel so at ease. I’m not unaware that there’s interest in my life. My life is wonderful.”
“I have a relationship that is truly wonderful, and I have a family I love so much. And this whole period of time has made me realize that.”
Gyllenhaal previously revealed to Stern that marriage is “a choice for both of” him and Cadieu. “That’s all I want is to be a good husband and a father. … That really is what I want,” he said. “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. I love her so much; she’s such a good person.”
Jake Gyllenhaal was 29 when he dated a 20-year-old Taylor Swift.
