Jake Gyllenhaal's Ghosts Of Girlfriends Past 15 Surprising Women He Dated

When it comes to relationships in Hollywood there is a lot of interest in who's romancing who, and over the years Jake Gyllenhaal has been linked to many high-profile women, making his dating life one of the more interesting stories. Let's be honest, no one's really interested in Denzel Washington or Tom Hanks' romances because they've been with their wives for decades!

Some of Gyllenhaal's breakups have ended well and his former partners have nothing but nice things to say, but then there are those that ended really badly, and one ex-girlfriend, in particular, felt she needed to send out the message about how they are never, ever, getting back together.

Yes, he's been rumored to be the subject of a scathing breakup song by Taylor Swift.

And it's not just singers Gyllenhaal has been linked to, but also a number of his co-stars, including Reese Witherspoon and Natalie Portman. Some of these relationships have been more serious than others; there have been one or two cases when he just had to glance in the same direction as an actress to be linked romantically to her. With that in mind, below are 15 surprising women that have been romantically linked to Jake Gyllenhaal over the years.

15 He And Reese Witherspoon Went From Co-Stars To Love-Interests

One of Jake Gyllenhaal's most well-known girlfriends was Reese Witherspoon and the pair got together after meeting on the set of their 2007 film, Rendition. For months after they were spotted together, they were reluctant to comment publicly on their romance, and it was only in 2008, during an interview with Vogue, that Witherspoon spoke about her boyfriend, gushing about how “supportive” he was.

They split in 2009, with reports claiming they had been driven apart by their busy schedules and that things just fizzled out.

But Gyllenhaal still has nothing but affection for his former girlfriend, and said in an interview with Entertainment Weekly, “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.”

14 A Busy Schedule Was To Blame For His Breakup With Alyssa Miller

Jake Gyllenhaal and Sports Illustrated model Alyssa Miller once made a very good looking couple. The pair were reported to have gotten together in June of 2013, and in July of 2013, they were first photographed together.

They weren't afraid to show their affections for each other in public and during the course of their relationship, they were photographed multiple times; including a New York date which saw them holding hands as they walked the streets of the city, as well as a brunch with Gyllenhaal's mom. But their relationship was short-lived, and by the end of the summer they had called it quits, as for the reason? Well, this may have had something to do with how hard Gyllenhaal was training for his role in Southpaw.

Director Antoine Fuqua told Deadline (via Daily Mail), “Literally. I think he broke up with his girlfriend because he was just in the gym every day.”

13 His Relationship With Taylor Swift Produced A Scathing Song

These two were linked for only a few months from October of 2010 to January of 2011, and while there is no confirmation of what exactly went wrong, Taylor Swift and Jake Gyllenhaal's relationship doesn't appear to have ended on good terms. At least not if Swift's music is any indication.

She never names names in her songs, but according to Teen Vogue, songs that Gyllenhaal inspired include “All Too Well,” and "We Are Never Ever Getting Back Together.”

Lyrics for the latter include, "I'm really gonna miss you picking fights / And me falling for it screaming that I'm right… ” which doesn't exactly paint the picture of relationship bliss. As for their actual relationship, this was pretty public and they spent it getting lattes, sharing Thanksgiving together, and visiting Jake's sister, Maggie.

12 He Had A Lot Of Really Nice Things To Say About Rachel McAdams

Jake Gyllenhaal and Rachel McAdams starred on Southpaw together, and it seems that their onscreen romance (they played husband and wife) may have trickled offscreen too. They were spotted out together multiple times during the summer of 2014, and their hangouts spurred relationship rumors, which were made a little more believable given that they both had a history of dating co-stars; McAdams dated Ryan Gosling, and Gyllenhaal has been linked to a number of co-stars, who are featured on this list.

Whether McAdams and Gyllenhaal were dating or not was never confirmed, but the actor did have some very nice things to say about his co-star. He told Marie Claire, "I was excited to come to work. And that's no bull****. You can feel her heart when you are acting with her. I know the audience can, too, which is why people love to watch her.”

11 Kirsten Dunst And Jake Were The "It Couple" Of The Early 2000s

Kirsten Dunst and Jake Gyllenhaal were one of the cutest couples of the early 2000s. They first got together in 2002, after being introduced by Gyllenhaal's sister, Maggie Gyllenhaal, who Dunst starred with in the film, Mona Lisa Smile. According to People, things were pretty serious between these two and they were regularly spotted on red carpet events, as well as on dates.

They even shared a Los Angeles home together and adopted a puppy, which is a pretty big step in any relationship.

But it was ultimately not meant to be and the pair went their separate ways in 2004. In 2009, Dunst was asked about her current relationship with Gyllenhaal and she told Allure, "It would be nice to see him. But we're not good friends." The fact that five years later people still wanted to know about their relationship is evidence of just how much public interest surrounded it.

10 He Wasn't Afraid To Be Affectionate With Anna Kendrick

Anna Kendrick and Jake Gyllenhaal starred together in the film, End of Watch, where they played onscreen lovers. They sparked dating rumors in 2011 when they were spotted together in California looking very cozy, with Gyllenhaal's arm around Kendrick.

The relationship rumors continued and Kenrick's comments about filming End of Watch and getting into character didn't really help. According to E! News she said, "We were shooting [End of Watch] on tiny cameras with very little lighting and a very small crew. There was a lot of improvisation. 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.'" Can you really get so caught up in the moment that you forget you're filming? Also, it seems like they had no problem “acting” like they were a couple.

9 Minka Kelly Is His Go-To Girl When They're Single, Apparently

Minka Kelly is another woman that Jake Gyllenhaal is reported to have romanced, and they are believed to have had a brief fling in 2012. But whatever happened between these two was not particularly serious, and E! News claims they went on a few dates, but nothing came of it.

Us Weekly also commented on the romance, with an insider saying, “Minka wasn't into Jake when he first pursued her,” but “decided to give Jake another chance.”

There really isn't too much to report on their relationship because if there was something between them then they did a good job at keeping it on the down-low, but interestingly, Kelly and Gyllenhaal made headlines again, two years later. In 2014 there were rumors about them getting together again, with an insider telling E! News, "they hook up whenever they're single."

8 Ruth Wilson And Jake Are Believed To Have Shared A Passionate Kiss

There have been many times when actors and actresses have fallen for their co-stars, which is not that surprising considering the amount of time that they spend together, every day, for months on end. But whether this is what happened between Jake Gyllenhaal and Ruth Wilson, after they starred in Broadway's Constellations, remains unclear. That said, they were rumors of a romance.

According to E! News, the pair had been to a morning boot camp class together in New York, and when it was finished they were spotted kissing. An onlooker said, “After the class, Jake lingered by the lobby area while he waited for her to shower and change." Later revealing, "When Ruth came out, they kissed each other goodbye before parting ways. It was more than a peck on the lips between friends. This was a kiss that said, 'We're Dating.'”

7 It Was Nothing More Than An LA Fling With Olivia Wilde

In Hollywood, there is always a lot of attention surrounding celebrities and who they spend their time with, and sometimes even if two people hang out it's going to cause relationship rumors. Jake Gyllenhaal and Olivia Wilde are said to have been linked in 2011, but whatever happened between them was short-lived.

The pair sparked romance rumors when they were spotted getting flirty in Los Angeles while enjoying a night out at West Hollywood's Chateau Marmont.

An eyewitness told People they had been “touchy-feely,” and that at one point he “had his hand on hers.” The onlooker also stated, “Olivia was very cool and wasn't fawning over Jake but seemed to like the attention he was giving her.” But at the end of the night, they appeared to go their separate ways and the romance rumors soon died down.

6 Jake May Have Found Comfort In Rachel Bilson's Arms, Briefly

Rachel Bilson and Hayden Christensen were in a relationship for ten years. They first started dating in 2007, then became engaged in 2008, and finally ended their relationship in September of 2017. However, before these two finally decided to part ways for good, there was a time in their relationship when they had a brief break. This break happened in 2010 because of the issues that distance caused them while they were living between Canada and California, and according to BroBible, it was during that break that Jake Gyllenhaal made his move.

Little is known about this encounter, but there were multiple reports claiming they were dating, and one, in particular, stands out. According to a Hollywood Scoop report (via SFGate), an insider revealed, “They're trying to keep a low profile but they're definitely dating.”

5 He And Natalie Portman Made An Adorable Pair

There is a lot of interest in the women Jake Gyllenhaal dates, and it seems he has a thing for famous people. He was rumored to have had a romance with Natalie Portman sometime between 2002 and 2006, according to Fox News. The timeline may be uncertain, but regardless of what happened in their romance, these two have remained friends.

They starred together in the 2009 film, Brothers. And in 2011, Gyllenhaal actually presented Portman with the Desert Palm Achievement Award, and he had nothing but nice things to say about her.

He described her as the Audrey Hepburn of their generation, and continued on to list some of her best qualities, which include how she's “graceful, has amazing eyebrows, and is talented, really short, funny, smart, dedicated, incredibly kind and Jewish!"

4 Jake Took Jenny Lewis As His Golden Globe Date

Jake Gyllenhaal and child actress turned indie singer, Jenny Lewis, are believed to have dated for less than a month way back in 2001, which would make his relationship with Lewis one of his first high-profile romances. Not much is known about their brief encounter, but according to Zimbio, she attended the premiere of his movie, Donnie Darko with him.

Then ten years later, the pair came back onto everyone's radar when Gyllenhaal took Lewis as his Golden Globes date to the 2011 awards. This time it was not romantic though, but rather as friends, and according to PopSugar, they have been friends for a long time. Gyllenhaal has also shown his support for Lewis' music and has been a fan for many years, even showing up to watch her play a Coachella performance.

3 French Actress Léa Seydoux May Have Wooed An American Beau

There is very little evidence pointing to a serious relationship between Jake Gyllenhaal and French actress Léa Seydoux, but in 2012, they were spotted spending time together which sparked relationship rumors. This romance is definitely not one of Gyllenhaal's most well-known relationships, and neither he nor Seydoux has commented on it, but according to Who's Dated Who, these two enjoyed each other's company, although it was only for a hot minute.

Whatever this pair shared, it wasn't meant to be (obviously, because they are no longer together), although neither of them are losing any sleep over it.

It worked out well for Seydoux and she's been in a long-term relationship with her partner André Meyer since 2015. This is also the man who she started a family with in 2017, as she became a mother to their son, George.

2 His Lunch Date With Rashida Jones Led To Questions About Their Relationship Status

Jake Gyllenhaal and Rashida Jones are believed to have met at an event in January, not long after Gyllenhaal and Taylor Swift broke up. But they came onto everyone's radar when they were spotted together on a lunch date in 2011. Jones and Gyllenhaal were seen strolling with the actor's dog, Atticus, and then, according to E! News went to Los Angeles' Café Gratitude.

Daily Mail reports that they were seen laughing and joking with each other, generally just having a good time, and that they appeared to be incredibly comfortable in each other's presence. At one point, Gyllenhaal reportedly even stole food from his lunch date's plate. But this was not so much a romantic date as it was a date among friends. Still, that did nothing to stop headlines questioning whether the two were an item.

1 Romance Rumors With Isabel Lucas Heated Up In Montreal

There are rumors that Jake Gyllenhaal and Australian beauty Isabel Lucas enjoyed a brief encounter in April of 2010. His last high-profile relationship before her would have been with Reese Witherspoon (the couple announced that they were calling time on their relationship at the end of 2009). According to Lainey Gossip, the pair were enjoying time together in Montreal, where Gyllenhaal was filming his movie, Source Code.

They were seen at Garde Manger and according to the publication, the actor was “all cuddled up” with Lucas.

The publication also reported that when Gyllenhaal was not cuddling Lucas he was apparently trying to get her to dance with him, and she seemed shy. However, in June, Lucas was asked about her relationship, to which she responded, “We're just friends! Our relationship is purely platonic.”

References: Entertainment Weekly, New York Daily News, Entertainment Weekly, Huffington Post, E! News, E! News, Who's Dated Who, Daily Mail, Teen Vogue, The Telegraph, Marie Claire, Nicki Swift, Us Magazine, People, PopSugar, E! News, E! News, Us Magazine, E! Online, Vanity Fair, People, Who's Dated Who, Harper's Bazaar, BroBible, SFGate, Us Magazine, IMDB, Who's Dated Who, Fox News, PopSugar, Zimbio, Who's Dated Who, Who's Dated Who, Huffington Post, People, Cosmopolitan, Daily Mail, JustJared, Lainey Gossip