Who has Jake Gyllenhaal dated? Girlfriends List, Dating History

Jacob Benjamin Gyllenhaal is an American actor, who began his career during the early ‘90s, and would perhaps be remembered best for his portrayal of Jack Twist in the film ‘Brokeback Mountain’, starring alongside the late actor Heath Ledger in his most iconic role, and for which he won a BAFTA Award and received an Oscar nomination. However, his greatest box office success happens to be his latest film ‘Spider-Man: Far From Home’, in which he played the villainous ‘Mysterio’.

Jake is by all standards a brilliant actor, and so is his older sister, whom many would also know, Maggie Gyllenhaal – the reason for their success comes from their impressive genes.

Not only is the Gyllenhaal family full of successful Hollywood professionals, but it seems that they also possess an ancestral claim to nobility. Jake’s father, Stephen, is distantly related to the Swedish Gyllenhaal noble family.

Jake’s mother, Naomi, comes from a Jewish Russian-Polish family who lived in New York, making Jake a descendant of Swedish, Polish, Russian and English ancestry.

Born on 19 December 1980 in Los Angeles, California, Jake is the youngest child and only son of the film producer and screenwriter Naomi Foner and the film director Stephen Gyllenhaal, and lived a rather privileged life as a youngster.

However, his parents ensured that both their children never abused their privileges, teaching them the principles of hard work and charity through strict discipline.

From a young age, Jake expressed both an interest and talent for acting, gaining a lot of exposure to the industry through his parents’ involvement with Hollywood.

Despite his talent, Jake was never allowed to accept a part in a film if it meant that he had to leave home for too long, but did, however, star in several films directed by his father.

Jake made his official film debut in 1991, starring as Billy Crystal’s son in the comedy ‘City Slickers’.

Following this, Jake gained an invitation to star in ‘The Mighty Ducks’; however, his parents forbade him from accepting the part.

In 1993, Jake appeared in ‘Dangerous Woman’ alongside his sister, and later again in an episode of the series ‘Homicide: Life On The Streets’.

While growing up, as a way to teach him the fruits of arduous labour, Jake had to work summer jobs to provide for himself, as a busboy, a lifeguard, and at a restaurant owned by a friend of the Gyllenhaal family.

On his thirteenth birthday, Jake performed an unconventional Bar Mitzvah at a homeless shelter. His parents felt that it would help him understand the privileges he had in life, and in some way, teach him to respect such advantages. Jake finished his high school education at Harvard-Westlake School in 1998, later attending Columbia University, where he studied Eastern Religion and Philosophy.

Two years into his degree, Gyllenhaal decided to drop out of varsity to pursue his acting career, landing a role in the film that would eventually be considered his breakthrough performance, starring in the lead of ‘October Sky’, which became a box office hit.

Unfortunately, Jake’s follow-up role was not as successful, but at least he gained the opportunity to act alongside his sister again, in ‘Donnie Darko’. While the film didn’t do so well, Jake’s performance, on the other hand, was well-received by critics, who decided at the time that Gyllenhaal was one of the actors to look out for as an upcoming star.

Certainly, they weren’t wrong, as since then, Jake has starred in numerous films, some comic and some far more serious.

By all means, the ‘Brokeback Mountain’ star is a talented actor, and while his schedule seems to keep him very busy, Jake has also managed to date some of Hollywood’s most attractive women, which includes an early romance with Kirsten Dunst, to a complicated entanglement with Taylor Swift. Not to mention the inevitable rumours concerning his love life floating about.

Jake Gyllenhaal

Young Love Never Dies

During his earlier years as a fledgeling actor, back when ‘Donnie Darko’ hit theatres and the world got its first dose of Gyllenhaal, Jake had no trouble flaunting his good looks and charm. Those days he dated Jenny Lewis, the first girl to walk the red carpet with the young actor. For those who can hardly remember Jenny, she is an American singer, songwriter and actress, best remembered for playing in the ‘90s hit ‘Brooklyn Bridge’. She also became the lead singer of the indie rock band Rilo Kiley, until their disbandment in 2014.

Despite their flourishing romance back in the day, Jenny and Jake’s relationship did not last too long, as they ended their relationship that same year, but despite the lack of detail about their break-up, it seems clear that they remained friends through the years. In 2011, shortly following Jake’s break-up with Taylor Swift, he took Jenny out as his date for the annual Golden Globes Ceremony.

The gossipers enjoyed a field day, with the tension of his recent break-up still a hot topic, spreading questions, and shock, among Swift’s adoring fans.

Regardless, Jenny and Jake acted friendly and respectable, making it unclear whether or not they were actually getting back together, despite the suggestions in the media. The only sure thing about their date was that they ended things amicably, which could yet have held hope for Gyllenhaal and Swift.

During an interview following their surprise date at the Golden Globes, both Jake and Jenny admitted that they remained friends in the years that followed their break-up. According to Jenny, she’s still one of Jake’s admirers, and he’s remained a fan of her music.

That Significant Other

Jake’s second public relationship would perhaps become the most significant of his entire romantic history, and was at least among the most talked about love affairs of the early twenty-first century. It was, of course, with no other than Kirsten Dunst.

Considering how widely publicised their relationship was back then, and even late into 2016, the details of their relationship would be impossible to hide. However, even with so much exposure, there remained certain secrets that were only revealed after the couple separated. The best known fact about their relationship might be the way Jake and Kirsten met.

At the time, Dunst’s career entered what many critics consider the height of her career, as she’d just wrapped up the filming of ‘Spiderman’ in which she of course played the role of Mary Jane. Her success starring opposite Toby McGuire earned Kirsten her initial place as an A-list celebrity.

On the other hand, Jake still searched for a significant role that would establish him firmly on the red carpet. During this time, Jake’s sister, Maggie, earned her second role since making her appearance in ‘Donnie Darko’, which happened to be alongside Kirsten in ‘Mona Lisa Smile’.

While on set, Dunst and Maggie became relatively good friends, and this obviously meant that Kirsten would eventually be introduced to Jake. From the word go, Jake and Dunst’s chemistry just mixed, and it didn’t take them long after their introduction to announce the beginning of their relationship.

Of course, this was back in 2002, and at the time celebrity relationships were among the hottest topics to write about for any gossip outlet. Jake and Kirsten quickly became the’in’ couple, and when they moved in together in Kirsten’s Los Angeles apartment, it was splashed on every front page of the media.

Sadly, the pressure from the media played a large factor in their eventual break-up, but for the couple of years they spent together, it was the sweetest relationship that had everyone talking. Kirsten admitted that she fell for Jake because of his dorkiness, and Jake admitted, even long after their separation, that Dunst may well have been the love of his life.

The couple even went so far as to adopt a puppy, a German shepherd they named Atticus,  but by late 2004, the couple had announced their split, claiming that they would remain friends despite the dissolution of their relationship, and that their separation was amicable.

However, this wasn’t to be; according to Dunst in a more recent interview, she claimed that they rarely saw each other after the break-up, and added that media pressure was not the only reason they split.

Of the two partners in the relationship, Jake seemed to be the most inclined to keep his privacy, while Dunst preferred to live it up in town.

The couple continuously argued about going out or staying in, and could hardly ever reach a compromise, which in the end placed too much strain on their relationship. However, even though he never likes talking about the relationship, Jake claimed that Dunst’s reluctance to tie the knot was the real reason the couple parted ways.

After dating for nearly two years, they ended the relationship, much to the shock of their adoring fans.

It seemed, though, that neither one ever fully recovered from the split, as neither became serious very quickly with another partner.

The couple broke-up just as Jake earned his big break, following their relationship; it seemed that they switched places on the celebrity A-list.

Though the only thing Jake kept from the relationship was their pup, Atticus, their relationship remains an iconic romance in the history of Tinseltown – sadly, Atticus passed away of old age in 2015.

Drugged Up On Love

Jake subsequently took a while to form a serious relationship once again, with only a few scattered rumours in between. His next full-term relationship was with his ‘Rendition’ co-star, Reese Witherspoon. Considered one of the most influential and beautiful women in Hollywood, at the time Reese was only recently separated from her husband, Ryan Phillippe.

Jake and Reese initially met on the set of their joint credit, and according to most reports on their relationship, it was Jake who took the initiative and introduced himself to Reese.

Their romance didn’t start with quite the bang Jake might have hoped for, since Reese was still caught in the middle of her divorce. Initially, Reese admitted that she didn’t feel ready for a relationship at the time, though Jake remained a positive influence during the troubled time she experienced, constantly showing her support throughout the divorce, which eventually paid off.

While Reese felt reluctant in the beginning, her adoration for Jake grew, and the couple started dating in 2007. At the time, Jake filmed one of his most memorable films, ‘Love and Other Drugs’, while Reese worked on a secretive project.

During that time, the media published regular pics of them together, however, the intimate details of their relationship remained private. Then in 2008 the couple announced their split, and although they never mentioned any reason, many believed that, again, Jake wanted to tie the knot.

Of course, as Reese stated, she didn’t feel ready for another such commitment, and their relationship suffered the same fate as Jake’s with Dunst.

Jake Gyllenhaal

In 2009, Reese finalised her divorce from Ryan and spent most of her time focusing her attention on being a mother to her two children, Ava and Deacon. Following his relationship with Reese, Jake moved on to date Taylor Swift, though rumours would suggest there was a relationship in between.

A Swift Fling

Although Jake and Taylor’s relationship didn’t last too long, beginning in October 2010 and ending around New Years in 2011, which some believe would be like an eternity considering Swift’s history, the news of their relationship lived far longer.

According to many, the Swift song, ‘All Too Well’ is a direct reference to her relationship with Gyllenhaal, and in 2020, following a throwback post of him back in his junior years by the ‘Spiderman: Far From Home’ villain, it became all the more evident.

In the picture, Jake wore somewhat geeky glasses, which Swift’s adoring fans, the Swifties, decided to poke fun at. Among the comments they posted, many mentioned the lyrics of Taylor’s popular song, explicitly referencing the mention of his glasses in the lyrics.

Not much is known about the details of their brief relationship, but it seems the world would never let Jake forget about the fact that he once dated the most popular country/pop singer to rise to fame in the twenty-first century. Since their separation, Jake’s remained tight-lipped about the relationship, but that seems to be usual for him, while Swift made no secret of her feelings towards the actor.

Regardless of what happened between them, it became evident that Swift took the relationship far more seriously than Jake ever did – some believe that their biggest obstacle was the age difference. At the time, Swift turned twenty-one, with Jake already closed in on his thirties. Among his biggest mistakes, as proven by Swift’s lyrics, was his neglect of considering her twenty-first birthday, which the actor never attended.

In an interview sometime later, Jake admitted that he’d fallen in love only twice in his life, and this didn’t include Swift, adding that he wasn’t ready for a serious relationship with Swift, and that, in the end, is what cost them their future together. Despite the age gap, it appeared that the break-up certainly had a negative influence on the rising pop princess.

A Number Of Possibilities

Throughout the years, Gyllenhaal became the subject of numerous speculations regarding his love life, though, despite the suggestions, many of these relationships never happened. The first rumour to be spread by the media concerned Natalie Portman back in 2006.

Although she would later star as his opposite in the 2009 drama ‘Brothers’, the rumours turned out to be nothing more than a coincidence, and although they did spend some time together, the two never officially dated.

Jake Gyllenhaal

Following Jake’s split from Reese, rumours began spreading that he possibly hooked up with the Australian model, Isabel Lucas, in early 2010. However, the speculations concerning their brief relationship never gained any confirmation from either Lucas or Gyllenhaal.

Considering his private nature, it would hardly be a surprise if Jake managed to keep that rendezvous under wraps. Later that same year, Jake hooked up with Taylor, but it turned out to be a disappointment.

According to the rumours around that time, Jake moved on with his ‘End Of Watch’ co-star, Anna Kendrick. However, no evidence ever presented itself to prove that the suggested hook-up actually happened, and the rumours quickly died down when Gyllenhaal started dating Lea Seydoux, though following their relationship, it seemed Jake only had time to spark more rumours.


Among the suggestions at the time, the most noteworthy names include Minka Kelly, Rachel McAdams, and Ruth Wilson. Yet, none of the relationships had solid evidence to confirm the supposed hook-ups.

The Girls Since

Because of his acclaimed status and his undoubted good looks and charm, Jake had no shortage of romantic interests, despite claiming that he only ever loved Witherspoon and Dunst. Sadly though, the actor never tied the knot, yet, hope still remains for the ‘Prince of Persia’ actor.

Following his separation from Swift, the only confirmed encounter he had at the time was in 2012, with the French actress Lea Seydoux, but their relationship did not progress much further than that, as things between them came to an abrupt end shortly after their hook-up.

Following this, Jake entered into a brief romance with the actress Alyssa Miller, which lasted only six months. According to most reports, the couple separated because of conflicting schedules, with Miller later saying that Jake spent more time in the gym preparing for his role in ‘Southpaw’ than with her. Eventually, the lack of quality time together cost them their relationship.

Following this, the only other reported relationship Jake had was with his current girlfriend, French model Jeanne Cadieu. However, if you were hoping for juicy details, you would be up for disappointment.

The couple has kept their affair under close wraps, rarely even making public appearances together. The only known facts about their relationship are that they started seeing each other in 2018, and have been going strong to this day. After three years together, Jake’s adoring fans are keeping their hopes up of one day seeing him tie the knot. Despite their age difference, it might even be likely that Jake has finally met the woman that would wear his wedding band.

Olivia Wilson

Olivia Wilson is currently a reporter for AffairPost based in London, United Kingdom. Prior to joining AffairPost in September 2018, she was a entertainment reporter. Olivia studied journalism at Cardiff University, graduating in 2010.

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