Jake Gyllenhaal Dating History: Love Life, Girl Friend

This Hollywood hunk has stolen the hearts of millions with his good looks and strong personality, not to mention receiving the attention of many actresses, musicians, and models with whom the actor has been in relationships with over the years.

Jake Gyllenhaal’s dating history is filled with big names from the industry, which include Reese and Witherspoon, Kirsten Dunst, and many more. The actor was quite a player when it came to the dating game, as he was involved with several women, according to the media and various interviews.

But recently, we have come to know that  Gyllenhaal prefers to keep his love life out of the limelight. Nonetheless, since 2018 the actor has been involved with the French model Jeanne Cadieu, marking the longest relationship he has been in so far. Keep on reading to find out who Jake dated, why they broke up, and what he has been up to in recent times.

Let’s take a quick look at the names of the celebrities that have dated  Jake Gyllenhaal in the past.

NamesYears Together
Jenny Lewis2001
Kirsten Dunst2002 – 2004
Natalie Portman2006
Reese Witherspoon2007 – 2009
Taylor Swift2010
Alyssa Miller2013
Jeanne Cadieu2018-Present

1. Jenny Lewis

Jenny Lewis 

According to Jake Gyllenhaal’s dating history, he dated Jenny Lewis, the musician, and actress in 2001, who had just started her career back then. Although it was a short relationship, the two managed to build a good friendship amongst them after splitting up within a few months.

In 2011 Jake Gyllenhaal decided to pair up with Jenny to go to the Golden Globe Awards, which led to suspicions that the two may be dating yet again after all these years. But the duo was so cautious that they did not even pose together on the red carpet for a quick photograph, just in case people got the wrong idea. Whatever happened has been buried in the past, leaving Jake and Jenny to be very good friends till now.

2. Kirsten Dunst

Kirsten Dunst 

These two looked like the perfect couple when they started dating in 2002 after Jake’s sister introduced him to Kirsten. As we all know, the relationship of the young couple who were only in their 20s was very much talked about, especially when they made the big decision to move in together. Not only did they start living together, but they also adopted a German Shepherd and gave him the name Atticus.

But all that glitters is not gold, the reason being the couple shattered all their fans and announced their breakup in 2004 after being together for two years. In an interview, Kirsten said that they broke up due to the difference in their lifestyles. Jake preferred to stay at home, whereas Dunst liked to spend more time outside.

Although many couples remain friends even after breaking up, recently, we have got to know that these two are not on good terms as Kirsten said in an interview.

3. Natalie Portman

Natalie Portman 

In 2006 Jake Gyllenhaal and Natalie Portman only dated for a few months, making them the cutest Hollywood couple at that time. After their breakup, the two remained good friends and were cast together in the movie ‘Brothers’ in 2009.

Being former lovers hasn’t affected their friendship till now, as they still roast each other at any given chance. Jake roasted Natalie in 2011 at an award function, saying,’ She’s a vegan, which makes it frustrating when you’re picking a place to eat.’

4. Reese Witherspoon

Reese Witherspoon 

The two met each for the first time in 2006 on the sets of ‘Rendition.’ At first, Reese and Jake were just friends as she was married to actor Ryan Phillipe, whom she later divorced in 2007.

Soon after the divorce, Reese told the press that she had just gotten out of a marriage and wanted to prioritize her family rather than going into a relationship again. But nothing can miss the eyes of the paparazzi who caught the duo spending quality time in Rome just a month after the divorce proceedings were finalized.

In 2008 Reese Witherspoon talked broadly about her relationship with Jake, saying that they often spent weekends at her farmhouse in Los Angeles, where he liked to cook for her. She also mentioned that Jake got along very well with the two kids from her previous marriage.

Sadly, as the saying goes, ‘all good things must come to an end,’ just like this relationship did when the couple split up in 2009. Witherspoon said that Jake was looking for a long-term commitment and wanted to marry her, whereas she was not ready to go down that line so soon.

The two broke up on good terms and still spoke positively about one another. In an interview, Jake remarked that Reese is one of the strongest and smartest people he has ever come across.

5. Taylor Swift

Taylor Swift 

Another well-known name linked to Jake Gyllenhaal’s dating history is the gorgeous singer Taylor Swift. These two were first seen bonding with one another backstage on The Saturday Night Live show in October 2010.

Over the next two months, the couple was seen together very often. They spent Thanksgiving in each other’s company and also visited Nashville, where many saw the duo laughing and having a good time, making it all the more obvious that they were more than friends.

Sadly Jake was left heartbroken once again as the couple had split up just after the Christmas holidays, although neither has clarified why they have chosen different paths.

6. Alyssa Miller

Alyssa Miller 

In June 2013, Jake was seen on a romantic bike riding date with Sports Illustrated swimsuit model Alyssa Miller. Many have said that the two looked like a couple as they could not keep their hands off one another.

Once again, this relationship also took a turn for the worst when Jake had to move to LA to shoot for the movie ‘Nightcrawler’. The distance between the two was the main reason for the split up as Miller wanted a long-term relationship, whereas Jake was not on the same page as her. The couple only lasted 6 months together.

7. Jeanne Cadieu

Jeanne Cadieu 

At last, love found its way for Jake; yes, he has been with Jeanne Cadieu, the French model, since 2018, and fortunately, the couple still looks happier than ever. Although the two try to keep their relationship private, we can still shed some light on what they have been up to over the last few years.

The duo was first spotted in London and Greece together in June 2018. Later that year, they were also seen roaming around happily in Paris, comfortable in each other’s company. Although the two have a 16-year age gap, they still decided to take their relationship to the next level when Jeanne met Jake’s parents in the summer of 2019. To make things more obvious about the depth of their relationship, Jeanne went to Jake’s premier of ‘Spiderman: Far from Home’ to support him.

In 2020 Jake was interviewed and asked about his current love life saying that he wanted to have kids more than ever as it was a perfect time. From there, we realized the couple must be very serious about one another if it involves having children.

Finally, in 2021 the two made their first red carpet appearance as a couple officially when they went to see ‘The Lost Daughter’, which was shown at the New York Film Festival.

In early 2022 Jake said in an interview that the pandemic made the bond between him and Jeanne stronger as he realized that the relationship was all about love and support. Later that year, the duo was seen in Cannes, where they were attending the premier of ‘The innocent’ hand in hand.

Nonetheless, the couple is still going strong and is very much in love now.


Jake Gyllenhaal’s dating history tells us that he sure has good taste when it comes to women, as the actor has been with some of the most beautiful celebrities, which include Taylor Swift, Natalie Portman, and many others. Although the relationships did not last long, none of Jake’s exes nor Jake himself have any bitter feelings about their time together. Moreover, he has still managed to maintain good friendships with his past girlfriends and always talks well of them when asked in interviews.

However, Jake’s current relationship with Jeanne Cadieu seems to be quite serious, as he mentioned in an interview that he is even ready to get married and have children.

Let’s keep our patience and see if we can hear any wedding bells or maybe an addition to the family!

Previous articleAj McCarron’s Wife’s Net Worth, Biography, Career
Next articleWhat Is Wrong With Matt Rife Health? [Plastic Surgery And Weight Loss]
Rowshan Jahan has an exponential interest in celebrity gossip and is known for his outstanding reporting on the net worth of some of the biggest names in the industry. He covers a wide range of celebrities, including actors, musicians, athletes, and politicians, providing readers with an inside look at the lives of the rich and famous, endorsement updates, also net worth comparison.


Please enter your comment!
Please enter your name here