From her songs, it seems Gyllenhaal did a number on Swift but what about other women the actor has dated? Let’s take a look at Jake’s dating history. Is it as shady as it seems or are we judging him too hard?
He Has a Problematic Pattern
We know you guys are dying to get to the dirty details, and we are dying to disclose them. But before you do, there are a couple of things you need to know about Jake and his family.
Jack was born in L.A. on December 19th, 1980. Nine years later, on December 13th, 1989 Taylor Swift was born. When the two dated, he was 29 and she was 20, which isn't the biggest age gap we've heard of, yet when you look at his exes, you can see a pattern.
He Is Hollywood Royalty
Jake grew up with money and was born to what many would describe as Hollywood Royalty. His mother, Naomi Foner, is both a film producer and screenwriter.
Stephen Gyllenhaal, his father is a film director. This might explain why both Jake and his sister Maggie turned out to be actors, as they grew up soaking film, theater, and culture in their household.
He Had a Bar-Mitzvah
Gyllenhaal is Jewish on his mother's side. She is an Ashkenazi Jew and has family in Russia and Poland. Jake definitely defines himself as Jewish and he even had a Bar-Mitzva event to celebrate his 13th birthday. His Bar-Mitzvah wasn't exactly traditional, though.
According to his parents, they wanted his 13th to mark how grateful he should be for everything he has. That's why they took him to volunteer at a homeless shelter.
Jenny Lewis
The actor must have a thing for singer-songwriters, as in 2001 when he was 21, he dated Jenny Lewis, who is known as the lead singer of indie band Rilo Kiley. She was just beginning her career, but the two were definitely a hot indie item.
Lewis is actually four years older than Jake and was 25 when they dated, we guess he has a thing for age gaps?
They Stayed Friends
Usually, when people break up they say that they'd love to remain friends, but most of the time, that's a blunt lie. It seems that Jenny and Jake took that sentence seriously...
Unlike some of his other notable exes, Lewis and Gyllenhaal remained friends. He took another girlfriend of his, one Reese Witherspoon, to see Lewis in concert. In 2011, ten years after they parted ways romantically, they even went to the Golden Globes together. Inspiring or weird? We'll let you decide...
Kirsten Dunst
Gyllenhaal dated the "Bring It On" star, Kirsten Dunst, for just a little over two years. Dating someone for two years definitely counts as a serious relationship in our book.
While they both acted in Spiderman movies, Dunst was a part of the original movies with Tobey Maguire, and Jake played Mysterio in 2019's "Spider-Man: Far from Home" with Tom Holland.
They Adopted a Dog
Kirsten and Jake dated between 2002-2004 after meeting each other, how predictable, on a movie set. Jake's sister, Maggie had a part in the movie "Mona Lisa Smile." When Jake came to visit his sister, he met Dunst. The two became inseparable, they moved in together and adopted a dog.
They named their German Shepherd "Lovey." Cute? Or is it too on the nose? We'll let you be the judge of that.
She Dumped Him
It seemed the two had a nice thing going for them, so what happened? Rumor has it that in the end, it was actually Dunst who dumped Gyllenhaal in 2004 when they were both 22.
Except for the fact they were both very young and maybe didn't want to commit, what could have compelled her to say goodbye to someone who millions of fans consider to be "The perfect man"?
Major Issues
According to Kristen, they had some major compatibility issues. While she was looking for more romance in the relationship, i.e. going on dates, Jake just wanted to stay in.
Seems like a very minor thing to break up over, if you ask us, but maybe she felt like he wasn't putting in enough of an effort? According to Swift's songs, this could definitely be the case.
Kirsten After Jake
After the two broke it off, Kirsten has continued dating. She was linked to Adam Brody and Justin Long but ended up settling down in 2017 with someone else altogether.
While he isn't as known as she is, Jesse Plemons is also an American actor. The two met on the set of "Fargo" in 2016, and have since hs two beautiful sons.
Natalie Portman
Could you imagine meeting someone while shooting a war film? We can't. Not only because we don't work in the film industry, but also because we don't find war particularly romantic, but maybe that's just us.
Jake met Natalie in 2009 on the set of "Brothers", a film that was inspired by Homer's The Odyssey. The two managed to keep whatever it is that they had pretty private, and most likely their affair was a short one.
He Gave Her an Award
Just like with Jenny Lewis, it seems that Portman and Gyllenhall remained friends. Jake even presented her with an award in 2011, calling her a modern Audrey Hepburn.
If we met a guy that compared us to Audrey Hepburn, we'd stay with him. While talking about Natalie during the ceremony, he mentioned it was hard finding a place to eat with her, because she has a plant-based diet. Could this be the reason why the two broke up?
Portman After Jake
We have noticed a pattern with Jake — it seems like many of the women he would have loved to settle down with, find the love of their lives just after splitting up with him. Ouch.
It seems like this was the case for Natalie, who met her husband Benjamin Millepied right after her romance with Jake ended. They married in 2012. The couple has two children together.
Reese Witherspoon
One thing that seems to follow Jake around wherever he goes, is his tendency to break off relationships only to then later get back together again. A prime example of this is Swift's most known song about him "We Are Never Ever getting Back Together." Such a case was his relationship with Reese Witherspoon.
Gyllenhaal met Reese on a movie set. She was in a difficult time in her life, trying to finalize her divorce from actor Ryan Phillippe. Jake and Reese spent a total of almost three years together, including some breaks in the middle.
Rachel Bilson
During one of his breaks from Reese, Jake dated Rachel Bilson, who you probably remember as Summer from "The O.C." Funnily enough, just like Reese, Rachel was also going through a challenging time.
Just before she met Jake she was engaged to Hayden Christensen, but the two broke it off for reasons unbeknownst to the public. At this time, Bilson's name has been linked to Gyllenhaal but after the two called it quits, she was back with Christensen. Ouch.
He Was Smitten With Reese
Jake had only said great things about her, praising Witherspoon as the most intelligent person he's ever met. He also added that she's extremely strong and knows how to handle herself. But, alas, after dragging the relationship for three years the "Legally Blonde" actress broke Jake's heart.
While they were both trying to claim that the relationship ended without any drama, we know better than that. There's no such thing as a breakup without drama!
He Proposed, She Refused
They don't want you to know this, but sources close to them claimed that while the two were on a romantic getaway together, Jake pulled out a ring and asked Resse to marry him. But the newly divorced actress was not ready to go down the aisle again and said no. Ouch!
Considering the fact she just got out of a marriage, we can't blame her. But, just two years later she married Jim Toth. Was it just a timing issue that broke this couple apart or was there something more?
Life After Reese
After Reese broke his heart, Jake seemed a little lost, which makes sense. For many of us, it can take a long time to recover from a serious relationship that has gone sour.
The famous actor was literally all over the place and was seen with many different actresses and Hollywood personalities including Taylor Swift, Anna Kendrick, Busy Philipps, and Rashida Jones. Busy boy.
Reese After Jake
After finally saying goodbye to Jake in December of 2009, Reese was back on the market. Even though she didn't want to settle down with Gyllenhaal in 2010 she was ready to do that with her future husband, Jim Toth.
She loved that he wasn't a celebrity and that they could lead a more private life together. When they met he was working as a talent agent. They married in 2011 and had a son together in 2012.
Isabel Lucas
First on his journey to try and get over Reese was with the Australian model and actress Isabel Lucas. It was reported that the two had a very short fling somewhere during the month of April 2010. They supposedly hung out in Montreal together but when asked about the relationship the actress said that the two were just friends.
To this day, neither Isabel nor Jake confirmed that they had something. Whether this was something they chose to hide, or we were just imagining, we'll never know.
Taylor swift
In 2010, Swift was already a pretty established country singer. She won a Grammy for her 2008 album "Fearless" and was making a name for herself in the music industry. Still, let's face it, Jake was much bigger than her.
At this point, he had already starred in iconic critically acclaimed movies such as "Donnie Darko" and "Brokeback Mountain." Still, Gwyneth Paltrow thought the two might be a good match and introduced them to each other.
How Long Did It Last?
As far as what the public knows, the Swift-Gyllenhaal romance only lasted three or four months. Fans of Swift, on the other hand, have speculated that they actually dated for at least nine months. This, according to clues they found in songs she'd written about him.
Her entire 4th studio album "Red" is dedicated to their affair. In the three months the masses were aware of their relationship, it was hard for them to get away from the Paparazzi, still, today, it's very hard to find photos of the two together.
Way Too Public
By early 2011, the publicity of their relationship was becoming hard to manage. Was that the real reason why they broke up, though? While we will never know the actual reason, we do know that it was Jake who called it off.
He claimed it just wasn't working out. But if you listen to the songs Taylor wrote about him, it seems it was a little bit more complicated than that.
Loving Him Was Red
Sources close to Swift said she was hurt. Luckily for her, that pain inspired one of her most successful albums, "Red." It was originally released in 2012 and was said to be entirely about heartbreak. The original album featured 16 songs.
In the Deluxe version, there were three new original songs as well as three demos. Songs that were speculated to be about Gyllenhaal are "State of Grace", "Red", "We Are Never Ever Getting Back Together", and of course "All Too Well."
All Too Well
The song "All Too Well" was never one of Swift's big hits but it became a fan favorite. Over the years, Swifties became more and more obsessed with this one song.
The song details the end of their relationship, Swift's heartbreak, and Jack's supposed cruelty towards Taylor. The song did not present Jack in a positive light, but at least that was a long time ago.
Swift After Red
After the heartbreak she experienced with Jake, Taylor took some time off dating. Still, her name was linked to "One Direction" singer Harry styles. Many believe that her 2014 song "Style" is about their relationship.
Later, while Jake was dating around, she settled with DJ Calvin Harris for a year. In 2016, the two broke up, which led to a public feud between the two, where they aired some dirty laundry.
Anna Kendrick
Anna Kendrick is both an actress and a musician, both of which are Jake's type. The two met on the set of "End of Watch" but the relationship didn't last long. It seems like the two were meant to be together, but at this point, Jake was not yet over Reese.
It didn't matter that he was dating a talented successful women, he was just not ready for anything serious and the two broke it off quickly.
Anna After Jake
Anna did eventually move on, this time she decided to avoid the drama and not date a fellow actor. She got together with cinematographer and director Ben Richardson in 2014.
One of his most well-known films is "The Fault in Our Stars," in which he took on the role of director of photography. The two sadly broke up in 2020 after six years of dating. We will never know what ended the relationship but we hope Anna has great things in her future.
Rashida Jones? Busy Philipps?
Gyllenhaal has a reputation for being a bit of a player, and while you should never believe everything that you read online, we think his next romance proves the point. Just a few days after Jake was seen with Kendrick, he was spotted having a romantic lunch with "Parks and Recreation" actress Rashida Jones.
If that's not enough, the day after that he was seen having dinner with "Cougar Town" actress Busy Philipps. He should just take a night off.
Olivia Munn
Is there a woman in Hollywood Jake has not been linked to? We can't think of any. Actress and host Olivia Munn was spotted chatting with Gyllenhaal at a party.
Munn was trying to get over Chris Pine, while Jake was still (yes, still!) trying to get over Witherspoon. It has been reported that Munn gave Jake her number, but he didn't really do anything about it...
Jessica Lowndes
Jessica who? We asked ourselves the same question. You might have seen her on 2008's "90210," which aired on the CW. She played Adrianna Tate-Duncan on the show and has made some appearances in Hallmark movies.
Jake and Jessica were seen out and about in NYC. Honestly, though, their connection didn't really stand a chance. Reese had just gotten married when Jake met Jessica. We think he was probably preoccupied thinking about the one that got away.
Olivia Wilde
The story goes that Olivia, who was Hollywood's it girl in 2011, wasn't that into Jake. Still, it has been reported that the two met at several different A-lister parties.
The two flirted for a while, and Wilde loved the attention. The two kept stating they were just friends, but they were seen together at a few different NYC restaurants. In the end, it seems like nothing has come of it.
Wilde After Jake
Olivia was engaged to Jason Sudeikis in 2013, and the two have two kids (a son and a daughter) together. Sadly, the two split up in November of 2020. They were engaged for seven years.
Wilde moved on pretty quickly with no other than the gorgeous Harry Styles. This gets complex, as Harry Styles dated Swift, Swift dated Jake who dated Olivia, and now she is dating Styles! Are you following?
Rachel McAdams
So, listen to this. On the one hand, we've heard whispers that the two were together for almost a year, but on the other, neither of them has ever actually confirmed such a thing. They apparently met on the set of "Southpaw," and while it seemed like sparks were flying, they kept claiming they were just friends.
We really do hope they were together. Who wouldn't want to date Rachel of "The Notebook" and "Mean Girls" fame?
More Than Just Friends...
Despite their attempts at denying there was anything between them, an interview Jake gave about her has convinced us otherwise. He has said that she's extremely dark and deep, yet she still manages to light up every room she walks into.
He added that it's uncommon to have the ability to be both gloomy and glowy at the same time, and he called the quality infectious. Have you ever said anything like that about one of your platonic friends? Yeah, neither did we.
Rachel After Jake
Whatever happened between McAdams and Gyllenhaal remains in the past. The actress has moved on to bigger and better things, both professionally and romantically. She went on to star in movies like "About Time", "Spotlight" and "Doctor Strange."
Her love life took a turn for the best when she met screenwriter Jamie Linden in 2016. The two have been together ever since.
Dakota Johnson
Yes, the daughter of Don Johnson and Melanie Griffith and the star of the "Fifty Shades" movies, Dakota Jonson dated Jake. They had a nice thing going when all of a sudden, Gyllenhaal ended the relationship unexpectedly without giving the actress an actual reason.
After the bizarre incident, Gyllenhaal tried to get her back in many different ways, including popping the question and asking her to be his wife. She wasn't impressed. Taking a page out of Taylor Swift's book, Dakota decided that she and Jake are never ever getting back together.
Dakota After Jake
Johnson has moved on and prefers to spend her time with men who are less fickle than Jake. She has been dating Coldplay lead singer Chris Martin since 2017, and the two are still going strong.
They don't share a lot about their private lives, but we bet the two know how to have fun together. Most importantly, we bet, or at least we hope, that Chris knows how to treat a woman right.
Lily Collins
"Emily In Paris" Star Lily Collins was head over heels in love with Jake. They met, how unlikely, on a movie set! The two were filming "Okja" together, and rumors of the two being more than friends started to circulate.
Collins was trying to pursue Gyllenhaal, as she was having trouble getting dates because of her fame. Dating a fellow actor seemed like the right fit. It is unclear whether Lily actually ended up making her move on Jake, but we do know that the two are not together.
Lily After Jake
Luckily for Lily, she did end up finding her happily ever after. She found it with Charlie McDowell, an American writer and director.
His most notable work is his 2014 film "The One I Love." It is unclear how the two met, but they started seeing each other in 2019. By 2020, they were engaged and in 2021 they finally tied the knot.
Emma Stone
In 2017, rumors started circling about Gyllenhaal and Stone. The actress had an amazing year, starring with Ryan Gosling in "La La Land" and being nominated for many different awards for her role as Mia.
While it has never been confirmed that the two had a thing, sources claim that they were seen together quite a lot during award season. It is unclear what went wrong, but we were really rooting for these two. They could have made a beautiful couple.
Emma After Jake
Like many of Jake's exes, Emma ended up with someone who works in the industry, but not with an actor. It seems like actors just date around too much and can't be trusted.
Emma met her husband Dave McCary, who is a writer and director, in 2017. By 2019, they were already engaged, and in 2021 they welcomed their first daughter, named Louise Jean McCary, into the world.
The Return of the Ex
Unfortunately for Jake, because of a feud with her old label, Taylor has taken on re-recording her first six albums. Knowing that "All Too Well" is a fan favorite, she released the previously unheard, unedited 10-minute version of the song. Then, she performed it on SNL.
And it didn't look good for Jake. The song, as well as a short film Swift wrote and directed, both emphasize the age difference and power imbalance between the two.
Guilty?
After Swift re-released her album "Red" in 2021, Jake went into hiding. Many Twitter users were dying to get his response, making mean memes and tagging him, but he remained quiet. Everyone, online and offline was talking about him and about how he wronged Swift.
It didn't help that a movie he shot earlier that year, titled "Guilty" hit Netflix exactly when "All Too Well" was re-released.
The Scarf Drama
Then, there's the scarf. In her song, Taylor mentions forgetting her scarf at "your sister's house." Maggie Gyllenhaal has been asked about the scarf many times and claims she has no idea what people are talking about.
When "Red" was re-released, people started campaigning for Jake to give Taylor her scarf back. Whether she got it back or not, we will never know.
Taylor After Jake
Despite rehashing all of this drama from the past, both Taylor and Jake have moved on. Taylor has been dating British actor Joe Alwyn since 2016, and the two are still going strong.
Unlike the relationship she had with Jake, Joe and Taylor keep theirs very private. There are only a handful of photos of them together in public. They both try not to talk about each other too much, and it seems like it's working for them, as this is Swift's longest relationship.
Jeanne Cadieu
Jake's most recent partner is a French model named Jeanne Cadieu. The two have quite the age difference between them, 16 years. He was born in 1980, while she, in 1996.
Considering the fact that Swift blasted him for dating younger women, this doesn't look good for him. In her new version of "All Too Well," she sang about how she'll grow old, but Jake's lovers will stay her age. Yikes.
Who Is She?
Let's not be too quick to judge, though. Despite their age difference, the two have been together since 2018, which is very impressive for a player like Jake. Maybe he has finally gotten over Resse and is ready to settle down? Who is Jeanne?
The model is a lot more than just her looks. We've heard she's smart, extraordinary, and loves to read about history. It has also been stated that she's mature for her age.
A Happy Ending
We've heard that the two started their relationship slowly and let it build over time. Maybe years of rushed romance have taught Jake that true love takes time.
Now, their relationship is getting serious and they both seem to be on board with it. The two have resorted to keeping their relationship private, which seems to be the way to go if you want to maintain a healthy relationship in Hollywood.