21 Pictures Of All The Women Jake Gyllenhaal Has Been With

Let's talk about underrated stud Jake Gyllenhaal and how in the world he's single right now. Seriously, how and why and HOW is Jake Gyllenhaal single? Like, why hasn't this guy ever been married? Jake Gyllenhaal is the whole package, Hollywood ladies!

Gyllenhaal found early fame with 2001's Donnie Darko, which was a surprise indie hit. The weird film sparked his career and the hunk went on to appear in indies like The Good Girl, Oscar-winning films like Brokeback Mountain, and darker fare like David Fincher's Zodiac. Gyllenhaal has been nominated for one Oscar for his performance in Brokeback Mountain, though many feel as though his work in 2017's Stronger, 2016's Nocturnal Animals, 2015's Southpaw, and 2014's Nightcrawler were snubbed for Oscar nominations. But do you know how else Gyllenhaal is constantly snubbed? In his love life, y'all. He's a lone, single wolf. The talented, successful, handsome, charming 37-year-old has never been married and, really, hasn't had a relationship last beyond two years. But that lifestyle has led to quite the list of ex-girlfriends. Seriously, Jake Gyllenhaal has dated almost everyone in Hollywood and we're jealous of them all.

Unfortunately, Gyllenhaal hasn't found his fairytale ending, but he has dated everyone from teen drama stars to Oscar winners to straight up models. Below are 21 lucky ladies who have gotten close to snagging Jake Gyllenhaal.

21 Rachel McAdams: Rumors Surfaced When The Duo Filmed Southpaw Together

If there's any leading lady whose love life we should all be jealous of, it's Rachel McAdams. This is the woman who starred in The Notebook with Ryan Gosling, then dated Ryan Gosling like they were the real-life love story. Swoon. And ol' Gosling wasn't the only hot costar with whom McAdams has been linked.

While filming Southpaw, costars McAdams and Gyllenhaal got extra close. The pair were spotted getting cozy dinners together and attending boxing matching. Of course, the boxing matches don't necessarily sound like the most romantic nights out, but they were filming a movie about a fighter… so, you know.

Both McAdams and Gyllenhaal denied the rumors, but then Gyllenhaal dropped this little nugget in an interview: “She has that beautiful darkness but exudes a real, true light. To be dark and light at the same time is as rare as it is infectious.” I'm sorry, but you don't gush that hard about someone you're “just friends” with, right?

20 Taylor Swift: After Briefly Dating In 2010, She Wrote Two Songs About Gyllenhaal

Like every other semi-famous man, Gyllenhaal has dated Taylor Swift and has had the honor of her penning a song in his honor. Swift's “All Too Well” and “We Are Never Ever Getting Back Together” are reportedly about the singer's relationship with Gyllenhaal. Honestly, “We Are Never Ever Getting Back Together” is a true bop, but would you want that song to be about you? Probably not.

Gyllenhaal and Swift only dated for a few months in 2010, but they were very public. On top of their adorable, photographed strolls through NYC, the pair also caused from commotion because they were 9 years apart. It was also around the time when Swift had dated John Mayer, who was 11 years older than her. So, people were like… Um, Tay Tay? You good, girl?

Whatever the case, Gyllenhaal has the honor of having two Taylor Swift songs written about him and that's something.

19 Reese Witherspoon: Things Seemed Perfect, But She Broke His Heart In 2009

WHY DIDN'T THIS WORK? WHY, WORLD? Jake Gyllenhaal and Reese Witherspoon seemed like it should work. Like, it should just have fit. The pair met while filming Rendition in 2006. At the time, Witherspoon's divorce from Ryan Phillippe was pending, so she took it slow with Gyllenhaal. The pair split in 2009, reportedly because Witherspoon was sorting out her emotions from the divorce. This left Gyllenhaal heartbroken, so pretty much imagine a sad puppy. Jake Gyllenhaal definitely looks like a sad puppy when he's heartbroken.

Gyllenhaal still holds Witherspoon in the highest regard. In 2016, Gyllenhaal said Witherspoon was “one of the smartest, strongest people I've ever met.” Shall we all go cry a million tears now because this perfect relationship somehow didn't work out? I say we blame Ryan Phillippe.

18 Alyssa Miller: Jake's Work Out Schedule Ended The Relationship (Yes, Seriously)

No one can deny the fact that Gyllenhaal has dated some of the most beautiful women in the world. Case in point: Alyssa Miller. Miller is a straight up supermodel, who has appeared on the cover of Vogue and worked as a spokesperson for both Guess and Victoria's Secret. What's interesting is that Gyllenhaal's focus on his body may have been what ended this relationship with an actual model. Yes, Gyllenhaal cared too much about his body for Miller's liking.

The pair split while Gyllenhaal was training for his role in Southpaw, which require a lot of time at the gym. When asked about Gyllenhaal and Miller's breakup, the Southpaw director even said, “Literally. I think he broke up with his girlfriend because he was just at the gym every day.”

I mean, no one can complain about Jake Gyllenhaal's body, but also no one wants a gym rat boyfriend.

17 Rachel Bilson: They Low-Key Dated After Bilson Called Off Her Engagement To Hayden Christensen

Oh, what could have been! Rachel Bilson, also known as Summer Roberts on The O.C., began dating Hayden Christensen in 2008. In 2009, Bilson was spotted with an engagement right, though no formal announcement was issued. In 2010, Bilson's representative announced that the engagement between Bilson and Christensen had been halted. It was during this time that Gyllenhaal slid into Bilson's DMs. Well, not really because DMs weren't a thing then, but you get it. It was reported that Bilson and Gyllenhaal were dating, but trying to keep it low-key.

Three months after calling off the engagement, Bilson and Christensen were back on and the Gyllenhaal fling was poof! In 2017, Bilson and Christensen ended their marriage, so maybe there's hope for a little Bilson and Gyllenhaal reunion?

16 Emma Stone: Some Post-Golden Globes Flirtation Sparked Romance Rumors

While Emma Stone and Andrew Garfield were very adorable, we could get into this Stone and Gyllenhaal pairing for real.

During the awards circuit in 2017, at which point Stone was nominated for pretty much every single award for her performance in La La Land, it was reported Stone and Gyllenhaal had hit if off. After the Golden Globes, Gyllenhaal reportedly spent the whole night talking to Stone, because duh. She's gorgeous. After this, Stone and Gyllenhaal were spotted hanging out on several occasions.

Nothing else seemed to come of this hot, new romance, but it would be super adorable. I mean, Emma Stone and Jake Gyllenhaal! Are there any two people who deserve love more than these beautiful beings? Well, we all deserve love, but you know what I'm saying.

15 Natalie Portman: Dated While Filming Brothers, But Remain Very, Very Friendly

Jake Gyllenhaal certainly has a type and that type is his costars. Just kidding, of course. Pretty much all of Hollywood's type is their costars. Hollywood loves hooking up, y'all.

While filming Brothers - in which Gyllenhaal and Tobery Maguire played brothers, because yep it works - Gyllenhaal started dating Natalie Portman. The pair fizzled out, but remain very cordial. In fact, Gyllenhaal presented Portman with the Desert Palm Achievement Award, during which he said, “She's recently announced that she's going to be a new mom to a child who will probably need therapy after seeing Black Swan.”

Gyllenhaal went on to poke fun at Portman's veganism, saying, “It does get hard when you're out to dinner with her.” Um, is that why the couple broke up? They could never decide on what to eat? I mean, that's why about 80% of couples break up, right?

14 Kirsten Dunst: The Pair Were Hot For Two Years, But Dunst Ended Things

Jake Gyllenhaal and Kirsten Dunst! This was the indie couple dream of the early 2000s. Not only were they young, hip, and cool together, but they also lasted a pretty long time by Hollywood's standards. The pair dated from 2002 - 2004, during which time they were seen cuddling, cheering on basketball players at games, and eating salad in Notting Hill.

Dunst reportedly ended things with Gyllenhaal because they were incompatible. Dunst said she wanted to go out on dates, while Gyllenhaal was constantly wanting to stay in. UM, EXCUSE ME? Jake Gyllenhaal is like 'Hey babe, let's stay in and rewatch Game of Thrones and not leave the couch for 48 hours,' and Dunst dumps him over this? Yeah, it seems like Jake Gyllenhaal may, in fact, be the perfect man.

13 Ruth Wilson: They Were Spotted Kissing, But Then Wilson Called Gyllenhaal 'Her Brother', So Like… ?

'Are they or aren't they' seems to be the theme of all Gyllenhaal's relationships. This dude likes to keep it private, but who came blame him? The Hollywood rumor mill is a fickle lover and it's best to not feed into it.

In this situation, it was Ruth Wilson, who Gyllenhaal met while starring alongside in the Broadway play Constellations. Like we said, Gyllenhaal is a sucker for his costars. Hey, I'm just sayin' the best way to hook up with Gyllenhaal is to star in a movie with him.

The dating rumors about Wilson and Gyllenhaal were sparked when they were spotted sharing a kiss. Then, Wilson laughed off the rumors in the weirdest way possible by saying, “We've become like brother and sister a little bit. We spend so much time together.” Well, Gwyneth Paltrow constantly refers to her ex-husband Chris Martin as her brother, so we've heard weirder things.

12 Isabel Lucas: The Duo Stayed Warm In Montreal Together

Isabel Lucas blasted into fame by starring in Transformers: Revenge of the Fallen, as she was the actress who pretty much replaced Megan Fox in the franchise. While Lucas hasn't exactly won any Academy Awards with her acting chops, she's stayed relevant because… well, she's mega hot. Like, she's too hot to not be famous, you know? And Gyllenhaal totally noticed.

It was reported the pair had gotten very cozy in Montreal. To be honest, Montreal is super cold, so they may have just been trying to stay warm. When asked about the relationship, Lucas said, “We're just friends! Our relationship is purely platonic.” The thing is, this is what everyone in Hollywood says and secretly they're married with ten kids. Gyllenhaal and Lucas may have really just been friends, but they also may have been much more.

11 Lily Collins: She Reportedly Thought He Was The "Total Package"

Another movie, another costar. While filming Netflix's Okja, there was a rumored romance between Gyllenhaal and Lily Collins. Collins is absolutely stunning, so we get it. However, the rumor wasn't necessarily about Gyllenhaal pursuing Collins, but the other way around. Yes, it was Collins who was super into Gyllenhaal. (You've still got it, Jakey!)

It was reported that Collin has difficulty finding people to date because of her fame, fortune, and beauty. It's a tough life, y'all. But Collin supposedly felt like Gyllenhaal could be the one to get it. An insider said, “She got to know him while they were filming and thinks he's a total package. She's a little hesitant about making the first move but all her mates are telling her she has nothing to lose.”

Though, it's been nearly a year since Okja came out and nothing materialized in this department. But hey, maybe they're just being sneaky… ? Either way, we can all agree that Lily Collins is so beautiful it hurts to look directly at her.

10 Minka Kelly: They Link Up Whenever They're Both Single And We Are Here For It

At one point, it seemed that Minka Kelly was about to take over Hollywood. She was young, beautiful, and talented. Esquire named her the Sexiest Woman Alive in 2010. She was hot off her portrayal of a cheerleader on the critical darling Friday Night Lights and she had a brief appearance in 500 Days of Summer. The world was hers for the taking. Then, nothing. Kelly pretty much disappeared. However, she didn't disappear from Gyllenhaal.

It's reported Kelly and Gyllenhaal had a fling in 2012, but it didn't stop there. In 2014, it was reported they hooked up again and that they're each other's booty calls. That's right, Gyllenhaal and Kelly supposedly hook up whenever they're both single. Honestly, Gyllenhaal could do much worse for his 'U up?' girl.

9 Jenny Lewis: The Exes Are Literally BFF

Taylor Swift isn't Gyllenhaal's only musically talented ex. Gyllenhaal dated Jenny Lewis, best known as the lead singer in Rilo Kiley, way back in 2001, which feels like 100 years ago. iPhones weren't even a thing yet. Much like his relationship with Dunst, Gyllenhaal and Lewis were an indie dream. I mean, just look at them.

They split, but there's no bad blood between the two. In 2009, Gyllenhaal even took his then-girlfriend Reese Witherspoon to see Lewis perform. That sounds like a nightmarishly awkward situation, but Gyllenhaal is apparently that friendly with Lewis. In 2011, Gyllenhaal even took Lewis to the Golden Globes as his date. Um, Gyllenhaal and Lewis may be legit #exgoals. Instead of settling for an ex who sends you text messages at 2:19 am, wait for the ex who takes you to the GOLDEN GLOBES as his date.

8 Léa Seydoux: The Pair Were Spotted In New York City Together

In 2012, Gyllenhaal was linked to Léa Seydoux. The French actress is best known for roles in films like Blue Is the Warmest Color, Midnight in Paris, The Lobster, and The Grand Budapest Hotel. The pair were spotted walking the streets of New York City together, during which Seydoux's hair was still blue from her role in Blue Is the Warmest Color. However, neither of them commented on the relationship and it seemed to have fizzled out on its own.

We have to note that we're totally into the fact that Gyllenhaal was into the blue hair. He may be one of the hottest guys in Hollywood, but he certainly doesn't conform to any specific notions about what women should look like.

7 Olivia Wilde: The Pair Were Linked While Wilde Was Hollywood's It Girl

I mean, what guy in Hollywood wouldn't want to hook up with Olivia Wilde? She's gorgeous.

In 2011, Gyllenhaal and Wilde were connected on several occasions. There were reports of the pair being extremely flirty at Hollywood's famed Chateau Marmont. Of the flirtation, one insider said, “Olivia was very cool and wasn't fawning over Jake, but seemed to like the attention he was giving her.” Ah, so is that how you get Gyllenhaal's attention? You just act totally cool and chill about it? The pair were also spotted at several New York City restaurants, despite the fact that they insisted they were just friends.

This just so happened to be around the time Olivia Wilde was red-hot. She had also been spotted with Bradley Cooper, Ryan Gosling, and Chris Pine around the same time, so maybe this was just a typical Tuesday fling for her. Either way, we're jealous of Olivia Wilde.

6 Olivia Munn: They Flirted And Exchanged Numbers, But They Really Never Stood A Chance

From one hot Olivia to another hot Olivia. Way back in 2010, Gyllenhaal was linked to Olivia Munn. The pair were spotted speaking closely at a party. Gyllenhaal had been hot off his breakup with Reese Witherspoon and Munn had just broken up with Chris Pine. Of the flirtation, a source said, “Once they met, Jake didn't leave her side the entire night. They looked like they were having fun, both laughing a lot."

At the end of the night, it was reported that Munn and Gyllenhaal exchanged numbers, but there was no news after that. Gyllenhaal was reported just wanting to date around and not take anything too seriously after his split from Witherspoon, so it's likely the Munn romance never had a fair chance to begin with.

5 Anna Kendrick: They Had A Quick Relationship, But Ol' Jake Was Still Hurting Over Reese Witherspoon

Anna Kendrick and Jake Gyllenhaal starred in 2012's End of Watch together, so naturally, they hooked up. The pair had even taken a Labor Day vacation together (SWOON!), but they split shortly after. Gyllenhaal was still in his post-Reese Witherspoon heartache and there was really no chance for the relationship, no matter how adorable Anna Kendrick and Jake Gyllenhaal were together.

Also, how badly did Reese Witherspoon mess up Jake Gyllenhaal? Dude was dating some of the most beautiful, successful, and charming women in Hollywood, but he couldn't stop thinking about the southern belle who broke his heart. Like we said, Reese and Jake totally, completely, absolutely should have worked. Oh, the heartbreak that they aren't together.

4 Dakota Johnson: After An Abrupt Breakup, Gyllenhaal Tried To Win Her Back With A Proposal

OKAY, here's a low-key relationship: Jake Gyllenhaal and Dakota Johnson. Yeah, seriously. They reportedly dated a few years ago. The relationship ended with Gyllenhaal abruptly dumped her for no apparent reason. (Note to all women out there: Even Dakota Johnson gets dumped out of nowhere.) In 2016, it was reported that Gyllenhaal was doing everything to win back the 50 Shades of Grey actress, including a marriage proposal.

What ended up happening is anyone's guess. Clearly, the duo didn't walk down the aisle, so perhaps Johnson simply wasn't willing to forgive and forget the fact that Gyllenhaal randomly dumped her beforehand. Whatever the case, Johnson is now dating Gwyneth Paltrow's ex-husband and Jennifer Lawrence's ex-boyfriend, Chris Martin, because in Hollywood everyone dates everyone.

3 Jessica Lowndes: Gyllenhaal Was Briefly Linked To The 90210 Star

Jake Gyllenhaal doesn't limit himself to A-list celebrities. No offense to Jessica Lowndes or anything, it's just that she's definitely not an A-list celebrity.

In 2011, Gyllenhaal was reportedly dating the 90210 actress. Gyllenhaal and Lowndes were spotted at several locations in New York City together. Of course, this was likely while Gyllenhaal was still doing his heartbroken-over-Reese-Witherspoon thing, so Lowndes never really stood a chance. Sorry, girl.

At this time of Gyllenhaal's relationship with Lowndes, Witherspoon had married Hollywood agent Jim Toth. Gyllenhaal wasn't invited to the wedding. And hey, no judgment on Gyllenhaal's heartbreak over Witherspoon. If anything, it's endearing. He may have dated quite a few women in Hollywood, but he clearly has good taste. I mean, Reese is the QUEEN.

2 Rashida Jones: The Pair Were Spotted Together, But Gyllenhaal Was Also Dating All Of Hollywood

What was even happening at this time?! Like, can someone please explain who Jake Gyllenhaal was actually dating at this time?

Okay, so Gyllenhaal was reportedly still sad over ol' Reese Witherspoon. Literally days after his getaway with Anna Kendrick, Gyllenhaal had a seemingly romantic lunch with Rashida Jones, who seems like she'd be perfect for Gyllenhaal, no? The very next night, Gyllenhaal had dinner with Busy Philipps, who is actually married. And yes, Hollywood people can hang out without getting frisky, as was obviously the case with Philipps and Gyllenhaal. However, the Gyllenhaal and Rashida Jones' outing was reported to be a bit more on the romantic side. Though, nothing serious came of it because Gyllenhaal was basically dating all of Hollywood at the time. What a shame, because we could really root for a Jake Gyllenhaal-Rashida Jones romance.

1 Rooney Mara: Reportedly His Most Recent Romance, But Probably Not

Most recently, it's been reported that Gyllenhaal has been romantically linked to Rooney Mara, which could totally work. Mara fits into his lifestyle, as she's an A-list actress who remains largely as private as possible. And remember how Dunst dumped Gyllenhaal because he wanted to stay in all the time? Well, doesn't it seem like Mara would totally be down for that? Also, literally every girl in the world would want to stay in with Jake Gyllenhaal except Kirst Dunst.

Honestly, Rooney Mara and Jake Gyllenhaal could be a great relationship… except that Rooney Mara is reportedly dating Joaquin Phoenix. It's even been reported that Mara and Phoenix are living together. But then again, Phoenix is such an elusive guy, who knows what's going on there? Also, whoever knows what's going on with these celebrity couples? One day it's Gyllenhaal and Anna Kendrick, then he's with Rashida Jones, then he's sad over Reese Witherspoon. It's impossible to keep up.

Anyway, we're rooting for Gyllenhaal and Mara. Or really, Gyllenhaal and anyone. Poor puppy dog needs to mend his broken heart, get over Reese Witherspoon, and fall in love. We believe in you, Jake!