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A comprehensive list of Jake Gyllenhaal’s past relationships

“I’ll get older, but your lovers stay my age.” - by Erin Christie
  • 17 Nov 2021

All eyes turned to Jake Gyllenhaal this week after Taylor Swift re-released her album, Red (Taylor’s Version), in pursuit of both owning her masters and making her fans cry.

WATCH BELOW: Why Jake Gyllenhaal "didn't marry" Taylor Swift

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While the rumours have never been confirmed, a lot of – most of – the internet believe that Red was inspired mostly by Taylor’s three-month fling with Jake, which led to tunes like All Too Well and We Are Never Ever Getting Back Together.

The songs were re-released, along with the rest of the album, but so was a 10-minute version of All Too Well that ripped the subject even further to shreds, leaving the original for dead when it comes to what a breakup ballad should be.

One of the new, cutting lines is ‘I’ll get older, but your lovers stay my age’, which whipped the Swifties into a frenzy as they searched for evidence that Jake Gyllenhaal had continued to date younger women since breaking it off with Tay.

Taylor claimed on The Tonight Show with Jimmy Fallon last week that she’d written the extra lyrics years ago, ad-libbing the song during a band rehearsal for her Speak Now tour, but she definitely could have added this line to point us to Jake.

And it got us thinking: Who else has he been in love with? So, we’re taking a look at all the women Jake Gyllenhaal's relationship history.

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Jenny Lewis

Beginning in 2001, Jake was dating Jenny Lewis, an actress and musician who was also at the very beginning of her career. Although the relationship was brief, the two held onto a solid friendship, with Jake even taking Jenny as his date to the Golden Globes some ten years later.

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Kirsten Dunst

How’s this for a pair of early 2000s icons? Jake Gyllenhaal dated Kirsten Dunst for two years after meeting in 2002 on the set of Mona Lisa Smile, which his sister also starred in. The couple moved in together, and even adopted a German Shepherd, but they split in 2004.

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Reese Witherspoon

The 2000s iconography continues with this hot pairing, which lasted on-and-off from 2007 to 2009, when Reese was amid the drama of her divorce from Ryan Phillippe. The pair remain friends, with Jake even saying in 2016 that “she is … one of the smartest, strongest people I’ve ever met.”

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Taylor Swift

We all know how that ended.

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Anna Kendrick and Alyssa Miller

Jake’s two next rumoured romances fizzled pretty quickly, if they existed at all, given the rumours were unconfirmed. Jake was linked to Anna while they filmed End of Watch in 2011, but then remained reportedly single until 2013, when he was spotted smooching model Alyssa Miller in New York City, leading to another short fling. While Anna is five years Jake’s junior, Alyssa is the same age as Taylor, so for a hot minute, that lyric might have been onto something.

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Rachel McAdams

We’re trying not to get caught up on the details, but this romance was never actually confirmed. The pair met on the set of Southpaw, and were spotted together numerous times, but both just claimed to be good friends. For what it’s worth, Rachel is two years Jake’s senior, so if they did indeed date, our ‘Jake Gyllenhaal as the subject of All Too Well’ hypothesis suddenly has a hole in it.

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Ruth Wilson

Another unconfirmed romance, Jake was linked to actress Ruth Wilson in 2015 when he was spotted kissing her, again in New York. They were starring on Broadway together at the time, but since the rumours were never confirmed, the fact that she was only one year his junior means our theory remains flawless.

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Jeanne Cadieu

Welcome to the list, Jeanne Cadieu. Jake’s current partner, model Jeanne Cadieu, has been with him since 2018. She’s 25, 16 years Jake’s junior, and we now think we see what Taylor might have been getting at with her new lyric.

Despite the age gap, the pair seem really solid, with Jake telling Vogue last year and mid-pandemic that he has “turned to love” after “seeing life as something that is, you know, fleeting, and the world being as it is now”.

Ready to move on with your love life? Sign up for eHarmony today!

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Erin Christie
Erin Christie
Erin Christie is a writer at WHO (digital), keeping across pop culture, reality TV (especially Survivor), and the occasional fashion trend.

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