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.
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.
The 2000s iconography continues with this hot pairing, which lasted on-and-off from 2007 to 2009. At the time, Reese was amid the drama of her divorce from Ryan Phillippe.
The pair appeared together all over town together, heading to Vanity Fair Oscars parties (see pic above) and making out at basketball games.
And let's not forget the adorable - if slightly dishevelled - photos of them cuddling up at Coachella in 2009.
While you don't see much of the two these days, they reportedly split amicably, with Jake even saying in 2016 that “she is … one of the smartest, strongest people I’ve ever met.”
Perhaps these two could pull a JLo/Ben Affleck and re-unite?
We all know how that ended.
Jake and Taylor reportedly dated for only a few months in 2010. But thanks to the artistic brilliance of Taylor's Red album, this moment remains immortalised in pop culture history as one of the greatest romances of all time.
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.
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.
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.
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.
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”.
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