A long time before there was Red (Taylor’s Variation), Jake Gyllenhaal was hectic cracking Gyllen-hearts remaining and correct. Typically, the 41-year-dated star has received numerous prominent romances – away from fellow actors Kirsten Dunst and you will Reese Witherspoon to pop symbol Taylor Quick – a few of just who had been co-celebrities, designers, or activities.

Gyllenhaal’s relationship background went within the microscope not too long ago from the wake regarding Taylor Swift’s 2021 lso are-discharge of their 2012 album Reddish. While it’s maybe not been downright verified by the Swift herself, certain music towards record, especially breakup anthem “All of the As well Well,” can be nods in order to the girl short term, three-few days relationship with brand new actor. Gyllenhaal, who’s 9 decades over the age of Quick, and whose latest spouse was fifteen years his junior, features experienced a good lash off scrutiny of Swifties that happen to be, will We state, skeptical of their relationship activities.

Regardless if you are an effective Swiftie doing all of your research towards the Taylor’s exes or good Brokeback Hill stan, it’s enjoyable for taking a visit down recollections lane and don’t forget all of the brands inside Gyllenhaal’s little black guide. Very sit and invite Gyllenhaal’s dating record to take your on a holiday – back to the first aughts, back into the Donnie Darko months, to as he is actually nothing more than an excellent scraggly mustache during the an oversized blazer on arm away from next-girlfriend Jenny Lewis.

2001: Jenny Lewis

Gyllenhaal and you will Jenny Lewis, the previous frontwoman getting indie rockband Rilo Kiley, shared a short connection into the 2001. He and you will Lewis keeps stayed relatives since the, being close and you may help each other’s really works. Gyllenhaal even grabbed Lewis just like the their big date on the Fantastic Planets last year.

2002 – 2004: Kirsten Dunst

Gyllenhaal’s relationship which have star Kirsten Dunst apparently shot to popularity at the lightning rate, transferring together and following your dog long before their next wedding. Once they split up, an associate put out an announcement stating it remained the newest “good family members.” Years after even though, last year, Dunst told Attract one to “it might be nice observe him, however, we are not good friends.” Split.

2006: Natalie Portman

Even when the relationship don’t last enough time, Natalie Portman and Jake Gyllenhaal made for an incredibly precious few once they dated for a few days for the 2006 – though, based on E!, the pair apparently plus old to own an even briefer period within the 2002. Immediately following its broke up inside 2006, Gyllenhaal and you may Portman resided household members as well as mutual the new display screen together with her in 2009′s Brothers. Gyllenhaal even carefully roasted Portman when he shown the woman toward Wasteland Palm Completion Prize last year, quipping, “The woman is a vegan, rendering it very hard when you’re selecting a location to consume.”

2007 – 2009: Reese Witherspoon

That one moves tough. Gyllenspoon’s like was something special. After the girl divorce or separation of Ryan Philippe, Witherspoon become dating Gyllenhaal at the beginning of 2007, and often talked about their relationship to the fresh new drive. Within the , she informed Fashion, “They are extremely supportive. Serve they to say, I am delighted in daily life, and you may I am really fortunate to have a great amount of extremely supportive some one to myself which proper care considerably personally, and, you understand, that’s all you might hope for in daily life. I’m extremely privileged this way.”

He reportedly spent much time that have Witherspoon’s kids, Ava and Deacon, plus observed your family around Ojai towards weekends in which they had stick to Witherspoon’s ranch, be merry, and you will expand produce.

After they separated from inside the later 2009, admirers was heartbroken. But at that time, a source informed Age! you to its spark simply “fizzled.”

Still, inside the 2016, Gyllenhaal talked glowingly regarding his ex, advising Amusement Each week you to definitely Witherspoon is actually, “once i will say regarding every women who I’m close friends which have otherwise had relationships within my lifestyle, one of many wisest, most powerful anybody I’ve previously satisfied.”

2010: Taylor Swift

And simply this way, introducing the Taylor era. Gyllenhaal and you may Swift mutual a very autumnal love this present year when they were earliest saw with her within the New york city. It absolutely was October, they wore scarves, and you will centered on E!, one of its earliest times was reportedly a visit to an enthusiastic apple ranch. It generally does not attract more cozy-sexy than simply you to definitely.

They apparently prominent Thanksgiving with her one to year having Gyllenhaal’s sis Maggie before continuing on to Nashville to summarize the fresh new activities. It had been around this date the few is noticed taking walks arm-in-arm down a sidewalk in Brooklyn, one another that have twice-wide smiles, and Quick carrying the one and only an excellent maple latte inside her left-hand.

Their dating, needless to say, concluded in the . (Though by taking the fresh new words off “Most of the Also Really (10-Second Version) (Taylor’s Adaptation)” as the a real membership of its relationship, they briefly reconnected into the .)

2012: Anna Kendrick, Minka Kelly, Jessica Lowndes

When you are rumors throughout the romances which have stars Anna Kendrick (another co-celebrity out-of their of Avoid from See), Minka Kelly out-of Monday Nights Bulbs, and Jessica Lowndes regarding 90210 was in fact common during this period, none was in fact previously confirmed. An identical seasons, Gyllenhaal is watched holding hands with an unidentified lady from inside the The York Urban area, even in the event specifics of a love never ever emerged.

2013: Alyssa Miller

Football Illustrated model Alyssa Miller apparently met Gyllenhaal at the gym – this might you need to be new motivation I want to start working out – and that sparked a love one endured for around 6 months. The two came across in the New york however, reportedly broke up when Gyllenhaal relocated to La first off filming Southpaw.

2018 – Present: Jeanne Cadieu

And finally, one to provides me to French design Jeanne Cadieu, who was simply first photographed having Gyllenhaal while on a stroll during the Paris in 2018. They’ve kept the like out of the personal vision towards very region; these include hardly ever viewed together with her in public places as well as do not go after one another to the Instagram, centered on Age!.

Within the , Gyllenhaal told Uk Fashion that he intentions to double-upon his very own matchmaking with the near future, fundamentally plus his reference to Cadieu. “Seeing existence since the a thing that try, you realize, fleeting, as well as the globe becoming since it is now, You will find considered my loved ones, I’ve looked to my buddies and you may We have looked to love,” the guy said. “I am a bit less trying to find work, I would say, and much more looking for one to.”