Jake Gyllenhaal’s Girlfriends List: Why Did He Break up With Taylor Swift?

Jake Gyllenhaal’s dating history reads like a rollercoaster ride, with plenty of high-profile relationships and headline-grabbing breakups. The actor has been romantically linked to several of Hollywood’s leading ladies over the years, from Kirsten Dunst to Reese Witherspoon. However, one relationship looms large over all his other romances – his brief 2010 fling with Taylor Swift.

Gyllenhaal and Swift quickly became an IT couple when they started dating in late 2010. But the fairytale came crashing down when they broke up just months later, allegedly by Gyllenhaal’s choice. 

Jake Gyllenhaal and Kirsten Dunst (2002-2004)

Jake Gyllenhaal dated actress Kirsten Dunst for two years after being introduced by his sister Maggie. The couple shared a home together in the Hollywood Hills and even bought a dog named Atticus. They seemed very much in love, with Dunst gushing about having dinner together every night. But ultimately their romance didn’t last, with busy work schedules and Dunst feeling neglected leading to their split in late 2004.

Natalie Portman (On and Off 2002-2006)

Gyllenhaal and Natalie Portman first sparked romance rumors in 2002 after starring in a play together. Though they shared an onstage kiss, they didn’t confirm a relationship at the time. They reunited in 2006 for their film The Brothers, leading to speculation they had rekindled their flame. Portman spoke about their “intense” connection and close friendship. While it’s unclear if they were ever officially together, Gyllenhaal and Portman maintained a flirty friendship over the years.

Reese Witherspoon (2007-2009)

Gyllenhaal began dating actress Reese Witherspoon, his costar in Rendition, in 2007 shortly after her divorce. They were together for nearly three years and even took her kids to the park and on vacation. There was talk of an engagement and wedding. But ultimately Witherspoon ended things in late 2009 wanting to focus on her career. “No one cheated. There was no drama,” a source told Us Weekly of their amicable split.

Taylor Swift (2010)

One of Gyllenhaal’s most famous exes is singer Taylor Swift. The two began dating in 2010 but broke up after just a few months. Swift was reportedly very hurt by the split and went on to pen multiple songs about the actor like “All Too Well” and “We Are Never Ever Getting Back Together.” Swift and Gyllenhaal broke up before the start of the new year, a source told, “Jake just told her it wasn’t working out.” At the time, Swift was “really upset and hurt” and felt “really burned” by him. 

Swift was left distraught, later pouring her heartbreak into several breakup anthems believed to be about the actor. Her scathing song “All Too Well” has permanently placed Gyllenhaal in the dog house with Swift fans. Over a decade later, Swifties still haven’t forgiven him for the way he supposedly burned the songstress.

Jessica Lowndes (2011)

Shortly after ending things with Swift, Gyllenhaal had a quick rebound fling with 90210 actress Jessica Lowndes. The two were spotted having breakfast together in New York City in April 2011. But their romance soon fizzled out. A source close to Lowndes said she was more interested in the relationship than Gyllenhaal, who still seemed hung up on his very recent split from Taylor Swift.

Minka Kelly (2012)

Gyllenhaal’s romance with actress Minka Kelly was short but dramatic. Kelly initially rejected the Brokeback Mountain star’s advances in early 2012. But after a stint dating Derek Jeter, Kelly had a change of heart and decided to give Gyllenhaal “another chance.” However, their opposite coasts and busy schedules made things difficult from the start. The spark soon died out between the brief couple after just a few dates.

Alyssa Miller (2013-2014)

One of Gyllenhaal’s longer relationships was with model Alyssa Miller, whom he began dating in 2013 after meeting at the gym. Miller spoke glowingly of Gyllenhaal to Us Weekly at the time, calling him “the teacher” when she cooked for him at home. She also praised his supportiveness and kindness. Initially, things were going strong, with Miller accompanying Gyllenhaal to multiple public events. But after nearly a year together, the romance slowly unraveled. Work projects on opposite sides of the country made it hard to spend time together. They finally called it quits in early 2014.

Jeanne Cadieu (2018-Present)

Gyllenhaal has been dating French model Jeanne Cadieu since 2018 but prefers to keep their romance out of the spotlight. “She’s such a good person,” he told Howard Stern in 2021. Though they keep things relatively private, Gyllenhaal and Cadieu remain together as of late 2022.

The fallout from Gyllenhaal’s short-lived romance with Swift has managed to overshadow many of his other relationships over the years. From his early link to Kirsten Dunst, his rekindled connection with Natalie Portman, his three-year relationship with Reese Witherspoon, and his newest long-term love with model Jeanne Cadieu – few made the impact on pop culture lore like his brief time with Swift.