Michelle Williams’ Dating History: Heath Ledger, Thomas Kail and More

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Michelle Williams’ Dating History: Heath Ledger, Thomas Kail and More

Since the beginning of her career, all eyes have been on Michelle Williams’ love life. The Oscar nominee’s first known celebrity relationship began in 1993, the same year she made her TV debut in an episode of Baywatch. She embarked on a relationship with her costar Jeremy Jackson after meeting on set, but they managed to keep the news under wraps for nearly two decades. Jackson finally spilled the beans in a 2011 interview with Howard Stern, calling Williams his “first crush.” Williams went on to find true love in 2004 with Heath Ledger, who played her husband in the critically acclaimed romantic drama Brokeback Mountain. They welcomed a daughter, Matilda, in 2005 and broke up two years later. Ledger died from an accidental drug overdose in 2008. “I never gave up on love,” the actress told Vanity Fair in 2018 while reflecting on life after the Dark Knight star’s death. “I always say to Matilda, ‘Your dad loved me before anybody thought I was talented, or pretty, or had nice clothes.’” Williams decided to give love another try six months after losing Ledger. She started dating Spike Jonze in 2008, but their relationship ended up being short-lived. “The timing was impossible,” she admitted to Vogue in 2009. “I thought falling in love again was the only thing that was going to save me from the pain. This erroneous idea: It just makes things more complicated.” After being single for a few years, the Dawson’s Creek alum had high-profile relationships with Cary Joji Fukunaga, Jason Segel, Dustin Yellin, Jonathan Safran Foer and Andrew Youmans. Then, in 2018, she secretly married Phil Elverum. Their union ended less than a year later, and Williams was engaged to Thomas Kail within a matter of months. She and the director are now married and expecting their first child together. Scroll down to see a complete timeline of Williams’ dating history.

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Michelle Williams’ Dating History: Heath Ledger, Thomas Kail and More

Since the beginning of her career, all eyes have been on Michelle Williams’ love life. The Oscar nominee’s first known celebrity relationship began in 1993, the same year she made her TV debut in an episode of Baywatch. She embarked on a relationship with her costar Jeremy Jackson after meeting on set, but they managed to keep the news under wraps for nearly two decades. Jackson finally spilled the beans in a 2011 interview with Howard Stern, calling Williams his “first crush.” Williams went on to find true love in 2004 with Heath Ledger, who played her husband in the critically acclaimed romantic drama Brokeback Mountain. They welcomed a daughter, Matilda, in 2005 and broke up two years later. Ledger died from an accidental drug overdose in 2008. “I never gave up on love,” the actress told Vanity Fair in 2018 while reflecting on life after the Dark Knight star’s death. “I always say to Matilda, ‘Your dad loved me before anybody thought I was talented, or pretty, or had nice clothes.’” Williams decided to give love another try six months after losing Ledger. She started dating Spike Jonze in 2008, but their relationship ended up being short-lived. “The timing was impossible,” she admitted to Vogue in 2009. “I thought falling in love again was the only thing that was going to save me from the pain. This erroneous idea: It just makes things more complicated.” After being single for a few years, the Dawson’s Creek alum had high-profile relationships with Cary Joji Fukunaga, Jason Segel, Dustin Yellin, Jonathan Safran Foer and Andrew Youmans. Then, in 2018, she secretly married Phil Elverum. Their union ended less than a year later, and Williams was engaged to Thomas Kail within a matter of months. She and the director are now married and expecting their first child together. Scroll down to see a complete timeline of Williams’ dating history.

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Jeremy Jackson

The Celebrity Rehab With Dr. Drew alum said on The Howard Stern Show in 2011 that he dated Williams for two years in the '90s. “We messed around,” he claimed. “[She was] my secret rendezvous girlfriend.”

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Heath Ledger

The Emmy winner was in a relationship with the 10 Things I Hate About You star from 2004 to 2007. He died at age 28 in January 2008, just a few months after their split. She later sold their Brooklyn home and moved to upstate New York with their daughter, Matilda, in hopes of living a quieter life.

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Spike Jonze

Williams starred in the director’s 2008 movie Synecdoche, New York. They started dating shortly after Ledger’s death, only to call it quits the following year.

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Cary Joji Fukunaga

The Blue Valentine star was briefly linked to the True Detective director in 2011 after they were spotted together in New York City, but they never publicly confirmed the romance rumors.

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Jason Segel

Us Weekly broke the news of Williams’ relationship with the How I Met Your Mother star in March 2012 after they were introduced by her BFF Busy Philipps. They split in February 2013.

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Dustin Yellin

The Shutter Island star and the contemporary artist were first spotted together in May 2013 after she attended the Met Gala solo. A year later, Us exclusively confirmed that they went their separate ways.

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Jonathan Safran Foer

Multiple sources told Us exclusively in July 2015 that Williams and the Extremely Loud & Incredibly Close author were an item. Their romance fizzled out soon after though.

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Andrew Youmans

The Golden Globe winner was first spotted with the financier in Rome in July 2017, and Us broke the news six months later that they were engaged. However, they called off their engagement later in 2018.

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Phil Elverum

Williams shocked fans when she announced in July 2018 that she secretly married the musician. While she spoke highly of Elverum during their time together — telling Vanity Fair that she was “finally loved by someone who makes me feel free” — news of their separation broke in April 2019.

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Thomas Kail

Eight months later, Us confirmed that the Manchester by the Sea star was pregnant and engaged to the Hamilton director, with whom she worked on the 2019 FX miniseries Fosse/Verdon. A source exclusively revealed in March 2020 that the couple secretly tied the knot. They welcomed their first child together, a baby boy, later that year. Williams confirmed in May 2022 that she was pregnant with the pair's second child, her third.