Michelle Williams’ Dating History: From Heath Ledger to Thomas Kail

Michelle Williams’ love life has been a topic of conversation since the start of her career. The actress made her TV debut on Baywatch in 1993 and struck up a romance with costar Jeremy Jackson. They managed to keep their relationship under wraps for nearly two decades, with Jackson revealing that Williams was his “first crush” during a 2011 interview. Williams’ most high-profile relationship started in 2004 with Heath Ledger, who played her husband in Brokeback Mountain. Their love story began on set before the pair welcomed their daughter, Matilda, in 2005. (Ledger died from an accidental drug overdose at age 28 in 2008.) Following Ledger’s death, Williams moved on with some notable partners including Spike Jonze, Cary Joji Fukunaga, Jason Segel, Dustin Yellin, Jonathan Safran Foer and Andrew Youmans. Williams married Phil Elverum in 2018, but the pair split the following year. She later married Thomas Kail, with whom she shares three kids. Keep scrolling to look back at Williams’ dating history:

Michelle Williams’ love life has been a topic of conversation since the start of her career. The actress made her TV debut on Baywatch in 1993 and struck up a romance with costar Jeremy Jackson. They managed to keep their relationship under wraps for nearly two decades, with Jackson revealing that Williams was his “first crush” during a 2011 interview. Williams’ most high-profile relationship started in 2004 with Heath Ledger, who played her husband in Brokeback Mountain. Their love story began on set before the pair welcomed their daughter, Matilda, in 2005. (Ledger died from an accidental drug overdose at age 28 in 2008.) Following Ledger’s death, Williams moved on with some notable partners including Spike Jonze, Cary Joji Fukunaga, Jason Segel, Dustin Yellin, Jonathan Safran Foer and Andrew Youmans. Williams married Phil Elverum in 2018, but the pair split the following year. She later married Thomas Kail, with whom she shares three kids. Keep scrolling to look back at Williams’ dating history:

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.”

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.

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.

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.

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.

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.

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.

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.

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.

Us confirmed in December 2019 that the Manchester by the Sea star was pregnant and engaged to the Hamilton director, with whom she worked on the 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, but the little one’s name was not revealed after she gave birth. Williams and Kail welcomed their third child — her fourth — via surrogate in April 2025.