How Michelle Williams Found Love Again (Her Daughter Played Matchmaker!)

Michelle Williams is engaged to her Fosse/Verdon director Thomas Kail

Michelle Williams has had a long journey towards love.

The actress is engaged to Hamilton director Thomas Kail, who also directed her in this year’s Fosse/Verdon. Williams, 39, and Kail, 42, are also expecting their first child together.

Williams’ daughter Matilda, 14, played matchmaker, a source told PEOPLE. The actress and Kail went public with their love when they were photographed together in London, where she is busy filming Venom 2. Williams was spotted buying baby clothes at Seraphine’s maternity boutique in Kensington.

Her new romance comes more than a year after Williams married indie musician Phil Elverum during the summer of 2018. The two quietly separated in early 2019, but Williams told Vanity Fair shortly after they married that their relationship provided the “radical acceptance” she had been searching for since her romance with ex-boyfriend Heath Ledger, who was Matilda’s father.

“I never gave up on love,” Williams said to Vanity Fair. “I always say to Matilda, ‘Your dad loved me before anybody thought I was talented, or pretty, or had nice clothes.’ ”

Thomas Kail, Michelle Williams
Rodin Eckenroth/WireImage; Frazer Harrison/Getty Images

After Williams and Elverum divorced, the musician told Pitchfork he felt “out of his comfort zone” with their life in New York City.

“We lived a very human existence, and that [celebrity] world mostly felt like an abstraction,” he said of the attention her fame brought.

Williams and Ledger met on the set of 2005’s Brokeback Mountain. The two dated for three years before breaking up in late 2007 — five months before Ledger was found dead of an accidental drug overdose in January 2008.

Primavera Sound Festival - Day 4
Jordi Vidal/Redferns via Getty

After Ledger’s death, Williams largely kept her romantic life private, only briefly talking about some of her relationships in recent years.

The actress dated director Spike Jonze in 2008, six months after Ledger’s death. She later admitted in a Vogue cover story that she realized it was too soon after losing Ledger.

“The timing was impossible,” she said. “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.”

She was later linked to actor Jason Segel in 2012, author Jonathan Safran Foer in 2016 and businessman Andrew Youmans until 2018.

When she revealed she had wed Elverum in 2018, she told Vanity Fair she was opening up about her personal life as a way to help others.

“I don’t really want to talk about any of it. But what if this helps somebody?” she said. “What if somebody who has always journeyed in this way, who has struggled as much as I struggled, and looked as much as I looked, finds something that helps them?”

She continued, “Don’t settle. Don’t settle for something that feels like a prison or is hard, or hurts you. If it doesn’t feel like love, it’s not love.”

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