Two secret weddings, a painful divorce, Heath Ledger: Inside Michelle Williams' private life.

For years, celebrity watchers have latched strongly onto the “poor Jen” narrative, in regards to the life of Jennifer Aniston, but under the surface, the “poor Michelle” narrative has also been chugging along just as strongly.

Of course, neither Jennifer Aniston or Michelle Williams deserves a “poor” popped on their names like an unwelcome slice of pineapple on a perfectly good pizza, but these are the times we live in.

There seemed to be almost an audible sigh of relief and happiness from Michelle’s fans this week, when it was reported that the award-winning actress and former Dawson’s Creek star had secretly married Broadway producer Thomas Kail.

Her second secret wedding fans had celebrated in the last two years.

Of course, the notoriously private 39-year-old actress didn’t sell her wedding pictures to a magazine or post about her nuptials on her (non-existent) social media channels. Instead, it was confirmed the same way her engagement to Thomas and the news they are expecting their first child was confirmed in December 2019, by a “source” to Us Weekly.

Listen to all the details about Michelle Williams’ secret wedding, along with the biggest entertainment stories of the day, on The Spill. 

Of course, there’s no definitive way to know if this is true or not, but it has been speculated that Michelle and Thomas’ PR teams may have contacted the publication prior to Michelle appearing on the most recent awards season circuit and numerous red carpets where she picked up a slew of awards for her role in the miniseries Fosse/Verdon.

Effectively, letting the engagement/baby cat out of the bag before she set out to spend weeks in front of cameras and microphones.

It’s all part of a delicate path the actress has attempted to walk over the years, finding a balance between doing necessary press for her films while keeping her personal life out of the public eye.

The secrecy has arisen not so much due to the fact that she is unwilling to share her life story, but more centred around a fear of how it would be mistreated in the wrong hands. She once infamously told an interviewer “I would tell you everything, in the spirit of women sharing with each other but the Internet’s an asshole.”

The personal story the four-time Academy Award nominee is protective of began with her first high profile romance with her Brokeback Mountain co-star, the late Heath Ledger.


Michelle and Heath played an unhappy husband and wife in the 2005 American romantic drama, but behind the scenes of the movie, about two cowboys who fall in love but are unable to be together, the co-stars themselves fell deeply in love.

Just before the critically acclaimed movie opened in cinemas, Michelle gave birth to the couple’s daughter, Matilda Rose Ledger, who is now 14-years-old.

The fairytale-like story of two movie stars falling in love just as their careers accelerated with the box office success of Brokeback Mountain, coupled with the sweet way they talked about each other during the film’s press circuitwas a hit with the public who were enthralled by every aspect of their life.

Although the couple no longer wished to participate in joint media opportunities after the movie’s run had ended, they were continually swarmed by paparazzi, most often as they pushed little Matilda in her stroller around Brooklyn.

The media attention intensified when they split after three years together, and five months later, in January 2008, Heath Ledger was found dead of a drug overdose in the New York apartment he was renting at the time.

In her book This Will Only Hurt a Little, Michelle’s Dawson’s Creek co-star and longtime best friend, Busy Philipps, wrote that before Heath’s death, she believed the couple would find their way back to each other.

“I felt sad for both of them, but weirdly, like something would be figured out and it wasn’t the end of the story for them,” she wrote. “They were so young and that baby was the light of both of their lives. They were just working all the time and it was complicated. S–t is always complicated. Especially when you’re 28. And movie stars. With a baby.”

Due to the intense media coverage of her and Matilda following Heath’s passing, with footage from the time showing so many photographers crowding around their car and down their street in packs so dense they could not enter their home, the mother and daughter were forced to leave New York City and move upstate to a more secluded home, in search of safety.

“I lost my city because of the paparazzi descending upon us,” Michelle later told The Daily Beast. “I literally couldn’t hold onto anything. It felt as if things were literally slipping through my fingers. Things were just streaming away from me. I lost my sense of humour. I’m still looking for that.”

Years later, Michelle entered another high profile relationship, but this time she never let it be a source of conversation during any of her press tours.


In 2012, it appeared that Busy Philipps introduced Michelle to her Freaks and Geeks co-star, How I Met Your Mother’s Jason Segel.

Once again, the paparazzi dogged Michelle and her new partner throughout their year-long romance, with photos of them embracing on their way to Broadway shows and taking Matilda on trips to the zoo regularly surfacing across tabloid covers.

The relationship came three years after her once again very private relationship with director Spike Jonze – and four years after the death of Heath, and when the couple appeared to move in together. At the time, the press coverage was very much that Michelle had finally found “the one”.

Then in late 2013, the couple appeared to separate and were not photographed together again.

Michelle Williams and her new husband Thomas Kail. Source: Getty.

Then in 2018, while appearing on the cover of Vanity Fair, Michelle talked about her personal life like never before, even going so far as to say she was about to marry singer-songwriter Phil Elverum, whom she had never publically mentioned before.

She and Phil, who were introduced through a mutual friend, were married in a secret ceremony in the Adirondacks in late 2018, with only a handful of friends and their two daughters in attendance.


The union was particularly special because like Michelle, Phil was also raising a daughter alone after the death of a partner.

His late wife, illustrator and musician Geneviève Castrée, was diagnosed with inoperable stage-4 pancreatic cancer in 2015, four months after the birth of their daughter. She passed away 13 months later, in July 2016, leaving Phil alone with an 18-month-old daughter.

“I never gave up on love,” Michelle said in the Vanity Fair profile when talking about Phil. “I always say to Matilda, ‘Your dad loved me before anybody thought I was talented, or pretty, or had nice clothes'.

"Obviously I’ve never once in my life talked about a relationship,” she went on to say."But Phil isn’t anyone else. And that’s worth something. Ultimately, the way he loves me is the way I want to live my life on the whole. I work to be free inside of the moment. I parent to let Matilda feel free to be herself, and I am finally loved by someone who makes me feel free.”

Around the time of their under-the-radar wedding, Phil packed up his home in Washington and drove across the country to live with Michelle and their two daughters in Brooklyn.

Unfortunately, less than a year after the wedding and Michelle publically calling the relationship "sacred" the still-newlyweds ended their relationship. A painful divorce followed and Phil moved out of the newly shared home with his young daughter.

During her acceptance speech for Best Female Actor in a Television Movie or Limited Series at the 26th annual Screen Actors Guild Awards in January, Michelle said “Tom, I share this with you."

Backstage at that same awards show, she told the press she was taking time off from acting to focus on the birth of her second child and her new life with her fiance, saying, "I haven’t taken a job since Fosse/Verdon. I have something else I have to go do. I’ll be home."

Ultimately, the narrative around Michelle Williams as a victim, unlucky in love or forever broken by Heath Ledger's death was one that should never have existed in the first place.

No matter what life holds for her next, let's hope that's the end of it.

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