Michelle Williams’s dating history will tell us about how she has struggled over the years to find her knight in shining armor. The actress, who starred in the teen drama Dawson’s Creek, as well as several movies, has been involved with the late Heath Ledger, Jason Segal, and a few other men whose names you will find out very soon.

Currently, Michelle Williams is married to Tom Kail. They had a son in 2020 and named him Hart Kail. Also, at the end of last year, they welcomed baby number two.

Do scroll down and see what we have in store for you because this read will be an exciting one. Here you will learn more about whom the actress got engaged to, whom she married, why the relationships didn’t work out, and most of all, how she dealt with the news of her ex Heath Ledger passing away, who is the father of her eldest daughter Matilda Rose.

Let’s take a quick look at the names of the people that Michelle Williams was involved with in the past.

Michelle Williams Dating History Overview

NameYears Together 
Jeremy Jackson1993
Conor Oberst2000-2001
Bobby Cannavale2003-2004
Heath Ledger2004-2007
Spike Jonze2008-2009
Cary Joji Fukunaga2011
Jason Segel2012-2013
Dustin Yellin2013-2014
Jonathan Safran Foer2015-2016
Andrew Youmans2017-2018
Phil Elverum2018-2019
Thomas Kail2020- Present

1. Jeremy Jackson

In 1993, Michelle Williams met Jeremy Jackson on the sets of Baywatch, after which they secretly were in a relationship for a couple of years. They were teenagers then, and she was his secret rendezvous girlfriend!! Jackson even admitted later on that Michelle was his first love.

2. Conor Oberst

According to Michelle Williams’s dating history, she dated many well-known names. One of them is Conor Oberst, the lead singer of the Bright band Eyes, who dated the actress for about two years until they broke up in 2001. Some of the band’s songs are about Williams.

3. Bobby Cannavale

Michelle Williams and Bobby Cannavale starred in the movie, ‘ The Station Agent’ and started dating in 2003, which lasted for a year. The reason for their split is still unknown.

4. Heath Ledger

Michelle Williams and Heath Ledger first met on the set of the movie ‘Brokeback Mountain’ in 2004, after which they started dating. Williams announced that she was pregnant with a baby girl just a year after she started seeing Ledger.

After giving birth to Matilda Rose, both actors’ lives changed drastically. When Michelle was at work, Heath would babysit and vice versa. Heath enjoyed staying home, doing all the chores, and being a dad, and he even planned to take his baby girl to Australia to view the ocean.

Although the two were engaged and unmarried, Michelle always referred to Heath as her husband. Likewise, Heath also said that he didn’t need a piece of paper to prove his love for Michelle, as she is his soul mate, and they love each undoubtedly. 

In 2007 one of the reasons why the couple split was due to both of them being busy with work all the time and not having time for one another, which made the relationship complicated, although they were still in love. Another reason is that Ledger had suddenly increased taking drugs and heading out to parties which Michelle found inappropriate, especially as they had a baby daughter. Due to Heath’s behavior, Michelle filed for sole custody of Matilda in 2007, as his attitude could have harmed the baby.

The following year in 2008, Heath Ledger left us once and for all after a drug overdose. Although Michelle had broken up with him, the grief and loss were too much for her to bear. The actress had a challenging time mentally getting her head around the fact that Heath no longer existed. This is the most difficult relationship in Michelle Williams’s dating history. Even now, the actress thinks he will walk through the door any minute as she misses him but never fails to keep his memory alive regarding their daughter Matilda.

5. Spike Jonze

Eights months after Heath’s tragic death, Michelle found love and happiness again when she started dating director Spike Jonze. The two kept their relationship out of the limelight for months until they were both seen getting close after attending the screening of Synecdoche, New York, which Jonze directed starring Michelle Williams.

The couple dated for a few months until they split up due to differences in schedules as they were both packed with work and couldn’t spend time together, hampering their relationship. However, Michell, later on, did go on to say that it was impossible for her to love someone so soon after she lost Heath Ledger. The actress always says that no one could take Heath’s place.

6. Cary Joji Fukunaga

Two years after Michelle’s split from Jonez, she was spotted with Jane Eyre director Cary Fukunaga in 2011. The two were seen taking a bite together in Sky Kitchen, after which they walked hand in hand in Brooklyn, New York.

We don’t know if the couple dated, as none of them confirmed the rumors.

7. Jason Segel

In 2012, Michelle Williams dated Jason Segel, who became well-known after acting as Ted Marshall in the comedy series ‘How I met your Mother.’ The couple was seen hanging out together in Brooklyn and Los Angeles several times. The actress looked happier than ever to be with Jason and even said that he turned her life upside down and helped her to get over the loss of Heath Ledger.

But unfortunately, despite finding happiness, Michelle Williams was yet again unlucky in love and split up from Segal due to the relationship being a long distant one which made things complicated as they had to live in different states due to work. The couple had only dated for a year.

8. Dustin Yellin

Michelle Williams’s dating history includes actors, directors as well as the artist Dustin Yellin. The two were seen holding hands while leaving the Met Gala in 2013. Then again, they were spotted together at a birthday party with Matilda, Michelle’s eldest child.

Due to the relationship being kept low-key, we still are confused regarding why the couple decided to go their separate ways after dating only for a year.

9. Jonathan Safran Foer

This time the actress went  into a relationship with the author Jonathan Foer who is famous for his novel, ‘Extremely Loud and Incredibly Close.’ The two met through a mutual friend and instantly connected as Michelle was a bookworm who loved reading.

The couple only dated for a year, leaving the actress single yet again.

10. Andrew Youmans

The financial consultant Andrew Youmans was seen in Rome with Michelle Williams in 2017, where the couple was looking happy and constantly smiling at one another.  They were even spotted in the Bahamas spending New Year’s Eve with Matilda.

Although Andrew liked to stay out of the limelight and away from celebrity functions, everyone questioned Michelle upon seeing her wear a heart-shaped diamond ring at the Golden Globes. People thought a wedding was about to take place, but the actress said it was just a fine piece of jewelry.

Before we knew it, the actress and financial consultant called it quit in 2018.

11. Phil Elverum

American songwriter and producer Phil Elverum decided to tie the knot with Michelle Williams on July 2, which was a secret affair with close friends and family. The couple decided to hide their relationship from the public until September 2018, when the actress announced their marriage in an interview.

She was very happy with Phil as he loved her the way she wanted to be loved and gave her freedom which no one else did, according to Michelle Williams’s dating history.

Shortly afterward, in April 2019, suspicions began to arise regarding the couple splitting up as Michelle was seen attending functions without her wedding ring. Later it was revealed that they had divorced mutually at the beginning of the year as the relationship didn’t work out. A friend of William’s said that the actress had too many responsibilities and jumped into marriage too soon without thinking about what she was in for.

Nonetheless, the actress and musician remain good friends.


12. Thomas Kail

Finally, Michelle Williams has found light in her life and has been happily married to Thomas Kail since 2020, and they have two children together.

The duo met in 2018 when Michelle starred in the award-winning mini-series “Verdon” which Tom Kail produced. However, the two started dating later and were seen shopping for maternity clothes in London in December 2019. A few days after, the actress arrived at JFK international airport wearing an engagement ring, proving that the couple was engaged to one another and expecting their first child too.

In March 2020, rumors spread about the couple getting married secretly after Kail was spotted wearing a wedding band, which was not long before they welcomed their first baby Hart Kail June. Two years later, in November 2022, Michelle gave birth to their second child. The couple still has not revealed the name of the newborn.


Wrapping up

When it comes to Michelle Williams’s dating history, it is visible that the actress went through many rough patches.

The death of Heath Ledger, the father of her firstborn daughter, left the actress broken, after which she desperately sought love but could not settle down.

She dated many men and even got married to Phil Elverum, but sadly the marriage did not even last for a year. Luckily fate had something else waiting for Michelle as she found the perfect man Tom Kail and married him, along with becoming the mother of his two children. Michelle has finally managed to heal from the loss of Ledger, but she doesn’t fail to keep his memories alive for their daughter Matilda Rose.

Currently, Michelle Willams and Tim Kail are a family of five, which include Matilda Rose, Hart Kail, and the newborn baby.

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Rowshan Jahan has an exponential interest in celebrity gossip and is known for his outstanding reporting on the net worth of some of the biggest names in the industry. He covers a wide range of celebrities, including actors, musicians, athletes, and politicians, providing readers with an inside look at the lives of the rich and famous, endorsement updates, also net worth comparison.


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