Michelle Williams and Heath Ledger
Who wasn’t totally enamored by the adorable Michelle Williams and the handsome Heath Ledger? Watching them together was like watching a Hollywood dream romance come true. The two began dating in 2004 while working on their film Brokeback Mountain, and welcomed their daughter Matilda a year later. The couple eventually broke up in 2007, and just a year later Ledger died of accidental intoxication from prescription drugs. Although Williams is very private, she has chosen to speak openly about her intense grief over losing the father of her child, and said she and her daughter will both forever have a a giant hole in their hearts. In 2018, Williams quietly married Phil Elverum, and we’re wishing her all the happiness in the world.
Michelle Williams and Jason Segel
When Blue Valentine actress Michelle Williams and How I Met Your Mother star Jason Segel got together in 2012, they decided to keep their relationship under wraps and as low key as possible. The two decided to try and avoid red carpet events together as well as photos featuring any PDA, in an effort to protect their privacy. What we love most about this couple is how Jason Segel embraced William’s daughter Matilda, whose father is the deceased actor Heath Ledger. The relationship reportedly failed because Michelle and her daughter were firmly rooted in Brooklyn, NY while Jason’s career kept him in Los Angeles, making long distance just too complicated.