Sophie Winkleman as Zoey Hyde-Tottingham-Pierce | Then
Zoey was known as the gorgeous British ex-girlfriend that Walden got really serious with after his divorce with Bridget. After dating for two seasons, Zoey actually could have been Walden’s fiancée, if it were not for her rejection of his marriage proposal. Walden then discovers that Zoey had been dating another man behind her back and decides to seek revenge.
He ended up leaving her daughter Zoey a ferocious and violent dog for her birthday in hopes of getting back at Zoey and her new lover. That’s some straight up bitterness right there!
Judy Greer as Bridget Schmidt | Then
As we are introduced to Ashton Kutcher’s character, it is revealed that he was deeply heartbroken from his divorce with his ex-wife, Bridget. He, apparently, loved her so deeply that he was even willing to take his own life, knowing she didn’t want to take him back.
Though she initially refuses to reconcile with him due to his immaturity, she somehow changes her mind when she finds out he started dating another girl. She then comes to the beach house begging for him to take her back, to which Walden responds with a finalization of their divorce. Ouch!
Judy Greer as Bridget Schmidt | Now
You’ve probably seen Judy Greer in many shows and films already as the actress has an astoundingly long filmography list. The actress, director, model, and author is well known as a character actor, appearing in a wide variety of dramatic and comedic films.
She’s also well-respected for her voiceover work in animated shows such as StoryBots and Archer. Judy’s most recent and popular work can be seen in the hit films, Ant-Man and the Wasp, Halloween, and Driven.
Sophie Winkleman as Zoey Hyde-Tottingham-Pierce | Now
Something particularly surprising about this British beauty is that she is actually considered royalty! Sophie Winkleman is the wife of Lord Frederick Windsor, son of Prince Michael of Kent, the late Queen Elizabeth II’s first cousin. As such, she’s actually known as Lady Frederick Windsor.
The English actress, though basking in royalty, still went on into her acting career, voicing a character on the show Milo Murphy’s Law. She’s also currently filming a new show called Trust, featuring Donald Sutherland and Hilary Swank.
Melanie Lynskey as Rose | Then
Rose became one of the main characters of the show, and one of the crowd’s favorites as well! What Charlie thought would be a one night stand, developed into an obsession in which Rose becomes his stalker, only living a few houses down.
Later on in the show, Charlie somehow eventually falls for her and the two decide to get engage and run off to Paris together. Unfortunately, Charlie’s character dies before they are able to tie the knot.