Uploaded August 2026 | Updated September 2026, 2 weeks ago

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Jason Sudeikis and Olivia Wilde's breakup became one of Hollywood's most dramatic splits, culminating in Olivia being served child custody papers while she was onstage at CinemaCon promoting Don't Worry Darling. Needless to say, it quickly made headlines.
But what many people don't realize is that Olivia wasn't Jason's first serious relationship. So let's take a look at the women who have been part of his life over the years.

Chapters:

00:00 - The Olivia Wilde Breakup
00:30 - Marriage to Kay Cannon
02:09 - Romance with January Jones
03:01 - Relationship with Olivia Wilde
07:45 - Rumors with Keeley Hazell
08:22 - The CinemaCon Incident

#JasonSudeikis #DatingHistory #tedlasso #oliviawilde

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Rumour Juice team uncovers mysterious stories of your favorite stars, reveals their life dramas, and shares the most relevant news from the world of Hollywood.

We also go into the details of Hollywood romance stories. Affairs, break-ups, divorces, and beautiful love stories are things that happen in our lives. Well, celebrities are not an exception to that, so let's explore this side of their lives together.

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