Olivia Wilde was seen reuniting with her ex-fiancé Jason Sudeikis on Monday as she dropped off their two children with him. The former couple, who were in a relationship from 2011 to 2020, share son Otis, 12, and daughter Daisy, nine.
Co-Parenting in Action
Wilde, 42, and Sudeikis, 50, shared a warm hug, showcasing their amicable co-parenting relationship. The actress wore a loose-fitting white V-neck T-shirt partially tucked into white jeans, paired with black sneakers with white accents and glossy black sunglasses. Her blonde-highlighted hair was pulled into a low messy bun, and she carried a tan tote bag over her shoulder.
Sudeikis kept it casual in a grey crew neck sweatshirt and dark cargo shorts, accessorizing with a baseball cap, black-framed eyeglasses, and blue Nike sneakers.
Past Relationship Drama
The exes' relationship ended tumultuously when Wilde began dating Harry Styles, whom she cast in her film Don't Worry Darling in late 2020. They got engaged in 2013 but split in November 2020, and Wilde made headlines for dating Styles in January 2021. In 2022, the couple's former nanny told DailyMail.com that Sudeikis was devastated when he realized Wilde had prepared her 'special salad dressing' for Styles, even lying under her vehicle to prevent her from leaving.
Despite infidelity rumors, Wilde denied cheating on Sudeikis, telling Vanity Fair in October 2022: 'The complete horses**t idea that I left Jason for Harry is completely inaccurate.'
Moving Forward
In January 2025, an insider told DailyMail.com that Wilde was emotionally 'moving forward' from her relationship with Styles more than two years after their breakup. 'After the Harry breakup, she really took time off dating and away from the spotlight to focus on herself and her family,' the source said. 'She got way too caught up in that and their relationship became a public spectacle.'
Wilde is now dating art dealer Caspar Jopling, first linked in September 2025.
Harry Styles Engaged to Zoe Kravitz
Meanwhile, Styles, 32, is reportedly engaged to Zoe Kravitz, 37, after an eight-month whirlwind romance. He is said to be eager to start a family with Kravitz, who was recently spotted with a large diamond ring on her wedding finger in Hampstead. A source told Page Six: 'He really wants a baby, he's been telling his friends that.'
Kravitz was previously engaged to actor Channing Tatum, ending their relationship in October 2024, and was married to actor Karl Glusman from June 2019 to December 2020.
