The former couple ended their relationship in 2020 after a seven-year engagement
Credit: Elyse Jankowski/Variety via Getty; Maya Dehlin Spach/FilmMagic
NEED TO KNOW
- Jason Sudeikis is opening up about the “ups and downs” of his dating life
- The actor’s comments came during an appearance on the Friends Keep Secrets podcast
- The Horrible Bosses star was previously engaged to Olivia Wilde for seven years, and shares two children with the actress
Jason Sudeikis admits dating hasn’t been easy.
The Ted Lasso star, 50, appeared on the Tuesday, June 2 episode of the Friends Keep Secrets podcast, hosted by Benny Blanco, Lil Dicky (Dave Burd), and Burd's wife, Kristin Batalucco, and opened up about where his love life currently stands.
After the group discussed siblings and age differences, Sudeikis was asked if he would ever want to have any more kids.
Credit: Kevin Mazur/Getty
“I would if, yeah, if I fell in love,” the Hall Pass alum said.
Sudeikis shares two children — son Otis Alexander, 12, and daughter, Daisy Josephine, 9 — with his former fiancée Olivia Wilde.
The famous exes ended their relationship in 2020 after a seven-year engagement.
Lil Dicky interrupted to ask the actor if he was “a single man,” to which Sudeikis confirmed he is and that single life has its “ups and downs.”
“I like being in relation to people,” Sudeikis explained. “I'm not at a point in my life where, you know, where it feels good or fulfilling to date numerous people all at once. Yeah, that feels daunting and overwhelming, especially with being a parent.”
The Sleeping With Other People star maintained that his kids come first.
“There's also a new thing of anybody I'm dating that they are never number one on the call sheet, as the show biz saying would go, like the kids are,” he said.
“Even probably more so than myself,” Sudeikis continued. “And so then there's that little bit as you get older, you're like, ‘Oh God, I got to make sure my cup's full in order for other people to get the overflow.’ ”
Sudeikis and Wilde met on the set of Saturday Night Live in May 2011. "I met her at a finale party for SNL," Sudeikis told Stephen Colbert in 2017, adding, "We hit it off that night."
She later told Marie Clarie in a 2013 interview that she was unsure whether they would work out.
"I thought, 'He won't be interested in me; I'm not a contender,' " Wilde said. "He was so cool, so funny—I was such a fan of his and had always fancied his speed and his intelligence. He's a brilliant actor with a brain like lightning."
Credit: Steve Granitz/WireImage
Sudeikis popped the question to Wilde with a 1920s Parisian engagement ring in January 2013.
After calling it quits, the pair agreed to joint custody of their two children in 2023. That October, a source told PEOPLE that the two were co-parenting successfully as they both live in Los Angeles.
"They're in a good place," the source said at the time.
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"If there's any resentment over where to live or child custody payments, they certainly don't show it," the source added. "It's a united front. And they are clearly both deeply devoted parents."
In April 2025, Sudeikis and The Invite actress were spotted hugging as they took their kids to a playground.
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