Jason Sudeikis Reveals His Biggest Relationship Ick 6 Years After Messy Split From Olivia Wilde: 'Have the Hard Conversations Face-to-Face'

Jason Sudeikis got candid about relationship red flags six years after his messy split from Olivia Wilde.

Sudeikis, 50, revealed his biggest relationship ick while answering a set of speed-round questions in a game of "Risk It For the Biscuit" on the August 5 episode of TODAY With Jenna and Sheinelle.

"What is your biggest relationship ick?" Sudeikis read the question aloud, which seemed to stump him for a moment. "What would it be… hm, I guess, need not be romantic."

"I think it's not communicating well," the Ted Lasso actor declared after stumbling over his words as he mulled the answer over. "Letting communication only happen through texting and emojis."

Host Jenna Bush Hager and her co-host Willie Geist, who was filling in for Sheinelle Jones, chimed in with murmurs of agreement about Sudeikis' relationship red flag.

"You've got to have the hard conversations face-to-face as often as possible," he added.

Ironically, Sudeikis' communication skills have been criticized in the past after his lawyers served his ex and the mother of his children papers in front of an audience at her 2022 film screening.

Wilde was confronted in the middle of her speech by Sudeikis' legal representation while presenting her film Don't Worry Darling at CinemaCon.

The director and Sudeikis never married but were together for almost 10 years. They share a son, Otis, 12, and a daughter, Daisy, 9.

"I know Jason has told me that he did not know [about the timing] and I need to believe that in order to continue," Wilde told "Call Her Daddy" host Alex Cooper in June. "It was incredibly traumatizing."

Sudeikis is currently single and co-parents with Wilde. He made a rare comment about his dating life on a June 2026 episode of the "Friends Keep Secrets" podcast, admitting that being single in his 50s "has its ups and downs."

"I like being in relation to people,” he explained. “I'm not at a point in my life where, you know, it feels good or fulfilling to date numerous people all at once. Yeah, that feels daunting and overwhelming, especially with being a parent."

Since splitting with Wilde six years ago, Sudeikis has been romantically linked to model and actress Keeley Hazell, though the pair reportedly broke up in 2021.

Earlier in the episode, Sudeikis also confessed his first celebrity crush was one of the stars of the 1982 classic, Annie.

"Ann Reinking from Annie," he answered almost immediately after reading the question. "She was Daddy Warbucks’ right-hand woman. She was kind of a love interest. She was in Chicago. I mean, she's a dancer. Great voice."

Geist immediately agreed with Sudeikis' answer, marveling that he was able to unlock such a deep childhood memory.

"What a pull," the anchor agreed. "She was cool and beautiful. She was nice to Annie."