Jason Sudeikis Is ‘Finally Opening Himself Up to a New Relationship’ With Girlfriend Elsie Hewitt

Jason Sudeikis is going strong with latest girlfriend Elsie Hewitt . However, he’s got a ton of other options if it doesn’t work out, according to a source, who says the actor’s now firmly established as one of the most eligible and sought after bachelors in Hollywood.

"The good news for Jason is that he's finally living for himself a little bit and after a lot of false starts, he's finally opening himself up to a new relationship after being in the Ted Lasso bubble for the last five years and having almost no time to devote to anything else, personally or even with his career,” an insider exclusively reveals to Life & Style .

The source adds, “Things are going well with Elsie, but Jason has finally come to understand that he has a lot of options and that women do like him for more than just his incredible success.”

However, the insider reveals that Jason’s in a better place than he was shortly after he and his former fiancée, Olivia Wilde , went their separate ways.

“This is a huge transformation from the dark place he was at a couple of years ago when he was still dealing with the fallout of his relationship to Olivia Wilde,” the source tells Life & Style . “He's a lot more confident and in a much more positive place right now, but what's going to be the trick to making that last? That's a tougher question because even though Jason says he wants to settle down and build toward a new family situation, his trust issues are always going to be a factor against making a new commitment that sticks.”

The insider concludes, “But he's still operating without a map, and trying to figure out what he really needs. Everybody's rooting for Jason and Elsie to make things work, but Jason has proved in the past that even the best relationship can slip through his fingers if he isn't giving it everything he has. He deserves a personal life as successful as his acting career but it's been a major struggle for him to make that a reality.”

Jason, 48, and Olivia, 40, share two children. The Hall Pass star first met Olivia at the Saturday Night Live season 36 wrap party in 2011. They began dating soon after and welcomed their son, Otis, in April 2012, and Jason popped the question later that same year. In October 2016, Olivia gave birth to their daughter, Daisy . However, by November 2020, the couple had called it quits, shocking fans.

While the split seemed to come out of the blue, in January 2021, Olivia was spotted holding hands with Harry Styles , who she had recently directed in her film Don’t Worry, Darling . In April 2022, while she was presenting a clip of the movie at CinemaCon, she was served with child custody documents from Jason while on stage. A spokesperson for the SNL alum later told Deadline that Jason “had no prior knowledge of the time or place that the envelope would have been delivered as this would solely be up to the process service company involved.”