Inside Jason Sudeikis’ Dating History before and after Olivia Wilde

From dating a model, actress, screenwriter, producer, and director, the "Horrible Bosses" actor Jason Sudeikis has had an impressive dating history. However, his longest relationship was with "Year One" actress Olivia Wilde.

Jason Sudeikis is an accomplished actor who grew up in Kansas and started his career in the 1990s by performing improvisational comedy at Comedy City, formerly ComedySportz, before becoming a sketch writer for "Saturday Night Live."

The award-winning actor, comedian, producer, and writer got his first lead role in 2011 when he starred in "Hall Pass" and is now known for his movies, and series like "Horrible Bosses," "Ted Lasso," "We're the Millers," as well as his colorful love life.

Kay Cannon

"Pitch Perfect" screenwriter Kay Cannon and Jason met in Chicago while working in the improvisational scene, and on June 26, 2004, they tied the knot.

Once the actor started working on "Saturday Night Live," their relationship turned into a long-distance one, and they began having difficulties.

With time, things got worse, and they separated in 2008 and finalized their divorce in February 2010. They did not have any children but remained on good terms.

After starring in "Hall Pass," Jason was asked about his thoughts on marriage and relationships, and he said:

"I believe in marriage, having been married (to '30 Rock' writer/producer Kay Cannon). We were together nine years, married for four, and then separated in 2008. The divorce was finalized during the shooting of this movie."

January Jones

Model and actress January Jones reportedly met Jason after her debut as a host on a "Saturday Night Live" episode in November 2009.

After attending the ESPY Awards in Los Angeles in July 2010, the couple, who also appeared on the red carpet, reportedly started dating as they hit it off after the party.

The pair never made comments about their relationship, but they were under constant media attention, and the comedian joked that paparazzi liked to follow the girl he was dating.

In 2010, when asked about their relationship, Jason stated that he did not want to get into that. When probed further on if he had seen her naked, he revealed that he had.

However, a week later, January commented that he had never seen her naked and would never see that. Despite their comments to the press, their onscreen chemistry during "Saturday Night Live" was when their relationship peaked.

Unfortunately, in January 2011, news outlets reported that distance had caused the couple to end their relationship. According to the actress, neither was willing to sacrifice their career over their relationship and chose to remain friends.

Olivia Wilde

Actress, producer, and director Olivia Wilde first met Jason in May 2011 while she was attending a "Saturday Night Live" wrap party at the show's season 36 finale.

Six months later, they started dating, and in January 2013, the actor proposed to her. In August 2013, Olivia and Jason starred together in "Drinking Buddies" shortly before revealing they were expecting a baby.

The couple welcomed their first child Otis Alexander on April 20, 2014. Two years later, a fan wanted to know when they would get married, and Jason jokingly said:

"I know this isn't my mom because my mom's in the audience. I mean, I believe we won't get married until weed is legal in every state."

Shortly after, the actress confirmed she was pregnant again, and in October 2016, they welcomed their second child, Daisy Josephine. The couple continuously celebrated each other while becoming intentional parents.

Olivia and Jason never gave up their social lives and prioritized their weekly date nights. Four years after welcoming their second child and seven years after they got engaged, the couple confirmed their relationship was over.

Despite their separation, inside sources revealed they had been great co-parents as their kids will always be their number one priority.

However, in April 2022, Jason and Olivia made the news after he served her child custody papers. The actress was shocked to receive the documents because she was on stage at CinemaCon in Las Vegas promoting her film "Don't Worry Darling."

The actress responded to his filing in August 2022, accusing him that his actions were not in their children's best interests. The "Horrible Bosses" actor apologized for how the process server did her job as he had no intentions of publicizing their private matter.

Despite the custody battle, Olivia wants what's best for her children. However, she said in an interview that she trusts Jason to be a good parent when the kids stay with him.

While she does not know if her children will go into the entertainment industry like their parents, she has noted that Otis loves singing and thinks of himself as Moana because he loves the movie.

According to Jason, their son is also a huge Beyoncé fan, and the musician also sent him a signed birthday card when he turned two. He is also encouraging his son's passion for basketball because the boy loves dunking basketballs.

The actor once reminisced about his son's fourth birthday as they had spent the day at Disneyland and took their son on Space Mountain. Jason revealed that Otis did not like it and that Olivia was so scared.

While their son was named after Otis Redding, their daughter, who shares the same initials as Jason, was named after Olivia's cousin Daisy, and both couples' family's ancestral love for Joseph and Josephine.

In an interview, he also said that his daughter would do anything for a laugh. She seemed to have inherited his comedic traits. His children would also give him advice about structure and life.

Daisy has added being an actress to her resume as she starred alongside her mother in the movie "Don't Worry Darling," and the director revealed that she did a good job.

Keeley Hazell

Model and actress Keeley Hazell first met Jason Sudeikis in 2014 while filming "Horrible Bosses 2," where she starred as Chris Pine's character's assistant.

According to an insider, they remained friends and got closer leading to the rumors that they were dating in February 2021. However, the insider revealed that the actor was not ready for a relationship at the time.

Though the actor had told his friends that he found the model incredibly attractive, he had a crush on her when she was a glamour model for Page 3.

They confirmed their relationship in June 2021; by November 2021, they had vacationed together in Mexico while packing on the PDA.

After their vacation, a source hinted that Keeley was ready to take their relationship to the next level, and Jason felt safe and relaxed with her. However, their relationship ended in May 2022.

Besides his known relationships, there have been rumors about who Jason was dating or not dating, and because he likes to joke a lot, people tend to read between the lines, and he gets misunderstood.

In 2010, rumors surfaced that he was dating actress Jennifer Aniston. The rumors started after they co-starred in "The Bounty Hunter," and he revealed his crush on her.

After the director informed the actor that his character in the movie had to have a crush on her character, Jason said:

"I've been sort of working on that for the past 15 years. So that'll be easy to accomplish now. Get on film and make it last forever."

However, the couple never dated, as it was nothing more than him declaring his love for one of his favorite actresses. He also said he had a crush on their other co-star Gerard Butler for the same length as Jennifer.

In 2011, an eyewitness reportedly saw Jason kissing the actress, model, and fashion designer Eva Mendes in her car after the "24 Hour Plays" benefit.

An insider later confirmed the eyewitness reports. According to the insider, they also skipped the after-party to get food. The couple never commented on their relationship status.