Jason Sudeikis, the beloved star of Ted Lasso and former Saturday Night Live cast member, has captured hearts both on screen and in his personal life. Following his highly publicized split from actress and director Olivia Wilde in 2020, fans have been curious about the comedian’s romantic journey and current relationship status. The 49-year-old actor’s dating life has been a subject of considerable media attention, particularly after his amicable co-parenting relationship with Wilde and his subsequent ventures into new romances.
Sudeikis’s relationship history spans over two decades, featuring connections with notable Hollywood figures and culminating in his current romance with model and actress Elsie Hewitt. From his early marriage to writer Kay Cannon to his brief fling with Mad Men star January Jones, and his long-term engagement to Olivia Wilde, each relationship has shaped the actor’s perspective on love and commitment. His journey through heartbreak, healing, and rediscovering confidence has been both public and deeply personal.
The actor’s approach to dating has evolved significantly since his separation from Wilde, with sources noting his transformation from a “dark place” to a more confident and positive mindset. As he navigates co-parenting responsibilities with his two children, Otis and Daisy, Sudeikis has found balance between his professional success and personal happiness. His current relationship with Elsie Hewitt represents a new chapter in his romantic life, one characterized by fun, ease, and mutual understanding of their respective careers and lifestyles.
Current Relationship Status: Dating Elsie Hewitt
Jason Sudeikis is currently dating model and actress Elsie Hewitt, with their relationship becoming public in early 2024. The couple was first spotted together in January 2024, engaging in public displays of affection during an outing in West Hollywood, California. Their chemistry quickly caught the attention of fans and media outlets, sparking widespread speculation about the nature of their relationship.
According to sources close to the couple, Sudeikis finds Hewitt “gorgeous” and appreciates that “she makes him laugh and gives him what he needs right now, which is a little fun and amusement.” The relationship appears to be built on mutual understanding and shared interests, with both parties reportedly comfortable with keeping things relatively casual and enjoyable.
What makes their relationship work is their shared approach to dating in Hollywood. Hewitt, who understands the entertainment industry, “isn’t into anything too serious either” and is described as “easygoing” and someone who “knows the cool places in L.A.” This compatibility has allowed Sudeikis to enjoy companionship without the pressure of immediate commitment, something that appears to suit his current life stage perfectly.
The relationship has continued to develop throughout 2024, with sources indicating that things are “going well” between the pair. Their connection represents a significant step forward for Sudeikis, who has reportedly undergone a “huge transformation” from the difficult period following his split from Olivia Wilde.
Past Relationships and Dating History
Kay Cannon: The Early Years
Sudeikis’s first significant relationship was with writer and director Kay Cannon, whom he met in the late 1990s while performing improv in Chicago. Their relationship developed over several years before they married in 2004. However, the demands of Sudeikis’s career, particularly his work on Saturday Night Live, created challenges for the couple. The actor later revealed in a 2011 GQ interview that he was “unhappy” living away from Cannon while working as a writer for SNL.
The couple separated in 2008 and finalized their divorce two years later in 2010. Despite their split, they have maintained a friendly relationship, demonstrating Sudeikis’s ability to preserve positive connections with former partners.
January Jones: A Brief Hollywood Romance
Following his divorce from Cannon, Sudeikis was linked to Mad Men actress January Jones in July 2010. Their relationship began when they were spotted together at an ESPY afterparty, followed by various public sightings, including lunch dates in Los Angeles and on-set visits during Sudeikis’s film projects.
Sudeikis confirmed the relationship during an appearance on Lopez Tonight, where he playfully acknowledged their romance. However, the relationship was relatively short-lived, ending in January 2011. Sources cited long-distance challenges as a contributing factor to their split, as both actors were managing demanding career schedules.
Olivia Wilde: The Most Significant Relationship
Sudeikis’s most prominent and longest relationship was with actress and director Olivia Wilde. The couple met at a Saturday Night Live after-party in May 2011, with Wilde later recounting on The Howard Stern Show how Sudeikis approached her with the memorable line, “Whatever you’re looking for, you don’t need it.”
Their relationship officially began in November 2011, and by 2012, Sudeikis had proposed to Wilde. The couple welcomed two children during their nine-year relationship: son Otis in April 2014 and daughter Daisy in October 2016. Their engagement lasted over seven years, making it Sudeikis’s most significant long-term commitment.
The relationship’s end came in 2020 when the couple announced their separation. What followed was a highly publicized custody battle that reached its peak in April 2022 when Wilde was served legal documents while speaking at CinemaCon in Las Vegas. The incident created significant media attention and legal complications, with Wilde claiming in court filings that Sudeikis’s actions were “intended to threaten me and catch me off guard.”
The custody dispute was finally resolved in September 2023, with Sudeikis ordered to pay $27,500 per month in child support. Since then, the former couple has maintained a successful co-parenting relationship, with both living in Los Angeles to facilitate shared custody of their children.
Keeley Hazell: A Brief Connection
Between his split from Wilde and his current relationship with Hewitt, Sudeikis was briefly linked to his Ted Lasso castmate Keeley Hazell in 2021. Dating rumors emerged when they were spotted embracing in New York City, but the relationship was short-lived, with reports indicating they split in 2022.
Co-Parenting and Family Life
Despite the challenges of his past relationships, Sudeikis has successfully established a positive co-parenting dynamic with Olivia Wilde. The former couple was recently spotted sharing a friendly hug while taking their children to a playground in Los Angeles on April 6, 2025. This public display of amicability demonstrates their commitment to maintaining a “united front” for the sake of their children.
Sources close to the family indicate that both parents are “deeply devoted” to Otis and Daisy, with their children remaining the top priority. The successful resolution of their custody case has allowed both parents to focus on providing stability and love for their children while pursuing their individual romantic lives.
Looking Forward: Sudeikis’s Transformation
Jason Sudeikis’s journey through various relationships has led to significant personal growth and transformation. Sources describe him as being “a lot more confident” and in a “much more positive place” compared to the “dark place” he experienced during the fallout from his relationship with Wilde. This evolution has been crucial in his ability to open himself up to new romantic possibilities with Elsie Hewitt.
The actor’s current approach to dating reflects lessons learned from past experiences, with an emphasis on fun, compatibility, and mutual respect for career demands. As he continues to balance his successful acting career with his role as a devoted father, Sudeikis appears to have found a healthy equilibrium that allows for both personal happiness and professional fulfillment.
