Inside Jason Segel's Star-Studded Dating History

Jason Segel has been a comic genius for decades, since his early acting days on "Freaks and Geeks" through his years on "How I Met Your Mother" and his numerous hit films. Throughout his time in the spotlight, Segel has largely managed to keep his private life low-key, despite some A-list partners and long-term romances, both with some of his co-stars and with women who weren't in showbusiness all together.

Now, Segel is basking in the success of his hit Apple TV+ series "Shrinking," and he's enjoying the glory alongside his gorgeous girlfriend Kayla Radomski. The pair have been romantically linked since October 2023, when they were spotted at Universal Studios enjoying a night of fun and fear at Halloween Horror Nights. Since then, she's been effusive in her support and love of her funnyman beau.

Segel's romance with Radomski — who is an actress and professional dancer — came two years after the Golden Globe-nominated actor called it quits from his girlfriend of eight years, Alexis Mixter. However, Segel's lovelife has always played a big part in his career, beginning with an on-set romance to a break-up that inspired his debut feature screenplay, "Forgetting Sarah Marshall."

Jason Segel's first big break came in the cult classic sit-com "Freaks and Geeks," in which he starred as the relatable, awkward, and charmingly goofy Nick Andopolis. Meanwhile, Linda Cardellini played his high school crush, Lindsay Weir. Behind the scenes, Segel and Cardellini sparked a real-life romance that lasted much longer than the short-lived single season sitcom.

In fact, the pair wound up dating for around six years, beginning just after the series ended in 2000. In 2008, Segel starred in "Forgetting Sarah Marshall," which he also wrote, which tells the story of a young man who gets his heart broken in a break-up. Rumors swirled at the time that the film was inspired by his split from Cardellini, although Segel has refuted that. "This was more an amalgamation of a lot of different relationships and breakups I've had," Segel told the Los Angeles Times in April 2008, when asked about the rumors. "People are bound to talk, but she was a great girlfriend."

However, while Cardellini — who went on to get engaged to her childhood pal Steven Rodriguez in 2013 — might not have been the inspiration for the cheating Sarah Marshall character, Segel hinted that their split was the pain that served as a catalyst for writing the story. "I can honestly say that at the age I was when I wrote that movie, 24 or 25 years old, getting over a bad break-up was the most vital, visceral and real pain I had experienced," Segel told Little White Lies in 2023. "It was the biggest thing I'd gone through at that age and I think watching somebody scramble through new emotions in their life is what makes it funny."

In September 2009, Jason Segel was spotted getting cozy and packing on the PDA with "Big Love" actress Chloe Sevigny at an HBO Emmy Awards party in West Hollywood. Segel, who was starring on "How I Met Your Mother" at the time, was reportedly seen celebrating the lavish evening with champagne, cigarettes, and making out with Sevigny at the star-studded event, before they supposedly left the party together.

"At about midnight, Segel and Sevigny were kissing in a corner of the party away from the main bar area," an unnamed source told The Irish Examiner at the time. "They stopped once they realised people were watching them." The source said that the pair left the party not long after people started noticing them making out, but the source couldn't confirm if they actually went home together. However, their reps declined to comment to any outlets and they weren't romantically linked again after the party, making it one of Segel's most high-profile yet briefest celeb romances.

One of Segel's most headline-grabbing relationships began in February 2012, when he sparked a romance with Oscar-nominated actress Michelle Williams. Segel was introduced to Williams by her bestie and his "Freaks and Geeks" co-star Busy Philipps, and the pair hit it off almost instantly. An unnamed source told Us Weekly in March 2012, "They are smitten and very serious." The relationship was apparently exceptionally special for both stars and, most importantly, Segel appeared to get along wonderfully with Williams' daughter, Matilda. The then-7-year-old Matilda — whom Williams shared with the late Heath Ledger — often joined Segel and Williams on day dates around the Big Apple, including a visit to the Bronx Zoo and to a fun Broadway show. 

However, it appears that there were numerous obstacles to Segel and Williams' romance that they couldn't overcome. The pair broke up after a year of dating in February 2013, reportedly due to both being long-distance – Segel lived in Los Angeles while Williams and her daughter lived in New York – and because Williams reportedly wasn't emotionally ready to commit at the time.

In June 2013, several months after calling it quits with Michelle Williams, Jason Segel was romantically linked to Serbian Australian actress Bojana Novakovic. The pair were spotted strolling around Los Angeles together, smiling in the bright summer sun and enjoying each other's company. The pair were also photographed having a great time together at Disneyland in August 2013, as Novakovic went full Magic Kingdom tourist in a Mickey Mouse sweatshirt and sequined Minnie Mouse ears. However, the pair went their separate ways after less than a year.

Notably, in 2010, Novakovic expressed her disinterest in dating other actors, because of the inherent drama that comes with it. "One actor in my life is enough, and that's me," she told Yahoo Australia (via E! News). "With actors it's too easy to go into this world of complaining. Someone will always be better, richer, more loved, do more work. Those dynamics don't interest me."

Jason Segel's longest and most low-key relationship began in December 2013, when he sparked a romance with artist Alexis Mixter, eschewing the Hollywood trend of actors dating other actors. Segel and Mixter kept their burgeoning relationship quiet and private for several years, sparking occasional romance rumors — like when they were photographed walking around Hollywood hand-in-hand in 2015 – before making their big, official red carpet debut in 2016, when they attended a fundraising gala together. However, other than occasional red carpets, the pair largely kept out of the spotlight.

The cute couple unfortunately decided to split up after eight years, which Mixter revealed in an Instagram post shared in April 2021. "This guy and I have shared so much life together. Changed each other at a soul deep level. All for the better," Mixter captioned a photo of herself and Segel (via People). "Change happens and we made the decision quite a while ago to let ourselves grow away from what our relationship had been and into what it was becoming."

While Mixter announced the news in April 2021, Segel suggested the actual split may have happened earlier. The "Shrinking" star sat down for a chat on "The Late Show With Stephen Colbert" and said that he'd gone through a breakup "right before the pandemic, which was very, very sad," implying that their separation may have occurred the year before Mixter actually posted about it.