Jason Segel's Romantic Connections: From Michelle Williams to Linda Cardellini and More

Jason Segel has had his fair share of high-profile relationships and romance rumors. The actor was in a well-known relationship with his former Freaks and Geeks costar Linda Cardellini in the early 2000s, and also dated Oscar nominee Michelle Williams from 2012 to 2013. Additionally, Segel has been linked to Drew Barrymore and Lindsay Lohan, although these relationships were never officially confirmed.

Not all of Segel’s romantic interests have been in the entertainment industry. During a January 2023 interview on The Late Show With Stephen Colbert, the actor shared that he almost pursued a woman who worked at a local ice cream shop after going through a breakup right before the pandemic. (He and Alexis Mixter ended their eight-year relationship in April 2021.)

Segel recalled that the woman at the ice cream shop said nice things to him about How I Met Your Mother and expressed her love for his movies. She even mentioned how his work had helped her during a tough time. Before handing him his ice cream, she shared a heartfelt message, telling Segel, “Never forget the joy you bring to the world.”

Their meet-cute, however, was later ruined after Segel discovered her joyful message was actually the ice cream shop’s slogan.

Keep scrolling to see which stars Segel has dated over the years:

Jason Segel’s Dating History

Credit: Emma McIntyre/Getty Images

Jason Segel's Dating History: Michelle Williams, Linda Cardellini, Alexis Mixter and More

Jason Segel’s love life has been full of high-profile relationships and romance rumors.

Jason Segel, the actor, was in a relationship with his former Freaks and Geeks costar Linda Cardellini in the early 2000s, and later dated Oscar nominee Michelle Williams from 2012 to 2013. Speculation surrounded his connections with Drew Barrymore and Lindsay Lohan, but these relationships were never confirmed.

Not all of Segel's romantic pursuits have been within the entertainment industry. In a January 2023 interview on The Late Show With Stephen Colbert, he revealed that after a breakup before the pandemic, he almost pursued a woman who worked at a local ice cream shop. Segel and Alexis Mixter ended their eight-year relationship in April 2021.

Segel shared that she had said some really nice things to him about How I Met Your Mother. She expressed her love for the movies and mentioned that they had helped her through a tough time. She also told him to never forget the joy he brings to the world while handing him his ice cream.

Their meet-cute took a turn when Segel later found out that her heartfelt message was actually just the ice cream shop's slogan.

Keep scrolling to see which stars Segel has dated over the years:

Jason Segel’s Dating History

Credit: Mirek Towski/FilmMagic

Linda Cardellini

Segel and Cardellini started dating after playing Nick Andopolis and Lindsay Weir on Freaks and Geeks, which ended after one season in 2000. One year after their breakup in 2007, Segel wrote and starred in the movie Forgetting Sarah Marshall. The film follows his character as he tries to win back an ex who dumped him.

Many speculated that the movie was inspired by his relationship with Cardellini, but Segel neither confirmed nor denied the rumors in an interview with The Los Angeles Times. In April 2008, he said, “I can’t control what people think. I was still very much a child [then], and this was more an amalgamation of a lot of different relationships and breakups I’ve had. People are bound to talk, but she was a great girlfriend.”

Jason Segel’s Dating History

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Chloë Sevigny

In late 2009, Segel was briefly linked to Sevigny after they were reportedly spotted kissing at an HBO Emmys party in Hollywood.

Jason Segel’s Dating History

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Michelle Williams

Segel had a significant relationship with Williams, confirmed by a source in March 2012. Another insider revealed that the couple was more serious and happier than people believed.

Throughout their year-long relationship, the couple enjoyed spending time together in various ways. They went on walks in New York City, took vacations together, and even spent time with Williams' daughter, Matilda, whom she had with the late Heath Ledger.

According to a source in April 2012, Matilda has a great bond with Jason and enjoys his company. Jason is good at entertaining children, which makes their time together even more special.

The couple broke up in February 2013, and they were seen at the same New York craft fair in October 2018. However, a source mentioned that they did not speak to each other during the event.

Jason Segel’s Dating History

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Bojana Novakovic

Segel dated Novakovic briefly in 2013 after his relationship with Williams. They were seen having lunch in Hollywood and going to Disneyland before breaking up less than a year later.

Jason Segel’s Dating History

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Alexis Mixter

Segel and Mixter started dating in 2013, but they kept their relationship private until two years later. Their romance was finally confirmed by Us magazine in January 2015 when they were seen holding hands in Hollywood.

After being together for eight years, the couple decided to break up in April 2021. In a now-deleted Instagram post, Mixter shared, "This is a photo of two best friends. This guy and I have shared so much life together. We have changed each other at a deep level. Our bond was beyond what I could have imagined. We have grown, laughed, cried, and shared so much together."

Mixter acknowledged that maintaining a public relationship was challenging but expressed her commitment to remaining friends with Segel. She emphasized her unwavering support and unconditional love for him.

Jason Segel’s Dating History

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Kayla Radomski

Segel and the actress and dancer were first linked in October 2023 when they were spotted together at Universal Studios’ Halloween Horror Nights. They officially made their red carpet debut at the 2024 Golden Globes. After the event, Radomski shared photos from their night out, celebrating Segel’s nominations for Shrinking.

In a January 2024 Instagram post, Radomski expressed her pride and love for Segel. She captioned a slideshow with, “WOW…… @jasonsegel I am so incredibly proud of you!!!! What a dream. You are absolutely one of the hardest working and most deserving humans on this planet. My Golden Globe Nominee! I love that we got to spend a whole day celebrating YOU and your talent!!! I love you so much baby!”

They continued their outing by gracing the Emmys red carpet later that month. Radomski expressed her gratitude and admiration for Segel's hard work and determination, praising his drive and passion for what he does. She shared on Instagram their date night at the Emmys, expressing how Segel inspires her daily and expressing excitement to see him continue to succeed and create magic in his life. Radomski also thanked Segel for his love and for being the best man she could have ever dreamed of.

In April 2024, Radomski offered fans another peek into their relationship by posting an Instagram selfie of her and Segel on a tropical vacation. The photo was captioned with emojis of a palm tree, flexed biceps, and a red heart, showcasing their love and happiness together.

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