Jennifer Aniston and Reese Witherspoon’s Friendship Timeline

Jennifer Aniston and Reese Witherspoon’s friendship dates all the way back to 2000. The same year that Michelle Williams first joined

Destiny’s Child, reality TV wasn’t yet mainstream, and a new episode of Friends came on the airwaves every Thursday night.

It all began when Witherspoon had a guest-starring role on the NBC sitcom as Rachel Green’s self-absorbed little sister, Jill. “I was 23 years old and had just had a baby. I was nursing Ava on set, and Jen just kept going, ‘You have a baby?’ I was like, ‘I know, it’s weird,’ Reese recalled of their first meeting during a 2019 interview with Harper’s Bazaar, adding: “She was so sweet to me…We’ve been friends ever since.”

While Witherspoon only appeared on two episodes, she and Aniston kept in touch over the years and would later co-star together again in the Emmy-nominated series The Morning Show. Here, take a look back to see how Aniston and Witherspoon went from on-screen sisters to real-life BFFs with their complete friendship timeline.