Long before Jimmy Kimmel would settle down and marry his longtime partner, Molly McNearney, whom he shares two children with — Jane, 6, and William, 3 — the popular talk show host spent five years of his life in a committed relationship with comedienne Sarah Silverman.
The pair, who first met at a celebrity event in 2001 quickly formed a friendship before seeing where things would go if they were to begin seeing one another — and interestingly enough, once they got together, the ex-couple never looked back.
But in July 2008, things started to get rocky in their relationship and they both decided it was best to call it quits. By October of that same year, however, Kimmel and Silverman reconciled before ending their romance once again — for good this time — in March 2009, deciding that they would be better off as friends.
Why Did Jimmy Kimmel Struggle Being Sarah Silverman’s Friend?
In January 2019, the father-of-four made an appearance on Andy Cohen’s Watch What Happens Live where he addressed his longtime friendship with Silverman.
During the interview, Kimmel admits that after his second time splitting with the Wreck-It-Ralph actress, it took him a while to agree to the idea of carrying on being pals with his ex-girlfriend considering they had spent five years of their lives together.
The Hollywood veteran stressed that there was never any bad blood between him and Silverman, nor did their relationship end badly — it simply didn’t work out.
But even though there was really nothing to be angry about, Kimmel says he needed time to adjust to being nothing more but Silverman’s friend, especially since he didn’t share that close of a bond with any of his other exes before her.
“I would say that it took some time, definitely,” the 52-year-old gushed to Cohen. "It definitely took some time. It was never like where we didn’t like each other, hated each other or anything like that. But it definitely took some time to be comfortable enough to be friends again.”
And while 11 years have passed since their breakup, Kimmel has kept his word as Silverman remains one of his closest pals in showbiz.
In September 2018, the latter made an appearance on Jimmy Kimmel Live, and while fans would have probably assumed things were bound to get awkward between the two, it was rather apparent that the two are on great terms with one another.
In fact, Kimmel found it in himself to quiz Silverman about her dating life, to which she responded, saying: "What's going on with me dating-wise? I'm waiting for this tryst with you to be over!”
The New Hampshire native joked that even though Kimmel had been married to McNearney for five years at the time, he would ultimately end up getting back with her, insisting: "I mean, OK, Molly is cute. She's bright, she's funny, she's blonde—whatever! But come on!
“You've got the kids, you've got the marriage...all right. Work it through!" she told him. "You think she's going to wipe your ass when you're old?"
“I don’t do it now,” Kimmel jokingly responded, “so why should she?”
"It's not fair! She gets, like, new woke Jimmy," Silverman quipped. "I had Man Show Jimmy.”
Later on in the interview, the 49-year-old explained why her romance with Michael Sheen didn’t work out, telling her ex that after the actor had moved back to the UK, it ultimately took a toll on their relationship since she wasn’t looking to make the move to Europe herself.
"As you know, he moved back to the U.K. His life is really there, and my life is really not there. But I love him to pieces. But if he's in town and we're both single, we will make love," she jested.
During their five-year relationship, Silverman said she shared a close bond with Kimmel’s parents, previously telling People magazine that while she was initially nervous of their first encounter, it wasn’t long before the actress got so comfortable that she would “put my head on his mom’s lap.”
The famous exes first met at the Hugh Hefner Friars Club Roast in 2001, an event which Kimmel happened to be hosting that night. She recalled their encounter with the publication, gushing: “Jimmy was the host and I was a roaster. He said I was a slut and I called him fat and charisma-less.”
Needless to say, despite their history, Kimmel and Silverman are still close to this day, and by the look of things, the talk show host's wife has no problem with their friendship.