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Late-night host Jimmy Kimmel and Emmy-winning comedian Sarah Silverman started as friends before getting romantically involved in 2002.
From their hilarious sketches on Jimmy Kimmel Live! about having sex with BFFs and frequent collaborators Matt Damon and Ben Affleck to being named People's Funniest Couple Alive, the funny duo proved that laughter was the best medicine for their love affair. Specifically, Silverman told People in 2008 that their relationship worked because they "really, really, really like each other."
"He's kind and funny and maybe the most thoughtful person I know," she added.
Kimmel, meanwhile, said, "Sarah is funny and smart and good to look at. Plus, she likes fat guys. What more could I ask?"
Following a breakup and reconciliation in 2008, Kimmel and Silverman never discovered if the third time could the charm when they split a second time in 2009 after dating for seven years. Although the romance didn't last, they remained friends.
Here's a look back at Jimmy Kimmel and Sarah Silverman's relationship.
September 29, 2001: Jimmy Kimmel and Sarah Silverman first meet
The pair first met in an aptly comedic way at the New York Friars Club Roast of Hugh Hefner in 2001. Kimmel was hosting, and Silverman was obligated to make a joke at his expense. Her blow of choice? Describing her future boyfriend as "fat" with "no charisma," she recalled during a 2007 interview on CNBC Prime.
Thus, a friendship was born. Kimmel hired Silverman for his prank call series, Crank Yankers, and around season 2, they "started hanging out and watching movies together."
"We had known each other for a while, just watching movies and stuff, just being friends," Silverman told Esquire in 2007. "And then one night we were watching Broadway Danny Rose. Jimmy went in for the first kiss, and both of us — we were probably nose to nose for what seemed like forty minutes before either of us had the guts to just go ahead and kiss. But once we did, we started making out like crazy. It had been festering for a very long time."
2002: Jimmy Kimmel and Sarah Silverman begin dating
After they started dating, Silverman addressed the jab that started it all: calling Kimmel "fat."
"It's weird looking back at that. I didn't know him at all back then," she told Entertainment Weekly in 2003. "I can't believe I called him fat. Knowing him now, it's funny because he has such a thin personality."
Despite Kimmel's lack of charisma, the two settled into what appeared to be a sweet and loving relationship.
When asked why she didn't often bring her love life into her work, Silverman told The New York Times in 2005, "It's too pleasant to mine for comedy. He tickles my back until I fall asleep and stuff."
Then there were the Scrabble nights …
"When we have a night alone, like a Saturday night with no kids, we'll go to this restaurant we really like and sit at the bar and play Scrabble on our phones," she revealed to Slate. "We have two games going, so we can go back and forth. There's constant action."
2008: Jimmy Kimmel and Sarah Silverman call it quits, then get back together
In July 2008, People confirmed the longtime couple broke up. However, just a few months later, the outlet reported that Kimmel and Silverman were back on and "taking it slow."
March 2009: Jimmy Kimmel and Sarah Silverman break up again
By the following March, People reported that the relationship was over for good. In 2010, Silverman opened up about the split in Playboy.
"I think Jimmy and I had every intention of spending the rest of our lives with each other," she said, per HuffPost. "I love love. It's my top priority. Jimmy will tell you. I'm a good girl."
She added, "We were together for so long and tried our best to make it work. I can think of him now and don't have that edgy feeling anymore. I just love him to pieces."
Kimmel went on to marry writer Molly McNearney in 2013, and the couple share two children: a daughter, Jane, and a son, Billy. Silverman, meanwhile, dated actor Michael Sheen between 2014 and 2018. Since 2020, she has been romantically linked to comedian Rory Albanese.
February 15, 2017: Jimmy Kimmel says he and Sarah Silverman are "like brothers"
More than friends, Kimmel told GQ in 2017 that he and Silverman were "like brothers."
He added, "It doesn't make sense to me that people would erase a big part of their lives. It's not like we didn't spend every day together for many years. We did, and we have a lot of things in common and mutual friends. I'll see something in the news and think, Oh, my God. I have to tell Sarah about this."
Despite the seeming ease, Kimmel admitted that his friendship with Silverman didn't blossom overnight.
"It definitely took some time to be comfortable enough to be friends again," he told Andy Cohen on Watch What Happens Live in 2019.
November 9, 2018: Jimmy Kimmel lovingly roasts Sarah Silverman as she receives star on Hollywood Walk of Fame
This is truly a twosome whose post-breakup relationship overshadowed their romantic one. Kimmel and Silverman remained close friends following their split, and nearly a decade later, the host even spoke during his ex's Hollywood Walk of Fame ceremony in 2018.
"Who can forget her smash hit viral video, 'I'm effing Matt Damon'? I know I can't," Kimmel said, according to Entertainment Tonight. "Sarah won an Emmy for that appearance on my show. Just to be clear, I have never won an Emmy for an appearance on my show."
He jokingly added, "Sarah and I dated for seven years. She mentioned me in her 300-page autobiography four times. I looked it up last night. She mentioned farting 13 times. It has always been her first love."
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