Hollywood breakups are usually a mess of NDA-protected silence or passive-aggressive Instagram deletions. But then there’s Jimmy Kimmel and Sarah Silverman. Honestly, their relationship trajectory is one of the weirdest, most refreshing anomalies in show business. They didn't just date; they defined a specific era of 2000s comedy, turning their private life into a public bit that actually worked.
If you were online in 2008, you remember the viral chaos. It was the "I’m F***ing Matt Damon" video. That moment wasn't just a funny sketch; it was the peak of a seven-year partnership that most fans thought would end in a wedding, not a press release.
How It All Started: A Roast and a First Kiss
They didn't meet at some swanky Hollywood gala. No, they met at the New York Friars Club Roast of Hugh Hefner in 2001. Jimmy was the host. Sarah was a performer. In true Silverman fashion, she didn't go for a polite greeting. She walked up and told a room full of people that Jimmy was "fat" and had "no charisma."
Brutal. But Jimmy loved it.
For a long time, they were just friends. Jimmy eventually hired her for his prank call show Crank Yankers. They spent nights just watching movies and hanging out. Sarah later told Esquire that their first kiss took forever to happen. They were sitting there watching Broadway Danny Rose, basically nose-to-nose for forty minutes, both too nervous to make the move. When they finally did? "We started making out like crazy," she said. It had been festering.
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By 2002, they were official.
The Reality of Being the "Funniest Couple Alive"
In 2008, People magazine actually gave them that title. It sounds like a lot of pressure, doesn't it? But to hear them tell it back then, the relationship was surprisingly normal. While the rest of the world saw two edgy comedians, Sarah told The New York Times that their life was too "pleasant" to use for stand-up material. Apparently, Jimmy would just tickle her back until she fell asleep.
They were a powerhouse of early-digital-era comedy.
- The Matt Damon video: Sarah surprised Jimmy with it on his show.
- The Ben Affleck response: Jimmy fired back with "I'm F***ing Ben Affleck."
- Shared red carpets: They were staples at the Emmys and various roasts.
But then, things got rocky. In July 2008, they split. Then they got back together. Then, in March 2009, they ended it for good. There was no big scandal. No cheating rumors that stuck. It seemed like a classic case of a long-term relationship simply running its course after seven years.
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Jimmy Kimmel and Sarah Silverman Today: The Ex-Files
Most people can't stand to be in the same room as their ex after a year, let alone fifteen. Yet, Jimmy Kimmel and Sarah Silverman have managed to pull off the "friendly exes" trope without it feeling fake or forced.
It wasn't instant, though. Jimmy admitted to Andy Cohen on Watch What Happens Live that it took time to be comfortable again. You don't just spend every day for seven years with someone and then flip a switch. "It definitely took some time to be comfortable enough to be friends again," he admitted.
The Weirdly Small World of Late Night
Things got even more interesting recently. Sarah’s current boyfriend, Rory Albanese, is actually a writer and producer for Jimmy Kimmel Live!.
Yeah. Read that again.
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Rory joined the show and actually asked Sarah if it would be weird. She said no. Even Howard Stern tried to dig for drama when he had them on his show in 2025, but they both insisted it's fine. Jimmy has even joked on air that Rory looks "almost exactly like me."
Why Their Dynamic Still Matters
In a culture that thrives on "tea" and "beef," seeing two people acknowledge that they were a huge part of each other's lives without trying to erase the past is... well, it's mature.
Jimmy is now married to Molly McNearney (who also works on his show), and they have two kids. Sarah is happy with Rory. When Sarah appeared on Jimmy's show to promote her PostMortem special, the chemistry was still there—not romantic chemistry, but that shorthand you only have with someone who has seen you at your absolute worst.
Actionable Insights for Navigating Your Own Past:
- Time is the only healer: Don't rush a friendship with an ex. If Jimmy and Sarah needed a "buffer period," you probably do too.
- Acknowledge the history: Jimmy once said it makes no sense to erase a big part of your life. You can value the memories without wanting to go back.
- Set boundaries for new partners: If you're going to stay friends with an ex, total transparency with your current partner (like Rory and Sarah have) is the only way it works.
If you’re curious about how they manage to stay so close while working in the same tiny industry, the best thing to do is watch Sarah’s recent guest appearances on Jimmy Kimmel Live!. You can see the genuine respect they have for each other's talent, which is likely the bedrock of why they're still in each other's lives. It’s a masterclass in growing up without growing apart.
Next Steps for You
Check out Sarah Silverman's latest special, PostMortem, on Netflix to see how she’s evolved her comedy since the "Man Show Jimmy" days. You might also want to look up the 2018 Hollywood Walk of Fame ceremony for Sarah; Jimmy’s speech there is a perfect example of how to roast someone you deeply love.