Sarah Silverman’s Boyfriend Revealed if It’s ‘Awkward’ to Work With Her Ex Jimmy Kimmel

From viral sketches to constantly supporting each other’s projects, Sarah Silverman and Jimmy Kimmel‘s bond is quite unmatched. The comedians go way back and have contributed to nearly three decades of legendary relationship comedy.

To promote her new Netflix standup special Postmortem, Silverman went on Jimmy Kimmel Live! to talk to Kimmel and congratulate him on being a new grandfather. She gave him a sandwich bag full of grandfather essentials and a photoshopped picture of him as a wartime veteran. “Listen you’re a grandpa now,” she said. “You need to be a hero. You can’t just be a veteran of KROQ!”

Related: Jimmy Kimmel’s Net Worth Is the Result of Working ‘Harder Than Anyone Else’

So, how do these two have such effortless chemistry? We take a look back at their relationship below.

Did Sarah Silverman & Jimmy Kimmel really date?

Yes, Sarah Silverman and Jimmy Kimmel were in a relationship for seven years, spanning from 2001 to 2008.

The couple first met during the New York Friars Club Roast of Hugh Hefner. Silverman was a performer who also roasted Kimmel during the set by calling him “fat” and saying that he had “no charisma.”

However, the tides turned as she swooned when Kimmel made the first move when they were watching movies as friends. “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 40 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.”

They were named People‘s Funniest Couples in 2008 and the twosome raved about how much they admired each other. Silverman admitted at the time that they “really, really, really like each other.”

“He’s kind and funny and maybe the most thoughtful person I know,” she added. Kimmel shared the same sentiment, “Sarah is funny and smart and good to look at. Plus, she likes fat guys. What more could I ask?”

The couple went on to make lots of public appearances together with the Wreck-It Ralph voice actress making multiple appearances on his late-night show. They developed an ongoing sketch gag where Silverman confessed she was in a torrid love affair with Jimmy Kimmel’s nemesis Matt Damon. Months later, Jimmy retaliated with the gag that he’s also in a love affair, but with Matt Damon’s best friend Ben Affleck.

Why did Sarah Silverman & Jimmy Kimmel break up?

They broke up in 2008, before reconciling in 2009 and calling it quits for good. Silverman opened up about the breakup in an interview with Playboy. “I think Jimmy and I had every intention of spending the rest of our lives with each other. 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.”

The comedians are still on close terms, and praise each other whenever they can.  Kimmel told GQ in 2017 that he and his ex are “like brothers.”

“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,” he said. “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.”

When Silverman was awarded a star on the Hollywood Walk of Fame, Kimmel gave a heartwarming speech for his ex. “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.”

Jimmy Kimmel is currently married to Jimmy Kimmel Live! co-head writer Molly McNearney, and together they share two children. Silverman is currently in a relationship with Rory Albanese, whom she met in 2020. Albanese also works as a writer on the late-night show.

When asked by Howard Stern if it was awkward for her current boyfriend to be connected to her ex like that, Albanese jokingly responded, “Yeah, no, I know. I just learned that today.”

“It’s kind of funny because I met Jimmy sort of unrelated to Sarah, at an event and we sort of hung out a little and started talking. And then I randomly got a call from him that he needed somebody at the show and I had the resume, so I jumped,” the Daily Show alum said. “But I did say to Sarah at the beginning of it if this is at all awkward, I will not do this, so just tell me. But it hasn’t been awkward at all.”

The radio interviewer also quipped, “There’s a famous story. I hope I’m not telling something out of school, that when you were first with Sarah, that she would scream Jimmy’s name during sex.”

“I still do,” Silverman said, while Albanese added, “By the way, I prefer it. That’s my kink! I like to pretend I’m Jimmy.”