Exes Sarah Silverman and Jimmy Kimmel had the most awkward and relatable exchange on last night’s Jimmy Kimmel Live!

As far as celebrity breakups go, there are a few Hollywood couples who have managed to keep things amicable—dare we say, even friendly—after a split. There’s Chris Pratt and Anna Faris. Demi Moore and Bruce Willis. Debra Messing and Will Chase. But when it comes to the “ultimate” celebrity ex, we might have to go with Sarah Silverman. After all, the funnywoman has managed to remain on good terms with old flames Michael Sheen and Jimmy Kimmel. She’s seriously the epitome of #breakupgoals.

On Wednesday, September 5th, Silverman stopped by Jimmy Kimmel Live! to promote her talk show I Love You, America. And just as she’s done in previous appearances, she didn’t hesitate to crack a few hilariously awkward jokes about her former coupling with the now-married Kimmel.

When asked about her dating status, Silverman quipped she was still hoping to reconcile with Kimmel, who wed comedy writer Molly McNearney back in 2013.

"I'm waiting for this tryst with you to be over!" Silverman joked. "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?"

Sarah Silverman and Jimmy Kimmel also discussed her breakup with Masters of Sex actor Michael Sheen.

“We broke up over Christmas,” Silverman, who announced the demise of her relationship with Sheen in a tweet, said. “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. If he’s in town and we’re both single, we will make love. But he dated someone for a beat during that time when we hung out, and we were just bros. I’m good at separating that, you know?”

In the next breath, Silverman joked she no longer sees Kimmel as a “sexual being.”

“Really?” Kimmel said as the audience erupted in laughter. “You don’t have to make the yuck face!”

See more of Silverman’s sit-down with Kimmel in the video below.


Sarah, if we had to pick a Hollywood celeb to break up with, we’d choose you every time (you know what we mean…).

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