Jimmy Kimmel And Sarah Silverman Traded Comedic Barbs While Reflecting On Their Past Relationship

Once upon a time, Jimmy Kimmel and Sarah Silverman were a hot ticket comedy couple. The two started dating in 2002 and were on-again, off-again until they split up for good in 2009. Shortly after the split, Kimmel began dating his Jimmy Kimmel Live co-head writer Molly McNearney, and the pair eventually got married and had two children together.

Thankfully, the shared history between Silverman and Kimmel only makes it slightly awkward when she turns up as a guest on her ex’s show, as she did on Wednesday night while promoting her Hulu series, I Love You America. When asked if she was dating anyone, Silverman — who recently parted ways with her long-term boyfriend Michael Sheen — gave Kimmel some good-natured yet awkward ribbing.

“What’s going on with me dating-wise?” she asked, incredulously. “I’m waiting for this tryst with you to be over. Okay, Molly’s cute, she’s bright, she’s funny, she’s blonde, whatever! But like come on!” After Kimmel reminded his ex-girlfriend that he and his wife have, in fact, been married for five years, she lamented that it wasn’t fair.

“She gets like new, woke Jimmy. I had Man Show Jimmy,” she added while making a face, referring to Kimmel’s old Comedy Central program.

Silverman later gave Kimmel a compliment, although admitting that she didn’t “imagine him as a sexual being” anymore. “But you’re handsome, you look gorgeous, you look like a model,” she told him. “You’re doing your beard on like a two.”

But before cutting to commercial Kimmel still managed to get in the last word in after several minutes of torment: “We have the same setting, it’s one of the things we have in common,” he cracked.