Jimmy Kimmel and Sarah Silverman Joke About Their Romantic History on 'Jimmy Kimmel Live'

Jimmy Kimmel and Sarah Silverman have no bad blood when it comes to their romantic past. The Maestro star, 53, was a guest on Thursday's episode of Jimmy Kimmel Live, prompting a conversation about her and Kimmel's past relationship, as the comedians dated for seven years from 2002 to 2009. 

"We dated for a long time," the 56-year-old late-night host reminded Silverman, who responded, "We dated for a couple years a long time ago." Kimmel corrected her, "A lot more than a couple years," as the Saturday Night Live alum quipped back in response, "Whatever, seven." 

Kimmel and Silverman began dating after Kimmel split from his first wife, Gina Kimmel, in 2002. Following his split from the comedian, the television host began dating his now-wife, Molly McNearney, who is a head writer on Jimmy Kimmel Live. Silverman began dating her current longterm boyfriend, Rory Albanese, in 2020. Albanese serves as a producer on Kimmel's late-night show.

Kimmel couldn't help but point out how his and Silverman's romantic lives have continued to converge following their breakup years ago. "And now, kind of weirdly, Rory, your boyfriend, your longtime boyfriend – who looks almost exactly like me, by the way – is sitting next to my wife there..." Kimmel joked, pointing out Albanese sitting next to McNearney in the audience. "Who looks almost exactly like me," Silverman joked of the blonde McNearney. "Yeah, exactly like you, and Rory and Molly both work here," Kimmel noted. "We have a lot of interconnection."

Kimmel and McNearney tied the knot in 2013 and have gone on to welcome two kids, daughter Jane, 9, and son Billy, 6, together. Kimmel is also dad to daughter Kate Kimmel, 32, and son Kevin Kimmel, 30, with his ex-wife Gina. McNearney has been open about the start of her relationship with Kimmel, telling Glamour in 2014 that they had worked together for six years before they decided to date.

"When I first met him, he insulted me," McNearney recalled of her first interaction with her future husband. "The executive producer brought me into his office and said, 'This is Molly; she's my new assistant.' Jimmy barely looked up from his desk until my EP said, 'She competes in triathlons,' and then Jimmy looked up at me and said, 'That is really stupid! What a waste of time.'" Their friendship would grow over the years and eventually turned romantic, she shared. "All the writers would socialize after the show, and we would just hang out more and more. We really liked each other as friends, and then it just kind of turned. He cooked for me, and that was it. It sealed the deal."