Matthew McConaughey, Janet Jackson and More Surprising Celebrity Duos Who Once Dated

Wait, they dated? Star uncovers some unlikely twosomes who dish about dates with fellow celebs that went nowhere.

Matthew McConaughey & Janet Jackson

Miss Jackson, if you’re nasty! After appearing to deny the rumor that he’d dated the singer, 59, after the pair met at the 2002 Grammy Awards, the Oscar winner fessed up during a game of Plead the Fifth on Watch What Happens Live with Andy Cohen. “We went and had dinner one time,” the now-married 55-year-old admitted. “That was sorta it.”

Sharon Stone & Nelly

Hot in Herre! “This is crazy enough that I actually might believe it,” host Andy Cohen said during a game with the actress. “Sharon, did you go on a date with Nelly?” After a dramatic pause, the 67-year-old replied, “Yes I did.” But it was not meant to be for her and the rapper, 50, now wed to Ashanti. Asked if she went on a second date, Sharon admitted, “No, I did not.”

Kristin Davis & Matthew Perry

The And Just Like That… star recalled on her Are You A Charlotte? podcast, being set up with Matthew, who died in 2023 at age 54, at a dinner party at the height of his Friends fame. Calling him “lovely,” the 60-year-old recalled him sitting next to her and raving about how happy he and his costars were on set. “I was like, ‘Wow, he’s so happy,’” she remembered thinking. “I had been doing Melrose [Place], and it wasn’t the happiest place.”

Drew Barrymore & Christian Bale

The two former child stars had a brief encounter at age 13, but the talk show host, now 50, ghosted the Dark Night star. “We went to see some bloody awful horror film, and that was the end of it,” the 51-year-old recalled to GQ. “She never called again.” Years later, Drew — who went to rehab for the first time at age 13, explained of the fizzled romance on Watch What Happens Live with Andy Cohen, “I had big problems in my world for many years,” adding, “I wasn’t boy crazy.”

Kim Kardashian & Nick Lachey

“We went and saw The Da Vinci Code together,” the former 98 Degrees boy bander, 51, said on Watch What Happens Live with Andy Cohen, of his 2006 night out with the reality star, 44. He later suspected the date was more a publicity stunt than romantic meet-up. “I think there were other things in play on our little rendezvous,” he explained, adding, “She left halfway through and went to the restroom and then, shockingly, there were 25 paparazzi there when we left the theater.”