Inside Ashton Kutcher And Mila Kunis' Controversial Friendship With Sean 'Diddy' Combs

The following article includes allegations of domestic abuse and sexual assault.

Ashton Kutcher and his wife, Mila Kunis, have several controversial friends, such as convicted rapist Danny Masterson. Unlike their support for him ahead of his September 2023 sentencing, the couple apparently won't be saying much publicly regarding their now-embattled pal, Sean "Diddy" Combs. The Bad Boy Entertainment founder has been the subject of sexual assault allegations, starting with his ex-girlfriend, Cassie Ventura, who sued him in November 2023. Though he settled the suit a day later, tales of supposed misconduct have followed. Now, Kutcher and Kunis are rumored to be distancing themselves from Combs despite knowing him for over 20 years.

Kutcher met Diddy while they were both working on separate productions with MTV. Combs was running his music competition series, "Making the Band," while Kutcher was hosting the prank series "Punk'd." During a June 2018 joint appearance on "The Late Late Show with James Corden," Diddy revealed he caught wind of Kutcher planning to pull a stunt on him, explaining, "I gave him a call one day, and I said, 'I heard you were going to punk me and I just don't think that's a good idea,'" [via Billboard]. Their friendship grew from there, with Kutcher influencing Combs' decision to run a marathon, and even apparently keeping secrets for the businessman.

One standout moment in their friendship arrived when Ashton Kutcher and Sean "Diddy" Combs went on a jog in 2003. During a September 2019 episode of "Hot Ones," Kutcher revealed that Combs grew tired quickly. With the paparazzi being close by, capturing the two, Diddy asked the "That 70's Show" star to slow down so that the cameras didn't capture him getting winded. According to Kutcher, Diddy could not accept his defeat and began training for the New York marathon.

Combs suffered a leg cramp during the marathon, though he was still able to complete it. His appearance in the run prompted other men of color to focus on their health. The "Last Night" rapper documented his preparation for the race in an initiative called "Diddy Runs the City," which also raised money for several causes. Aside from such wholesome events, Kutcher may have been privy to a much darker side of Combs.

In March 2024, the accusations against Sean "Diddy" Combs took a more serious turn when Homeland Security agents raided several of his homes. His ex-girlfriend, Cassie Ventura, is supposedly cooperating with investigators, and Ashton Kutcher may also be called to give up information, likely due to cryptic comments made during his "Hot Ones" interview.

At the center of the Diddy probe are his parties, which several people have claimed included illicit activity. During Kutcher's sit down with "Hot Ones," he refused to comment on what goes down at Combs' gatherings, stating, "I've got a lot I can't tell." Due to his once-close proximity to Combs, Kutcher is reportedly anticipating the feds calling on him to help with the case. He has not confirmed nor denied if he will be involved in the investigation, and his wife, Mila Kunis, is rumored to be prohibiting him from having contact with the contentious record producer (per the Daily Mail).