Ashton Kutcher says miscarriage with Demi Moore was 'really painful,' felt like a 'f***ing failure' after divorce

Ashton Kutcher's had many iterations throughout his career and personal life, some of which he reflected on in a wide-ranging interview with Esquire. No topic seemed off limits for the private star who opened up about ex-wife Demi Moore, a relationship he said coincided with his own "a**hole" era, current wife Mila Kunis and friend and former co-star, Danny Masterson, who just stood trial for rape.

Kutcher's career really took off in the early aughts, so much so the good looking actor caught the attention of Moore. When they got together Kutcher and the Ghost star, who is 15 years his senior, immediately became tabloid fodder.

"The moment that information broke [in the press], my life changed," the 44-year-old recalled.

Kutcher was closer in age to Rumer Willis, the eldest of Moore and Bruce Willis's three daughters, than the the actress. But Kutcher was truly in love with Moore, so much so that the thought of being a stepdad didn't scare him. Still, he admitted it was "a lot."

"I was 26, bearing the responsibility of an 8-year-old, a 10-year-old, and a 12-year-old," he recounted, noting he still has a relationship with all three kids. "That's how some teen parents must experience their twenties."

Privately, Kutcher and Moore were trying to have children of their own. The Charlie's Angels actress shared some of those personal details for first time in 2019's best-selling memoir Inside Out. Moore revealed she became pregnant early on in her and Kutcher's relationship, but suffered a miscarriage when she was six months along. She and Kutcher already had a name picked out — Chaplin Ray — for the little girl. The actor, who shares two children with Kunis, was asked if he thinks about the miscarriage differently now.

"Losing a kid that you think you're going to have, and that close to thinking you're going to have a kid, is really, really painful," he said.

Moore, who was previously sober, wrote that she turned to alcohol to cope with the pain. The couple, who wed in 2005, later attempted IVF but fertility treatments were unsuccessful. As a result, her drinking became worse and she started abusing Vicodin.

"Everyone deals with that in different ways," Kutcher remarked, without elaborating on how he coped with their challenges.

"I love kids," he added. “I wouldn't have gotten married to a woman that had three kids if I didn't love kids. The idea of having another kid would have been incredible." The actor has accepted the past, though. "For whatever reason, I had to have that experience."

Kutcher and Moore ultimately ended their relationship in 2011.

"Nothing makes you feel like a failure like divorce," the entrepreneur declared. "Divorce feels like a wholesale f***ing failure. You failed at marriage."

Kutcher was accused of cheating on Moore. Some reports at the time were accurate and some incorrect, but everyone — even his peers — were talking about the scandal. Kutcher said he overheard people talking about their breakup at events, saying things like, "Can you believe what he f***ing did?"

"You own the s*** you did wrong, and you go forward," he stated.

But Moore's buzzy memoir in 2019 made him relive many of those moments as it captured headlines for months. In the book, she confirmed longstanding rumors that she and Kutcher had threesomes as she wanted to "show him how great and fun I could be." She also opened up about the actor's infidelity and said what ended their relationship was when Kutcher cheated on her at pal Danny Masterson's bachelor party. Moore apparently got a Google alert about it. The weekend happened to be their sixth wedding anniversary.

"I was f***ing pissed," Kutcher admitted about Moore's book. "I'd finally gotten to a place where the press had really laid off me and Mila, and my life and my family. And then the next day, [the paparazzi] are at my kids' school."

Kutcher then stopped himself from complaining and said he harbors no ill-will: "I don't want to open anything up in that realm."

Speaking of Masterson, Kutcher was asked to comment on the disturbing allegations about his former That '70s Show co-star. Masterson was charged with allegedly raping three women at his home between 2001 and 2003. A jury was unable to reach a unanimous verdict and a mistrial was declared in December. Kutcher remembered how Masterson was the one on set who kept his co-stars in line in the late '90s.

"He's like, One f***ing rule: Don’t do anything fucking stupid and f*** this up. Because if you f*** it up, you f*** it up for everybody,'" Kutcher recalled, noting how Masterson told everyone not to make any bad decisions, like doing drugs. (Masterson is accused of drugging some of the women he allegedly assaulted.)

Kutcher sounded conflicted when discussing Masterson's legal woes.

"Someday, his kid is going to read about this," the actor explained, but emphasized he's an advocate for those who've been abused. "I wholesale feel for anybody who feels like they were violated in any way."

Kutcher said he hopes Masterson will be "found innocent of the charges brought against him," meaning that he is actually innocent.

"Ultimately, I can't know," added Kutcher. "I'm not the judge. I'm not the jury. I'm not the DA. I'm not the victim. And I'm not the accused. And so, in that case, I don't have a space to comment." After a pause, Kutcher added: "I just don't know."

What Kutcher does know is that he's really happy with his current life. About a year after he and Moore split, the actor began dating his friend and former co-star, Mila Kunis.

"The thing about Mila that made our relationship accelerate was that I had always admired her," Kutcher explained. "Her talents, her skills, her gifts. But I knew that she didn't need me. And she knew that I didn't need her."

For what it's worth, Kunis apparently confirmed to Kutcher he "was an a**hole" for "a good two years" before they got together. As for why they work — besides the fact Kunis is "much cooler" than him — Kutcher said they don't have any secrets.

"We already knew all of each other's dirt," Kutcher explained.

Kunis and Kutcher lead a very normal life by Hollywood standards. When he signed on to star opposite Reese Witherspoon in the upcoming film Your Place or Mine, Kutcher brokered a deal with Netflix in order to keep the movie from filming in Georgia, which offers better tax credits. He had the company take the extra production costs of shooting in L.A. out of his salary so he could be with his family.

"I have young kids, and I like my kids a lot," he shared. "I like spending time with them."

Kutcher was able to keep his gig as den leader for his son's Cub Scout pack and said it was very much worth it.