An Affair, Murder Trial & More: Ashton Kutcher Is Still 'Haunted' By His Painful Past

From the outside looking in, it appears Ashton Kutcher has it all. The successful television and film star is worth an estimated $200 million, and life at home with his wife of five years, actress Mila Kunis, and their two kids, Wyatt, 6, and Dimitri, 4, is as sweet as it gets.

"You think you know how much you can love another person, and then you have a child together, and you realize you didn't know," he's said of raising a family with Kunis. "It's infinitely rewarding."

But things aren't as picture-perfect as they seem for the Two and a Half Men alum. According to an insider, the 42-year-old is still haunted by his past, going all the way back to the brutal 2001 murder of his then-girlfriend, Ashley Ellerin. He and the fashion student were set to head out on a date, but she was stabbed 47 times by a serial killer before Kutcher — who was running late — made it to her Los Angeles apartment.

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"It's an experience that stays with you for a lifetime," notes the insider of the tragic ordeal. "It's scarring."

The actor also carries remorse over how his marriage to Demi Moore ended in 2001 following his high-profile affair. When Moore recently opened up about her "devastating" split from Kutcher, she claimed he admitted to his transgression only after it became news.

"He still has regrets about betraying her," says the insider. "He knows his actions were wrong."

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The actor's marriage to Kunis has given him a chance at redemption in the husband department. The Punk'd alum "puts a lot of effort into their relationship," reveals the insider, explaining that he tries to do something every day to prove how much he loves her. "He'll replace a light bulb that's too high for Mila, make dinner or save the last piece of cake for her. They're small actions, but they mean a lot."

Still, the Bad Moms star keeps Kutcher on a tight leash. "She's forced him to make sacrifices," says the insider, adding that the actor is "happy" to oblige. Now, he won't take on a role unless he discusses it with Kunis, 37, first to see how it will impact the whole family. And he's OK to stay home with the kids when she works.

"When Mila was shooting Breaking News in Yuba County in Mississippi last summer, Ashton minded the fort in L.A.," says the insider, noting that he wants her to feel fulfilled. "Ashton will gladly rearrange his schedule for Mila. He knows that being a wife and mom makes her happy, but it isn't enough. She needs a creative outlet."

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Friends say he's determined not to mess things up and wants her to trust him. "Ashton is home by dinner time every night," says the insider, "and he lets Mila read all his texts and emails to reassure her there's no funny business."

After what happened with ex-wife Moore, Kutcher doesn't want history to repeat itself. In September 2011, it was reported the actor had a one-night stand with a then 22-year-old Sara Leal after a night of partying at the Hard Rock Hotel in San Diego — on his and Moore's sixth wedding anniversary!

The Charlie's Angels alum discovered the news from a Google Alert after reports of the affair began to spread like wildfire over the internet. "Ashton feels bad for not coming clean right away," reveals the insider. "He feels sick that Demi had to find out like that. He knows he should have come forward immediately, and he's so very sorry."

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They separated soon after, and Moore recounted some of the details of their downfall in her 2019 memoir, Inside Out. "Ashton knows he hurt Demi, and he doesn't blame her for resenting him," says the insider. "Of course, he wasn't thrilled with how he was portrayed in the book, but he also knows he had it coming to him. If writing helped Demi find the closure she needed, he's happy."

Kutcher's unfaithful past isn't the only thing that keeps him up at night. In May 2019, the actor was a witness in the trial against Michael Gargiulo, a.k.a The Hollywood Ripper, who was later found guilty of murdering Kutcher's former girlfriend Ellerin.

He teared up in the courtroom as he recalled being hours late for a date with Ellerin, then 22, on the night of Feb. 22, 2001. When he finally arrived at her house, he found her lights on and the door locked and saw what he assumed was a red wine stain on her carpet.

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When she didn't answer, he left. "He'll regret that until his dying day," says the insider. "The word is, he's told friends he still has terrible dreams where he sees Ashley lying in a pool of blood, and he wakes up sweating and crying. The guilt is unbearable sometimes."

The insider says friends hope Kutcher can forgive himself. "Anyone who's known Ashton long can see his experiences have made him a better person," shares the insider, pointing out that he and Kunis are involved in multiple charities and try to give back as often as possible. "He's given away tons of his own money, though he doesn't advertise it," the insider continues. "Ashton's heart is in the right place, and hopefully, one day, it will heal."