January, Ashley, Brittany, Demi, Mila...: The many loves of Ashton Kutcher.

Ashton Kutcher’s relationship history is back in the news, with his ex-wife Demi Moore publishing her eye-opening memoir Inside Out. But Kutcher’s relationships have never really been out of the news. Mamamia takes a look back at some of the actor’s most memorable girlfriends and wives.

Abbey McDonald

At high school in the small town of Homestead, Iowa, Kutcher began dating McDonald, the stepdaughter of the school principal.

“She was definitely my first love,” Kutcher is quoted as saying in the book Ashton Kutcher: The Lives And Loves Of The King Of Punk’d. “I worked really hard to go out with her. I sent her flowers and everything.”

But one night during his senior year, Kutcher broke into the school. He was found guilty of third-degree burglary and sentenced to three years’ probation. McDonald broke up with him and went with another boy to the senior prom.

January Jones

When Jones and Kutcher began dating in 1998, Jones was a model and aspiring actress, still a decade away from her Mad Men breakthrough. Jones has claimed Kutcher was not supportive of her acting.

“He was like, ‘I don’t think you’re going to be good at this,’” Jones told GQ in 2009.

They dated for three years, and when Jones scored a role in the Bruce Willis film Bandits, Kutcher became jealous of Willis, according to Moore’s memoir.

“Ashton was convinced they’d had a fling on set,” Moore writes. She adds that Jones later told her she’d had no interest in “that old man”.

Ashley Ellerin

One of Kutcher’s most famous exes is a woman he never actually went on a date with. Kutcher had known Ellerin for a couple of months when they organised their first date in February 2001. He was supposed to pick up the fashion student from her home and take her out to a post-Grammys party. However, he was running late, and when he got to her place, she didn’t answer the door.

“I figured I had screwed up – I had showed up too late,” Ashton later said.

In fact, Ellerin had been murdered that night by the “Hollywood Ripper”, Michael Gargiulo.

Brittany Murphy

In early 2003, Kutcher and Brittany Murphy were starring as loved-up newlyweds in the romcom Just Married. Kutcher’s mother, Diane Portwood, told People that they acted the same way when Kutcher brought Brittany over to her house for visits.

“They’re always holding hands, goofing around, wrestling around on the floor the way people in love do,” she said. “It makes a mother happy to see someone actually care for your child as much as you do.”

The couple were even seen wearing matching rings. But the relationship was brief, and tragically, Murphy died in 2009.

Demi Moore

Kutcher met Moore at a dinner with friends in 2003, and they had an instant connection, despite a big age gap.

Ashton was 25, and Moore was 40, the mother of three girls with ex-husband Bruce Willis. The oldest, Rumer, was just 10 years younger than Kutcher. Moore called Kutcher her “soul mate”, and they married in 2005, with Willis among the guests. She fell pregnant, but lost the baby.

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In Moore’s recent memoir, she writes that she put Kutcher first in the relationship.

“So when he expressed his fantasy of bringing a third person into our bed, I didn’t say no,” she explains. “I wanted to show him how great and fun I could be.”

In 2011, Moore announced she was ending the marriage, following allegations that Kutcher had been unfaithful.

Mila Kunis

Kunis and Kutcher spent eight years starring together in That ‘70s Show. Kunis, who played Jackie, dated Kutcher’s character Kelso, and the then-14-year-old had her first kiss with him on set.

But the couple didn’t start dating in real life till 2012, six years after the show ended. They married in 2015, with their baby daughter Wyatt at the wedding.

Just months after Wyatt was born, Kutcher told Ellen DeGeneres that Kunis was “incredible”.

“She’s the greatest mum,” he said. “I can’t even... I go to work every day and I come home and she’s, like, perfect. And it just seems like everything went amazing. And I know that something probably didn’t go amazing, but she never tells. It’s unbelievable.”

The couple now also have a son, Dimitri. Kutcher says being a parent is his “number-one gig”.

“I am Wyatt and Dimitri’s dad,” he told the Thrive Global podcast. “Everything else is secondary.”