Mila Kunis and Macaulay Culkin's Relationship Timeline: A Look Back

Mila Kunis and Macaulay Culkin dated nearly eight years before their 2011 breakup. The former flames were more than just child stars transitioning into the realm of adult actors together. In a way, Kunis and Culkin "grew up together," the Black Swan star told Women's Health in 2009. 

"I don't know if I met him at 27 if it would have been a different relationship," she added.

Perhaps made wary by their experiences in the public eye, the couple kept their relationship incredibly private (despite constant media speculation). Still, Kunis gave us a glimpse into her relationship with the Richie Rich actor during select interviews. For a Hollywood couple, these two were extraordinarily ordinary. Despite their bad breakup, for which Kunis takes the blame, both parties have since moved on and are now married with children — Kunis and husband, actor Ashton Kutcher, are parents to a son and daughter, and Culkin and wife, actress Brenda Song, share two kids together.

Here's a look back at Mila Kunis and Macaulay Culkin's relationship.

2002: Mila Kunis and Macaulay Culkin first meet

In 2006, Culkin told New York Magazine that he met Kunis during a period (following his divorce from Rachel Miner) in which he'd "decided to be abstinent or asexual or whatever." Clearly, the universe had other plans.

At the time, a 27-year-old Kunis was starring on Family Guy, of which Culkin, then 30, was a fan. His love for the animated series helped initiate their romance, reported HuffPost.

2003: Mila Kunis and Macaulay Culkin are first spotted together

By March 2003, Kunis and Culkin were seen out and about in Los Angeles together. That same year, rumors began swirling about their engagement. Culkin had to publicly clarify that he had not proposed to Kunis. 

"We're not engaged. We're not getting married," the Party Monster star told Barbara Walters at the time. "I have a very, very beautiful, very wonderful relationship with somebody. It's going very well … We try to keep our private lives private and our public lives separate … but it's a good thing."

The That '70s Show alum joked about their phantom engagement in an interview with Parade in 2007. 

"I've been engaged. I think I've already been married. And I'm sure I have a child somewhere. I'm waiting to have something else happen," she teased. "No, I'm not married. And no, I'm not engaged. And no, I do not have a child."

September 2007: Mila Kunis opens up about her relationship with Macaulay Culkin

According to Engadget, Kunis and Culkin played World of Warcraft and cooked their own food during their relationship.

"We're incredibly private, and I think we relish the privacy we do actually have and are able to sustain it," Kunis told Parade. "We enjoy each other's company. We like to read books, play video games, watch TV, or go to the movies. And he's an amazing cook. He makes dinner every night."

The Luckiest Girl Alive actress added that Culkin was "probably the most brilliant person" she ever met, describing him as "so, so smart and so aware and so kind and so sweet."

At 20-something, Kunis was settled. 

"I don't remember being single," she told Black Book in late 2009. "I love coming home, taking a bath, and having a glass of wine. I love my life."

That same year, she revealed to Women's Health, "You find a steady rock in your life, and that's all you need. We have our ups and downs, but work through them."

2011: Mila Kunis and Macaulay Culkin break up

Well, there must have been a landslide because Kunis and her "steady rock" announced their breakup in early 2011, reported HuffPost. 

"The split was amicable, and they remain close friends," Kunis's publicist told the New York Post.

In 2012, Kunis assured Elle UK, according to HuffPost, that the relationship had remained a positive experience in her eyes and even helped to shape her identity. 

"Being settled so young really helped," she told the publication. "You know, I wouldn't take back anything in my life, not one thing. I think it all shaped me to be who I am today. There are things that people know about, and there are things that the press doesn't know about, and everything that did occur 100 percent shaped who I am. My ex-boyfriend, my family, my friends, everybody."

While neither party has explained why the relationship ended, Kunis provided some insight into the ordeal in 2016, telling Howard Stern it was difficult to go out in public with the Home Alone star. 

"You couldn't walk down the street with him," she explained, noting that fans "just screamed when they saw him." 

She added, "They didn't know how to react. It wasn't like a normal response to a celebrity. Fans responded in a very abnormal way to him."

Later in the interview, Stern asked Kunis if she was actually in love with her ex, to which she replied, "Honestly, who knows? I just don't know."

During a 2018 episode of Dax Shepard's Armchair Expert podcast, the Bad Moms star admitted that she "fucked up" when it came to her "horrible, horrible" breakup with Culkin. 

"I was an asshole in my 20s, and I'll be the first to admit it," she said. "It's fucked up what I did, and it's fucked up how I did it."

Soon after spilling the breakup tea, Kunis said on WTF with Marc Maron podcast that she and Culkin were "probably not as friendly as we could be." 

"There are too many aspects of it that just prevented us from ever moving forward [from the] past," she vaguely added.