Macaulay Culkin is one of the most beloved child stars of the 90s. After starring in both Home Alone and Home Alone 2: Lost In New York, the actor became a holiday staple in so many households. Macaulay starred in other popular films like My Girl and The Good Son. After a brief hiatus from acting, he took on roles in more independent films like Party Monster in 2003. He’s occasionally returned to acting over the years with small one-off roles in a few different projects, most recently American Horror Story and The Righteous Gemstones, and also fronted the comedy band The Pizza Underground.

While Macaulay rose to fame as a young kid, he’s grown up in the public eye, and now he’s an adult and has a son of his own. While he seems to keep his personal life out of the public eye for the most part, he has had made headlines for some of his relationships over the years. Find out more about his romantic history here!

Brenda Song

Macaulay has been dating The Social Network star Brenda Song since 2017. The pair met while working on the movie Changeland, which premiered in 2019. Both actors have opened up about how much they love each other. Macaulay admitted that he was “waiting for the other shoe to drop” in a 2020 interview with Esquire. He was relieved to learn that it wouldn’t. “No—sometimes it’s just good,” he said. Brenda similarly complimented how good-natured the Home Alone star is. “You can’t be around him and not be happy,” she told the outlet.

The pair occasionally appeared on each other’s social media and in projects together, but they hit a major milestone in April 2021, when they welcomed their first child together. The pair named him Dakota after Macaulay’s sister, who was killed at age 30 in a car crash in 2008. After welcoming their son, it was reported that the pair had gotten engaged in January 2022, when The Suite Life of Zack and Cody actress was seen with a diamond ring while out and about, but the pair hasn’t publicly announced any marriage plans.

In March of 2023, a report emerged that they had secretly welcomed their second child together. According to Us Weekly, they welcomed newborn boy Carson “sometime before last Christmas” in 2022.

Mila Kunis

Mila and Macaulay dated from 2002 until 2011. (NC1/WENN/Newscom/The Mega Agency)

During his hiatus from acting in the early aughts, Macaulay began dating Mila Kunis, 39, in 2002. Both actors were child stars growing up in the spotlight, and they were often the subject of engagement rumors. Macaulay dismissed the speculation and said that he planned to keep their relationship private in a 2003 interview with 20/20. “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,” he said..

Mila opened up about their relationship in a 2007 interview with Parade. “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,” she said. “He’s an amazing, simple guy, who is probably the most brilliant person I’ve ever met. He’s so, so smart and so aware and so kind and so sweet.”

Unfortunately, Mila and Macaulay split up in 2011. Years after their split, Mila opened up about the breakup in an interview with Marc Maron on his WTF podcast. She said they were “probably not as friendly as we could be,” and explained that there were “too many aspects” that “prevented us from ever moving forward.” Even though she said that the two weren’t on great terms, sources close to the Bad Moms actress told HollywoodLife exclusively that she was happy for her ex after he welcomed his son with Mila. “They had a deep love that Mila will always recognize as something special. She ended it badly, they haven’t talked for years and she isn’t going to reach out to him now,” the insider said. “She can take comfort that he is in a good place. That is what she wants for Macaulay.”

Rachel Miner

Macaulay was briefly married to fellow child star Rachel Miner. (Bei/Shutterstock)

As a young star, Macaulay made headlines when he married fellow actress Rachel Miner when they were both still teenagers. At 17, the couple announced that they planned on getting married in 1998, per Newsweek. After two years, the pair separated and finalized their divorce in 2002. Macaulay opened up about why he chose to get married, and why he and the Alice star split  up in a 2004 interview on Larry King Live. 

“It’s not the norm or the average age but, you’d be surprised how many letters I’ve gotten, we were married 50 years and we got married when we were 17,” he said, before Larry King asked why it didn’t work out. “Why doesn’t any marriage work? You know, it just happened sometimes. You never want something like that to happen. And of course when we got married we thought we’d be together forever.”