Inside Macaulay Culkin's Relationship History

Macaulay Culkin, who gained worldwide fame as a child star in the iconic family film "Home Alone" and its sequel, "Home Alone 2: Lost in New York," has been in the spotlight for most of his life. As Culkin was exposed to the dark side of fame at a young age, the beloved actor has maintained a penchant for privacy, keeping his personal life away from the prying eyes of the media.

While details about Culkin's romantic relationships are limited as a result, his love life remains a topic of public conversation. Notably, he married fellow actor Rachel Miner when they were both under 18 and later had an eight-year relationship with Mila Kunis. Following their split, Culkin was in a four-year relationship with Jordan Lane Price before settling down with Disney star Brenda Song, with whom he shares two children.

In a 2020 interview with Esquire, the Disney star highlighted Culkin's unique perspective on Hollywood, sharing, "He's seen the ugly side of this industry; he's also seen the amazing side of this industry. So he can pinpoint exactly what he doesn't want and what he doesn't like about it." Despite the former child star's desire for privacy, his star-studded relationship history remains highly interesting. Here's everything we know about it.

Despite having a relatively short relationship history, Macaulay Culkin got married when he was just 17 years old. In March 1998, Culkin and his then-girlfriend, "Guiding Light" star Rachel Miner, both 17, announced their plans to marry. According to a Los Angeles Times report, the celebrity couple issued a joint statement, which gushed that they were "thrilled to have found each other as soul mates at such a tender age." Culkin and Miner met at the Professional Children's School in New York City and tied the knot in a low-key wedding ceremony in Connecticut in June 1998. 

As they were both below the legal age for marriage, Culkin and Miner had to get their parents' consent. However, their love story was short-lived, and they separated just two years after exchanging vows. Culkin's representative confirmed that the split was amicable and that they remained on good terms. Their divorce was finalized in 2002. During a 2004 interview on "Larry King Live," when questioned about the reason behind his breakup from Miner, Culkin responded, "You know, it just [happens] sometimes. You never want something like that to happen." 

The "Home Alone" star added, "And of course, when we got married, we thought we'd be together forever." Notably, just a few years earlier, when speaking to New York Magazine, Culkin revealed that Miner had broken up with him three times before they eventually got engaged.

The same year that his divorce from Rachel Miner was finalized, Macaulay Culkin began dating "That '70s Show" star Mila Kunis. The "Home Alone" star acknowledged that Kunis' work as the voice of Meg Griffin in "Family Guy" played a key role in sparking their connection, as he was a big fan of the animated series. Throughout their time together, Culkin and Kunis mostly kept their love story under wraps. In a 2007 interview with Parade, she briefly opened up about their relationship, sharing, "We're incredibly private, and I think we relish the privacy we do actually have and are able to sustain it." 

The "Black Swan" star added that she and Culkin enjoyed doing ordinary activities together, like watching movies, cooking, and playing video games. Two years later, she gushed about her man during a chat with Women's Health magazine, noting, "You find a steady rock in your life, and that's all you need." However, in 2011, after nearly a decade together, Kunis and Culkin's relationship came to an end. 

At the time, her representative told Page Six, "The split was amicable, and they remain close friends." Still, the reason behind their separation was left undisclosed. Seven years later, Kunis offered some insight about their breakup on the "Armchair Expert" podcast, taking responsibility for the outcome without delving into details. "It's f***ed up what I did, and it's f***ed up how I did it," she said. 

Following his split from Mila Kunis, Macaulay Culkin took some time before publicly entering the dating scene again. In 2013, the former child star was spotted with his new partner, musician and "All My Children" star Jordan Lane Price. The two were seen hanging out together in Paris, France, during Thanksgiving, with observers pointing to their public displays of affection. "They were very animated and talked together a lot," an onlooker shared with People, adding, "They kissed at the table and were very comfortable."

During this time, Kunis dominated media headlines with her fan-favorite romance with "That '70s Show" co-star Ashton Kutcher, and reportedly, Culkin had a hard time coming to terms with his ex-girlfriend moving on. According to an insider who spoke to the National Enquirer, Culkin was eager to marry Price to prove that he was over Kunis.

The source enthused, "Macaulay is convinced that Jordan's the one for him. They are crazy about each other," (via the Daily Mail). Despite the rumors, Culkin and Price never tied the knot but reportedly remained together until 2017. As the couple kept their relationship low-key, it's unclear when and why they ultimately decided to part ways.

Macaulay Culkin was first romantically linked to Brenda Song, best known for her role as London Tipton in Disney's "The Suite Life of Zack & Cody," in 2017. The two originally met four years earlier, when she was working on the TV series "Dads" and Culkin visited the set, as they disclosed on his podcast, "Bunny Ears." The former child star reminisced about that first meeting, "[Song] totally brushed me off, completely," to which she reasoned, "I was focused." Their paths crossed again while working on "Changeland," a 2019 comedy directed by their mutual friend, Seth Green. 

Despite keeping the beginnings of their relationship otherwise private, Song shared in a 2022 interview with Bustle that she and Culkin spent their first year together traveling. She also praised him in an Esquire interview: "People don't realize how incredibly kind and loyal and sweet and smart he is." The actor added, "He knows who he is, and he's 100 percent okay with that. And that, to me, is an incredibly sexy quality."

The celebrity couple welcomed their first child, a son named Dakota, in 2021. The following year, Culkin proposed to Song, and later in 2022, they welcomed their second son, Carson. In December 2023, after receiving his star on the Hollywood Walk of Fame, Culkin expressed his deep appreciation for Song in his speech, enthusing, "You're not only the best woman I've ever known; you're the best person I've ever known."