A Look At Macaulay Culkin's Dating History

Macaulay Culkin may have skyrocketed to fame because of "Home Alone," but the actor is anything but alone. He is happily in love with former Disney star Brenda Song, with whom he shares two children. They have been an item since 2017, and from the looks of it, their relationship is built for the long haul, defying the fleeting nature of Hollywood romances.

But before Culkin got together with "The Suite Life of Zack and Cody" alum, he had quite a tumultuous love life. His romantic past included a failed marriage and an almost decade-long relationship with an A-lister, both of which had been affected by his worldwide fame. Over the years, he's made conscious efforts to maintain a low profile, going through lengths just for a semblance of anonymity. "I'll take walks at two or four in the morning, because there's nobody out on the streets and it's easy for me to go unnoticed," he told Vulture.

Culkin's preference for privacy means that details about his dating history have been largely kept under wraps. But we did a little digging to learn more about his former relationships, including why he decided to get hitched when he was a teenager. Let's dive in!

Macaulay Culkin met his ex-wife, Rachel Miner, at school when he was 14 years old. They had an on-again-off-again relationship until Culkin gave her an ultimatum — either they tie the knot or break things off for good. And as expected from teenagers, they chose the latter. "We dated four times before we got married," he recalled in an interview with New York Magazine. "She'd broken up with me three times before, and so the last time we were going out I said, 'Marry me now before you dump me again.' What can I say? She was my girl."

They tied the knot in 1998 when they were both 17, but predictably, it didn't last long. The pair split just two years later, with a representative for Culkin telling the media that the separation had been amicable. Looking back, the actor recognized that they didn't have a typical marriage, telling CNN's Larry King that it ended because it simply ran its course. "Why doesn't any marriage work," he said. "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."

It didn't take long for Macaulay Culkin to move on after his divorce from Rachel Miner had been finalized in 2002. That same year, he kickstarted a relationship with fellow actor Mila Kunis, which lasted nearly a decade. Funnily, he met the "Black Swan" star at a time when he swore to stay single for a while. "I decided to be abstinent or asexual or whatever. I made a vow, yeah," he told New York Magazine.

Despite having had a relationship that lasted years, their romance was notably lowkey, primarily due to Culkin's widespread fame. "You couldn't walk down the street with him... Fans just screamed when they saw him," Kunis shared in an interview with Howard Stern. But it was fun while it lasted, with the two finding the stability they needed from each other. "We grew up together," she told Women's Health. "You find a steady rock in your life and that's all you need."

The two called it quits in 2011, with a rep for Kunis noting that there was no bad blood between the two. However, she later took accountability for what she described as a "horrible breakup," admitting on the "Armchair Expert" podcast that she could have handled it better. "I was an a**hole in my 20s, and I'll be the first to admit it. And that's something that took me a long time to come out and be like, 'Yeah, you know what, I was a d***k and accept it,' and I own it now," she said.

It wasn't until 2013 that Macaulay Culkin found love again, and at the time, he had been smitten with "All My Children" actor Jordan Lane Price. News of their romance got out when they were spotted canoodling overseas. And at the city of love, no less! "She's a cool chick — based in New York," a source told Us Weekly. "She's into good music (rock) and they hang out in the same parts of New York. They have tons in common."

Not much is known about their relationship — or if it was a relationship at all. But an eyewitness who saw them cozy in Paris told People that sparks were flying when they were together. "They were very animated and talked together a lot," they noted. "They kissed at the table and were very comfortable. They have the air of being very much in love." It's unclear when they broke up and why, but by 2017, Culkin had already been linked to now-fiance Brenda Song.

Fast forward to today, Macaulay Culkin is happily engaged to Brenda Song. They met in 2017 on Seth Green's "Changeland" set and have been together since. Speaking with Esquire, Culkin admitted that their relationship was so good from the get-go that he was expecting it to fizzle out somehow, but they just kept going. Meanwhile, Song had nothing but nice things to say about her soon-to-be husband, telling the outlet: "People don't realize how incredibly kind and loyal and sweet and smart he is. Truly what makes Mack so special is that he is so unapologetically Mack," she gushed. 

The couple welcomed their first child, Dakota (named after his late sister), in 2021, got engaged the following year, and welcomed their second kid, Carson, in 2023. When Culkin received his star on the Hollywood Walk of Fame, he gave Song a shoutout. "You're absolutely everything. You're my champion," he said during his heartwarming speech. "You're the only person happier for me today than I am ... You've given me all my purpose. You've given me family. And after the birth of our two boys, you've become one of my three favorite people."

As for when they'll finally tie the knot? Song said it may take a while since their priority is tending to their kids. "Wedding planning is so expensive and it takes up so much time, she shared with People. "Being a new mom, we're so busy."