Macaulay Culkin is officially a dad! The former Home Alone star welcomed his first child [1], son Dakota Song Culkin [2], with girlfriend Brenda Song on April 5. The news definitely came as a surprise to some who didn't even know the low-key couple were an item, and that's been the pattern for much of Macaulay's life. It's understandable, given his lifelong experiences in the spotlight, that he'd want to keep his relationships fairly private.
If you're curious to at least find out who Macaulay has dated over the years, we've got answers. His dating history includes a handful of fellow actors, including at least one name you'll absolutely recognise. Keep reading for a quick rundown of what Macaulay has publicly shared about his personal life.
Rachel Miner
In 1998, Macaulay married Rachel Miner, an actress from the soap opera Guiding Light, when they were both 18 years old. A Newsweek article, from when they were just 17 and announcing their plans to marry [3], featured a joint statement from them in which they said they were "thrilled to have found each other as soul mates at such a tender age."
Two years later, the couple separated, and they went on to divorce in 2002. "It is very amicable [4] and they remain [the] best of friends," their spokesperson said, according to ABC News. Rachel has continued acting and is probably best known for her recurring role as Meg on Supernatural.
Mila Kunis
Macaulay's longest-lasting relationship in the spotlight was definitely with Mila Kunis [5], whom he dated from 2002 to 2010. Despite being together for nearly a decade, they remained pretty low-key about it all. Mila was 18 and Macaulay was 21 when they first began dating, staying together through their 20s.
"We grew up together [6]. You find a steady rock in your life and that's all you need. We have our ups and downs, but work through them," Mila told Women's Health in 2009, as reported by People. "I don't know if I met him at 27 if it would have been a different relationship."
In January 2011, news broke that the couple had split some months before. "The split was amicable [7], and they remain close friends," Mila's rep told Page Six at the time. Seven years later, however, Mila admitted that she "f*cked up" the relationship and its ending.
"[It was] a horrible, horrible breakup [8] . . . I f*cked up. I was an ass in my 20s and I'll be the first to admit it," she revealed on Dax Shepard's Armchair Expert podcast.
Jordan Lane Price
Following his breakup with Mila, Macaulay began dating again in 2013, when he went public with singer and actress Jordan Lane Price. People reported that they spent Thanksgiving together in Paris [9] in 2013 and were spotted out together on dates and with friends. Neither commented much on their relationship or on when it ended, but it was apparently over by 2017.
Brenda Song
In 2017, Macaulay filmed the movie Changeland and began dating his costar, Disney Channel star Brenda Song. Entertainment Tonight reported that the new couple were spotted on a double date [10] with Changeland director Seth Green and his wife, Clare Grant.
They've stayed pretty private about their relationship for the most part, although they did both speak to Esquire [11] in 2020. "People don't realise how incredibly kind and loyal and sweet and smart he is," Brenda said, as reported by People. "Truly what makes Mack so special is that he is so unapologetically Mack . . . He knows who he is, and he's 100 percent okay with that. And that to me is an incredibly sexy quality."
The couple also revealed at the time that they were trying for a baby. In April 2021, they announced the birth of their son, Dakota Song Culkin.