Macaulay Culkin's Dating History Includes Several Fellow Hollywood Stars

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, 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 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.

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 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 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.