Everyone Macaulay Culkin Has Dated, From Mila Kunis to Fiancée Brenda Song

Getty / Kevin Mazur / Kimberly White

Macaulay Culkin has been famous since “Home Alone” came out in 1990, when he was just 10 years old. In the years immediately after, he became perhaps the biggest child star on the 1990s, appearing in movies like “My Girl, “The Pagemaster,” and “Richie Rich.” But by 1995, he had decided to take a break from acting, and he’s tried to keep his life pretty private since. That includes his relationship with fellow actor Brenda Song; the pair reportedly got engaged in January 2022, though they never confirmed that news publicly. And back in 2021, he and Song welcomed their first child, Dakota, named after Culkin’s sister who died in 2008. Their second child, Carson, followed shortly after, and the pair have strived to keep their kids out of the spotlight, too.

Even before he met Song, Culkin has tended to keep his romances low-key, which is pretty understandable, given his lifelong experiences in the spotlight. If you’re curious to at least find out who Culkin dated over the years before he connected with Song, we’ve got answers. His dating history includes a handful of fellow actors, including at least one name you’ll absolutely recognize. Keep reading for a quick rundown of what Culkin has publicly shared about his personal life.

Related: Everything to Know About the Culkin Siblings, Including Macaulay, Kieran, and Rory

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