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Macaulay Culkin has managed to keep his love life out of the public eye despite dating a few famous women. Since his relationship history is short and sweet, the former child star doesn’t have a long list of ex-girlfriends or wives. However, he was once married when he was 18 years old. Just a few years after he rose to fame from his successful holiday film, Home Alone, Macaulay married Supernatural actress Rachel Miner in 1998. At the time, the former lovebirds said in a joint statement that they were "thrilled to have found each other as soul mates at such a tender age,” per Newsweek. However, the pair ended up divorcing in 2002, with a spokesperson telling ABC News at the time, "It is very amicable, and they remain [the] best of friends.” Later that year, the Home Alone 2: Lost in New York star began dating Mila Kunis. The duo were going strong for several years, as the That ‘70s Show alum gushed about the success behind their relationship in an August 2009 interview with Women’s Health. “I don’t know if I met him at 27 if it would have been a different relationship,” Mila told the publication at the time. “We grew up together. You find a steady rock in your life, and that’s all you need. We have our ups and downs but work through them.” Nevertheless, the couple split by 2010, and the Luckiest Girl Alive actress admitted during a 2018 appearance on the “Armchair Expert” podcast that she and Macaulay had a “horrible breakup.” "I f—ked up, I was an a—hole in my 20s,” she confessed without detailing what exactly went down between the two. “It's f—ked up what I did, and it's f—ked how I did it.” Despite Macaulay’s past heartbreak, he eventually found the love of his life in current fiancée, former Disney Channel star Brenda Song. The couple got engaged by early 2022 and later welcomed two sons — Dakota and Carson — in 2021 and late 2022, respectively. While Brenda and Macaulay tend to keep their relationship on the down-low, the former Suite Life of Zack & Cody star gushed about her love in an August 2020 Instagram post. “I could sit here and write endlessly about how wonderful, kind, loving, genuine, loyal, honest, brilliant and hilarious you are, and how grateful I am that I get to share and do this life thing with you,” she wrote at the time. “But firstly, that would take me an eternity, and secondly, you won’t even see this because you don’t ever use Instagram. Hahaha. My unicorn that I never thought could exist, I am [the] luckiest person in the world because I am loved by you.” Scroll through the gallery to see all of Macaulay’s former relationships.