Macaulay Culkin and Brenda Song sparked marriage rumors during the Home Alone star's Walk of Fame ceremony in December. Supported by his fiancée and their two sons, the A-lister fuelled further speculation over his marital status, after Brenda flashed a decadent gold band on the red carpet.
Macaulay and Brenda are yet to address the rumors, but it's clear that they're blissfully in love, following their 2017 meet-cute. But, did you know that the Home Alone star has been married before, and to Supernatural actress Rachel Miner? We're taking a look at Macaulay's high-profile dating history, which also includes an eight-year relationship with Mila Kunis. Keep reading for all the details…
Brenda Song
Fellow child stars Macaulay Culkin and Brenda Song grew up in the spotlight, but it wasn't until 2017 that they finally crossed paths. After jetting to Thailand to film Seth Green's directorial debut, Changeland, the duo hit it off straight away.
© GettyPicking up where they left off, Macaulay and Brenda reunited in Los Angeles, where they were often spotted grabbing dinner. By October of that year, the couple's romance was confirmed after they were photographed holding hands at Knott's Scary Farm.
An extremely private couple, Brenda gave a brief update on their relationship in 2018. Speaking to US Weekly, she said: "I don't like to talk about my personal life, but everything's wonderful and I'm happy." She also appeared on Macaulay's Bunny Ears podcast that year.
While Macaulay and Brenda rarely speak about their private life in interviews, they have posted about one another on social media, not to mention their two sons.
In a 2020 interview with Esquire, Macaulay, 43, first confirmed that he and Brenda were trying for a baby. Their oldest son, Dakota, was eventually born on April 5, 2021, and by March 2023, Macaulay's brother, Kieran, confirmed that they'd welcomed a second son.
© FREDERIC J. BROWNSpeaking to The Cut about parenting with Macaulay, in 2022, Brenda said: "Being communicative when you need help is so important. Instead of having set duties, we just feel each other out. I'll be putting my son down and my partner is like, 'Let me feed the animals and get dinner ready.'"
As for their engagement, Macaulay popped the question in 2022, and whether or not the couple have since tied the knot, remains to be seen.
© Amy SussmanRegardless, Macaulay's heartfelt speech at his Walk of Fame ceremony shone a light on the depth of their love for one another. "You are absolutely everything. You're my champion. You're the only person happier for me today than I am. You're not only the best woman I've ever known, you're the best person I've ever known," he said.
Mila Kunis
After meeting in 2002, Mila Kunis and Macaulay Culkin dated for eight years. During their relationship, the actors were spotted attending various press events, after-parties and Hollywood charity events together.
© GettyIn a rare 2007 interview with Parade, Mila spoke about their relationship, telling the publication: "We're incredibly private, and I think we relish the privacy we do actually have and are able to sustain it. We enjoy each other's company. We like to read books, play video games, watch TV, or go to the movies. And he's an amazing cook. He makes dinner every night."
By early 2011, however, Mila and Macaulay had ended their relationship. "The split was amicable, and they remain close friends," the actress's publicist told the New York Post.
© GettyMore recently, Mila – now married to Ashton Kutcher – was asked about her relationship with the Kevin McCallister actor. During a 2018 appearance on Dax Shephard's Armchair Expert podcast, she said: "I was an [expletive] in my 20s, and I'll be the first to admit it. It's [expletive] up what I did, and it's [expletive] up how I did it."
Mila also confirmed that she and Macaulay are "probably not as friendly as we could be," following their breakup. She made the confession while appearing on the WTF with Marc Maron podcast.
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READ: All the best declarations of love from iconic couples
Rachel Miner
Macaulay Culkin and Alice actress Rachel Miner tied the knot at the age of 18. Prior to their wedding, the couple confirmed their intention to marry in a joint public statement, saying that they were "thrilled to have found each other as soul mates at such a tender age."
© Steve GranitzTheir split was later confirmed by Macaulay's publicist in April 2000. "It is very amicable and they remain best of friends," the statement noted.
© GettyBy 2002, Rachel and Macaulay's divorce was finalized. Rachel has since gone on to star as Meg in Supernatural, and she's also landed roles in Sons of Anarchy, Criminal Minds and Chicago Fire.
