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Macaulay Culkin's high-profile dating history: From Brenda Song engagement to Mila Kunis romance

The Home Alone star has been linked to several famous actresses 

Macaulay Culkin and Brenda Song laughing together
Megan Bull
TV Writer
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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.

Macaulay Culkin and Brenda Song at a 2023 benefit© Getty
Macaulay Culkin and Brenda Song met on the set of Changeland in 2017

Picking 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. 

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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. 

Macaulay Culkin, his fiance Brenda Song and their children stand near his newly unveiled Hollywood Walk of Fame Star © FREDERIC J. BROWN
Macaulay and Brenda with their sons

Speaking 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. 

Macaulay Culkin and Brenda Song attend the ceremony honoring Macaulay Culkin with a Star on the Hollywood Walk of Fame © Amy Sussman
Macaulay honored Brenda in an emotional speech at his Walk of Fame ceremony

Regardless, 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. 

Macaulay Culkin and Mila Kunis at a 2004 event© Getty
Macaulay Culkin and Mila Kunis met in 2002

In 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.

Mila Kunis and Macaulay Culkin at a Hollywood Stars Launch Auction© Getty
Mila stated that she and Macaulay are "not as friendly as we could be," following their breakup

More 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. 

MORE: Minnie Driver's shocking confession about relationship with Matt Damon revealed

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."

Macaulay Culkin & Rachel Miner married in 1998© Steve Granitz
Macaulay Culkin & Rachel Miner married in 1998

Their split was later confirmed by Macaulay's publicist in April 2000. "It is very amicable and they remain best of friends," the statement noted. 

Macaulay Culkin and Rachel Miner on the red carpet© Getty
Their divorce was finalized in 2002

By 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

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