As a couple, Macaulay Culkin and Brenda Song stand out for their charm and genuine connection, which is not always seen in Hollywood. Their journey from co-stars to lovers has been one marked by rumors, public appearances, and, ultimately, the joyous announcement of parenthood. As fans of Culkin’s iconic role in the Home Alone franchise and Song’s diverse contributions to film and television, audiences have followed the couple’s evolving relationship with keen interest. Let’s take a look at the timeline of their relationship.
Early 2017: Brenda Song & Macaulay Culkin Meet On Set
The paths of the Home Alone star and the former Disney Channel actress first crossed in Thailand. Specifically, during the filming of the movie, Changeland. Moreover, Seth Green, the film's writer and director, candidly shared with Esquire his surprise at how well the two stars connected. He confessed that he "didn't see that one coming.”
Whispers of romantic involvement between Culkin and Song began to circulate in July 2017 when they were photographed together in Los Angeles. The two seemed to be enjoying each other’s company while they grabbed dinner. Furthermore, the rumor gained significant traction when Song shared a group photo featuring Culkin on her Instagram account. Soon after, they were spotted holding hands during what appeared to be a double date with Seth Green and his wife.
December 2017: A Parisian Getaway
By the end of 2017, fans were assured that Brenda Song and Macaulay Culkin were an item. In December, the couple were spotted on a romantic vacation in Paris. They were photographed walking together, hand-in-hand, as they wandered through the famous capital. The headlines continued when they were also seen having dinner with Culkin’s goddaughter, Paris Jackson.
2018: Adoration & Confirmation
In January 2018, Song took to her Instagram to shout out her boyfriend’s new podcast, Bunny Ears. Posting a photo of Culkin wearing bunny ears, she captioned it: “Go and check out this stud, @culkamania‘s new weekly podcast @bunnyearspodcast. It’s a whole lot of amazing.” A few months later, she appeared on said podcast with Culkin, Matt Bennett, and Matt Cohen. By August, Macaulay Culkin was featured on The Joe Rogan Experience, where he spoke about wanting to start a family with Song. “This one's a good one,” he said. “So I'm probably going to put some babies in her in a little bit.”
2019: Keeping Things Private
Macaulay Culkin and Brenda Song have maintained a relatively private relationship. However, they share occasional glimpses into their personal life through social media. In 2019, they attended multiple events together, constantly supporting each other's projects. In June, the couple attended the L.A. premiere of Changeland, and Song posted a picture with Culkin and the rest of the cast. A few months later, Song wished Culkin a happy 39th birthday via Instagram. Additionally, in the adorable post, she referred to him as her “most favorite human.”
2020-2021: Macaulay Culkin & Brenda Song Start A Family
Right before Valentine's Day, 2020, Culkin revealed in his Esquire cover story that he and Song were trying hard to have a baby. “We practice a lot. We're figuring it out, making the timing work,” he said. That year, the pair celebrated Valentine’s Day together, shouting each other out on social media.
Fast forward to April 2021, and Culkin and Song became parents. The couple announced the birth of their first child—a son named Dakota Song Culkin. They kept the details about their pregnancy relatively low-key, choosing to share the news a week after their son was born. Even after they became parents, the couple found ways to relish some time alone and on dates.
2022: The Road To “I Do”
With the joy of the new year came the news that Macaulay Culkin and Brenda Song had got engaged. A source told People that “Macaulay and Brenda have loved being together as a family since welcoming Dakota. The engagement is the natural next step for them. They are excited for their future together."
In September, Brenda Song spoke to People about her and Culkin planning their nuptial. “Wedding planning is so expensive and it takes up so much time,” she said. “Being a new mom, we're so busy. It feels so convenient to be able to sit down and be able to get everything done all at once.”
2023: Baby Number Two & A Hollywood Star!
Culkin and Song welcomed their second child in March, naming the baby boy Carson. Nine months later, Song and their two sons joined Culkin as he received a star on the Hollywood Walk Of Fame. While giving his speech, the actor teared up as he showered Song with beautiful words. “You are absolutely everything. You're my champion,” he said. The actor continued by referring to Song as “not only the best woman I've ever known, you're the best person I've ever known.”