Macaulay Culkin and Brenda Song have recently celebrated a significant milestone in their relationship. On June 17, the couple marked nine years since they first began dating, an event Culkin reflected on through an emotional Instagram post. The 45-year-old actor shared a sweet message featuring a photograph of them dressed in coordinating pink outfits amidst a picturesque outdoor setting.
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In his heartfelt caption, Culkin expressed how transformative these years have been for him. “Today marks a very special day for me. It’s been 9 years since my life changed forever,” he wrote. He added that for a fifth of his life, he has had the joy of waking up next to Song, stating, “My only regret is that we haven’t had more time together.” Their relationship has flourished since they first met on the set of the film “Changeland,” where they reportedly forged a strong bond.
Culkin and Song, both former child stars, welcomed their first child, Dakota, in April 2021, followed by their second son, Carson, in 2022. The couple’s engagement became public in January 2022, slightly less than a year after the birth of Dakota. In a recent podcast appearance, Song disclosed that Culkin had “kind of re-proposed” to her while she was busy filming “Running Point” in August 2025, adding yet another layer of romance to their story.
Support has poured in for the couple from friends and colleagues within the entertainment industry. Actor Walton Goggins, who starred alongside Culkin in “Fallout,” took to the comments section of the Instagram post to offer his congratulations, calling Culkin a “Good man… wise man,” acknowledging the significance of this milestone in their journey together.
The couple has gradually returned to the public eye over the past couple of years, with both pursuing their acting careers. Brenda Song has appeared in various films since 2025, including “The Last Showgirl,” and is currently starring in the Netflix sports comedy “Running Point” alongside Kate Hudson. Meanwhile, Culkin contributed his voice to a character in “Zootopia 2” and made notable appearances in the second season of “Fallout.” He also featured in two guest roles on “Running Point” across its ongoing seasons.
Their eight-year anniversary, celebrated in June 2025, was marked by a romantic getaway, demonstrating their commitment to nurturing their relationship amid their busy lives. During an appearance on Kylie Kelce’s “Not Gonna Lie” podcast, Song reminisced about the delightful atmosphere Culkin created when he re-proposed to her. Describing the moment, she recalled coming home to find flowers adorning their front door, which swept her off her feet.
In a candid conversation on “Live with Kelly and Mark,” on April 27, Song shared her initial feelings when she first started working with Culkin on the “Changeland” film. Initially thinking of him merely as her best friend, she later realised she may have developed deeper feelings. “I think I have a crush on him,” she revealed, further explaining that it took some time for her emotions to evolve.
“Changeland,” which was both written and directed by Seth Green, has proven to be a pivotal moment in their lives. Song vividly recalled that Green’s wife, Clare Grant, encouraged her to explore a romance with Culkin during filming in Thailand, which led to what she describes as the “longest fling” of her life—now blossomed into a solid partnership with two children.
As Culkin and Song continue to navigate their lives together as partners and parents, their story serves as a testament to the enduring nature of love. Their journey, characterised by friendship, romance, and family, highlights the importance of cherishing meaningful moments throughout both personal and shared experiences.