Brenda Song's First Thoughts On Macaulay Culkin Aren't What You'd Expect

Former Disney Channel star Brenda Song has been up to quite a bit since her time on "The Suite Life of Zack & Cody" ended, including starting a family with longtime beau and 1990s icon Macaulay Culkin, of "Home Alone" fame. The two former child stars became a couple in 2017, and have been engaged since 2022. Along the way, Song and Culkin welcomed two children into the world. Between all this, as well as how often they gush about one another (Song even has a sweet nickname for Culkin), what they have seems to be nothing short of true love, which is why it may be surprising to learn that the "Last Showgirl" star's first impression of her future partner didn't exactly have her hearing wedding bells.

Song and Culkin initially crossed paths back in 2014, having been introduced by mutual friend and fellow actor Seth Green. As they recalled in a joint January 2025 interview with Cosmopolitan, the "Home Alone" star tried to break the ice by making a lighthearted crack or two about "Dads," which co-starred Song and Green, getting the ax after just one season. Needless to say, the joke did not go over well with either of them. The two were already in a bad mood about the whole thing, and apparently glared so many daggers into Culkin that the "Richie Rich" star ended up fleeing the scene entirely. Looking back on that awkward first encounter, Culkin confessed that Song was "thoroughly unimpressed by me."

While no sparks flew during their first meeting, fortunately, Brenda Song and Macaulay Culkin reunited just a few years later, and once again Seth Green was involved. The actor and filmmaker cast the future couple alongside himself in the 2019 film "Changeland," which was notably the "Robot Chicken" co-creator's directorial debut. And, as they confessed to Cosmopolitan, things gradually started getting flirty between them on set. However, the two really connected while discussing hypothetical baby names. 

Song casually mentioned that if she ever had a child, she'd want to name them Dakota (or something similarly gender-neutral). Macaulay, meanwhile, had already planned on naming his own firstborn Dakota after his older sister Dakota Culkin, who tragically died in a car accident in 2008 at just 29 years old. Fast-forward to 2021, when the happy couple welcomed their first son and, true to form, they named him Dakota Song Culkin. That said, getting from point A to point B was still a bit of a personal journey for Macaulay.

During a chat with Esquire that took place shortly after the birth of his first child, Macaulay — whose infamous teenage marriage to Rachel Miner ended in divorce in 2002 — admitted that early in his relationship with Song, the former child star was sort of expecting that something would happen to derail things, despite how well it was going. Fortunately, that moment never came, and his worries subsided. "Sometimes it's just good," the actor, who quietly welcomed another son named Carson Song Culkin in 2022 with Song, noted.