Inside Macaulay Culkin and Brenda Song’s Unexpected Love Story

Upon their return to Los Angeles, the first sighting on record of Song and Culkin occurred in July 2017 during the dinner rush at Craig’s in West Hollywood, a celeb-packed haunt where you don’t go if you’re trying to keep a relationship quiet.

They were spotted holding hands on what an eyewitness described as an “affectionate” double date to Knott’s Scary Farm that October with unwitting matchmaker Green and his wife Clare Grant. But Song and Culkin also spent a lot of time in Paris, where he had been living, and hopscotched to Amsterdam, Germany and various locales in the U.S. 

“Spending time traveling, you really get to know someone,” Song told Bustle. “Also, you really get to know yourself, because you start figuring out your strengths and weaknesses and how well you adapt. So we did that for about almost a year.”

And, simply, they’ve been together ever since, not ostentatious with their romance but happily chugging along, joining Green and Grant on a March 2018 day at Disneyland, appearing at Stand Up to Cancer and getting snapped by paparazzi on their coffee runs. (Though Culkin admitted to Esquire in 2020 that he was extremely worried in those early days that it was all too good to be true, that something would occur and blow it up.) 

In addition to having mutual friends, Song and Culkin had both been acting since they were little kids, a shared connection that they didn’t even have to talk about. “You just look each other in the eye, and you nod and we know,” she quipped to Entertainment Tonight ahead of Changeland‘s June 3019 release.

Later that year, Culkin guest-starred on Song’s Hulu series Dollface, a love interest for Shay Mitchell‘s character who Song suspects just might be a serial killer. He’s since been on American Horror Story and The Righteous Gemstones.  

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