Macaulay Culkin & Brenda Song Finally Reveal How They Started Dating

Macaulay Culkin and Brenda Song are one of those celebrity couples you might forget are an item, and that’s just the way they like it. The super-private lovebirds gave some rare comments about their relationship in a Jan. 27 Cosmopolitan profile, revealing that they have made conscious efforts to not be very public with their romance. “That the public is like, ‘Wait, they’re together and they have kids?’ Good. That means we did our job,” Culkin said.

Although they’ve kept specific details about how they met, started dating, and started their family together close to the vest for nearly a decade, Culkin and Song finally told their love story to Cosmo, detailing how they actually didn’t hit it off at all the first time they met one another.

2014: Macaulay Makes A Bad First Impression

The two actors were introduced by mutual friend Seth Green. They met at Green’s house, but things didn’t go well when Culkin started cracking jokes about Song and Green’s sitcom Dads getting recently canceled.

“He was trying to be funny about our show being canceled and I was not having it,” Song recalled. Culkin picked up on the tension: “She was thoroughly unimpressed by me is what I will say.”

2017: They Reconnected On A Movie Set

Three years after that disaster, Green brought the two together again, this time by casting the pair in his directorial debut, Changeland. While filming in Thailand, Culkin and Song formed an unlikely bond, although they still kept things platonic.

“I saw this person he put out there — it was a product of this armor that he’s put on to protect himself,” Song said of getting to know Culkin during this time. “But I could see that that wasn’t really who he was; I could see these glimpses of this really interesting, very sensitive, very intelligent, artistic person that he doesn’t really let show.”

2021: They Welcomed Their First Son

After realizing their feelings for one another, Culkin and Song got busy starting their family. On April 5, 2021, Song gave birth to their firstborn. They named him Dakota, both because Song had previously mentioned liking the gender-neutral name, and in honor of Culkin’s late sister with the same name.

2022: They Got Engaged & Had Another Son

At the beginning of 2022, Culkin popped the question in a unique way, gifting Song 21 garden gnomes before asking her to be his fiancée. Later that year, they had their second son, whom they named Carson.

Although Culkin and Song have been engaged for several years now, they’re not in a hurry to walk down the aisle. “We talked about eloping,” Song said in January 2025. “But I was like, ‘If we eloped, my mom would have a heart attack that she wasn’t going to be there.”