Macaulay Culkin’s attempt to re-propose to Brenda Song didn’t exactly go as planned, after he recruited the pair’s sons to help him do it.
The two are proud parents to boys Dakota, 5, and Carson, 4. While Culkin originally proposed to Song with an assist from Dakota around Christmas 2021, he apparently did it again in August 2025, this time hoping to involve both boys in the celebratory moment.
According to Brenda, however, it didn’t go off without a hitch.
Brenda Song Shares Macaulay Culkin Proposal Details
Song opened up about the re-proposal during an appearance on the Not Gonna Lie with Kylie Kelce podcast on April 30, after talking about her love for the Los Angeles Rams.
“This past August, Mac kind of re-proposed to me. It was really sweet,” she recalled. “I was coming home from ‘Running Point,’ and my mom texts me. She’s like, ‘Are you wearing makeup?’ And I was like ‘What?’ They had flowers all by the front door and my two boys.”
“I walk up and I’m like ‘Oh my God’ and he looked at my boys and he goes, ‘Okay what do you say to mama?’” she continued. “And my youngest went, ‘Ram’s House!’”
“He’s so used to me doing callbacks, because I’ll go, ‘Whose house?’ and he’ll go, ‘Ram’s House!’” Song explained, adding, “I’ve trained my kids well.”
She said Culkin told her they “rehearsed and rehearsed” the three of them saying, “Will you marry us?”, but it just wasn’t meant to be. “No, my son instinctively knew, ‘Ram’s house!'” Song added.
Inside Macaulay Culkin’s Initial Proposal
GettyThe “Running Point” actress previously opened up about how Culkin initially popped the question around Christmas 2021, while speaking with The Sunday Times in March 2025.
At the time, they only had Dakota.
“[Culkin] gave me a bunch of really weird presents, like 21 individually wrapped gnomes, which I thought was a joke because we had so many in our garden. Another present was a box of Amazon stuff I said I’d return for him. I was like, ‘I’m not getting this joke.’” she told the outlet.
“Then the last present was a letter written ‘from’ Dakota, like, ‘Papa is such a bad gift-giver, here’s something better to give Mom,’” she shared. “And then he was down on one knee, proposing. He was like, ‘I wanted to lower your expectations.’ Which he did! But it was very sweet and very us. We’re big kids.”
Keeping Their Kids Private
GettyThe pair would welcome son Carson 17 months after Dakota’s birth and have kept the two boys mostly out of the spotlight, aside from an appearance at Culkin’s Hollywood Walk of Fame ceremony in 2023.
“That was such a special moment. We couldn’t have them miss that,” Song told Bustle of the event, before revealing why they prefer for the children to have a low profile.
“Dak was so scared of all the cameras. That’s one of the reasons why we sort of keep them away [from the spotlight]. They did not understand what was happening,” she explained, before sharing another incident that occurred with paparazzi at soccer practice.
“My son was like, ‘Why is that man taking pictures of you, mama?’” Song said. “You could take pictures of me all day. I don’t care. But when it’s your kids, it’s different. They didn’t ask for this life.”
Season 2 of Song’s “Running Point” with Kate Hudson is streaming now on Netflix.
