Macaulay Culkin and Brenda Song Mark 9 Years

A nine-year milestone with one regret

Macaulay Culkin and Brenda Song are nine years into a relationship that has become both private and, when the moment calls for it, openly sentimental. On June 17, Culkin marked their anniversary on Instagram with a tribute to Song, calling the date “a very special day” and saying it had been “9 years since my life changed forever.”

Culkin, best known to many as the Home Alone alum who grew up under very bright lights, also did a bit of anniversary math. “It’s amazing to think that 1 in every 5 days I’ve been alive I have had the honor of waking up next to the love of my life,” he wrote.

Then came the part that sounded less like a polished celebrity caption and more like someone taking stock. “My only regret is that we haven’t had more time together,” Culkin added. “Thank you for my everything.”

How their relationship began

Culkin, 45, and Song, 38, are parents to two sons: Dakota, 5, and Carson, 3. Culkin and Song have kept most of their relationship out of the Hollywood churn — no small feat for two people who have been famous since childhood.

The pair met in 2013 and later grew close while working together on Seth Green’s 2019 indie film Changeland. Song, a Disney Channel veteran who now stars in Running Point, and Culkin, also known for My Girl, eventually turned that connection into a long-running partnership and family life.

The public reaction to Culkin’s anniversary post was predictably warm. There are worse internet events than people being happy about two former child stars finding steadiness. A low bar, yes, but still worth clearing.

The family re-proposal Song did not see coming

The anniversary tribute was not Culkin’s only romantic gesture in recent memory. In 2025, he involved their two children in a re-proposal to Song, a moment she later described during an April 30 appearance on Kylie Kelce’s Not Gonna Lie podcast.

Song said she had been coming home from Running Point when her mother sent a suspiciously specific text. “She’s like, ‘Are you wearing makeup?’ And I was like ‘What?’” Song recalled.

When she arrived, she found flowers by the front door and her two sons waiting there. Culkin then tried to cue the children for the big moment.

“I walk up and I’m like ‘Oh my God’ and he looked at my boys and he goes, ‘OK what do you say to mama?’” Song said.

Her youngest did answer. Just not with the line Culkin probably had in mind.

“And my youngest went, ‘Ram’s House!’” Song explained, referring to her loyalty to the Los Angeles Rams. “He’s so used to me doing callbacks because I’ll go, ‘Who’s house?’ And he’ll go, ‘Ram’s House!’ I’ve trained my kids well.”

Why the moment landed with fans

The appeal is pretty simple. For fans who watched them grow up on screen, there is something quietly affecting about seeing two former child stars raise children of their own and choose home life over constant performance.

Culkin’s anniversary note did not announce a project, promote a campaign, or tease some grand entertainment industry reveal. It was simply a public thank-you to the person he says changed his life. In celebrity terms, that almost counts as restraint.

Their family moments, from the carefully planned re-proposal to a toddler derailing it with football loyalty, also offer the kind of unvarnished detail that makes famous people seem briefly less managed. For Culkin and Song, nine years together seems to look like gratitude, children, flowers by the door, and one very committed Rams fan under five.