EXCLUSIVE: Macaulay Culkin 'Pulled It Together' and Began to Come 'Out of His Shell' While Dating Brenda Song
Macaulay Culkin and Brenda Song met in 2014.
Aug. 25 2026, Published 1:46 p.m. ET
Macaulay Culkin said his "life changed forever" after embarking on a relationship with the future mother of his children, Brenda Song.
Ahead of the Home Alone star's 46th birthday on August 26, RadarOnline.com revisits the early days of their romance.
Inside Macaulay Culkin and Brenda Song's Relationship
Macaulay Culkin and Brenda Song didn't spark their romance until 2017.
The would-be couple first crossed paths at Seth Green's home in 2014, shortly after his and Song's sitcom, Dads, was canceled.
Attempting to lighten the mood, Culkin made a poorly timed joke about the situation, but the Suite Life of Zack and Cody star was not having it.
"She was thoroughly unimpressed by me is what I will say," he told Cosmopolitan in January 2025.
Macaulay Culkin and Brenda Song Meet Again in Thailand
Brenda Song said she could tell Macaulay Culkin was 'sensitive' and 'intelligent.'
Three years later, they met again in Thailand on the set of Green's comedy-drama, Changeland.
At the time, Culkin compared his look to Captain Jack Sparrow from Pirates of the Caribbean and admitted to smoking two packs of cigarettes a day.
But Song was curious about the persona he portrayed.
"I saw this person he put out there – it was a product of this armor that he’s put on to protect himself," Song told Cosmopolitan of getting to know Culkin. "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."
Macaulay Culkin Was 'Hiding in Public' Before Meeting Brenda Song
Macaulay Culkin is a former child star famous for 'Home Alone.'
According to a source who spoke with Radar, Culkin's grungy looks over the years were "his way of hiding in public."
"Mac spent years struggling with the fame and attention he got from those Home Alone films at such a young age; he really hated that aspect of the business," added the source.
Song was also not expecting to start a serious relationship, but that's what happened after their 2017 fling turned into something more.
"Brenda’s been coaxing Mac out of his shell, and she’s just what he needs now," the source shared at the time.
Macaulay Culkin Marks 9-Year Anniversary With Brenda Song
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Macaulay Culkin and Brenda Song share two children.
The pair went on to welcome two kids, Dakota and Carson, and got engaged in 2022.
"Macaulay and Brenda have loved being together as a family since welcoming Dakota," an insider revealed to People. "The engagement is the natural next step for them. They are excited for their future together."
Now, nearly 10 years later after sparking their long-term romance, Culkin and Song are still going strong.
This past June, the former child star penned a touching tribute to his partner on their anniversary.
"Today marks a very special day for me. It's been 9 years since my life changed forever," he penned. "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. My only regret is that we haven't had more time together."
