Macaulay Culkin regrets not spending more time with Brenda Song in their relationship.
Nine-Year Tribute
The couple marked nine years together on Wednesday, June 17th. The 45-year-old actor took to Instagram and paid a sweet tribute to the 38-year-old actress.
Macaulay posted a shot of the pair all dressed up as they posed in an idyllic garden. He wrote, “Today marks a very special day for me. It’s been 9 years since my life changed forever.”
“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. Thank you for my everything.”
2025 Re-Proposal
The Home Alone star popped the question in 2022. It was less than a year after he and Running Point‘s Brenda welcomed their son, Dakota, five, into the world.
But when it came to the couple’s sweet re-proposal in August 2025, it was their other boy, Carson, three, who accidentally stole the attention.
Appearing on an episode of Kylie Kelce’s Not Gonna Lie podcast earlier this year, Brenda shared the story. She explained, “So this past August, Mack kind of re-proposed to me, and it was really sweet.”
“I was coming home from Running Point, and my mom texted me. She was like, ‘Are you wearing makeup?’ And I was like, ‘What?!'”
“He had flowers all by the front door, and my two boys, and I walk up, and I was like, ‘Oh my God.'”
“He looked at my boys and said, ‘OK, what do you say to Mama?’ And my youngest went, ‘Rams’ house!’ Because he’s so used to me doing callbacks. He’s used to me doing, ‘Who’s house?’ ‘Rams’ house!’ I’ve trained my kids well.”
“Mack was like, ‘We rehearsed, and we rehearsed, Will you marry us?’ But no, my son knew, Rams’ house [family’s chant for the Los Angeles Rams].”
First Meeting
Macaulay and Brenda met in 2014 at 52-year-old actor Seth Green’s home.
In January 2025, Brenda expressed to Cosmopolitan that she did not like Macaulay’s joke about the cancellation of her and Seth’s show, Dads.
She recalled, “He was trying to be funny about our show being canceled, and I was not having it.”
Macaulay added, “She was thoroughly unimpressed by me, is what I will say.”
But it was not until Macaulay and Brenda reunited on the Thailand-based set of Seth’s 2019 comedy-drama Changeland that they hit it off.
In 2020, Macaulay admitted to Esquire that he “didn’t see that one coming.”