Brenda Song and Macaulay Culkin’s romance is straight out of a rom-com.
The Disney Channel alum, who got engaged to the Home Alone star in 2022, revealed that their relationship didn’t begin with love at first sight. In fact, their story more closely aligns with the enemies to lovers trope.
“We met through a mutual friend,” Brenda told host Drew Barrymore on a March 10 episode of The Drew Barrymore Show. “The first time we met, I don’t remember meeting him for the first time.”
And though their first interaction didn’t quite spark the flame of their love, the 36-year-old reminisced on the early days of getting to know the fellow child star.
“The first time I actually remember meeting him, the show that I was on with our friend got cancelled,” she explained, “and he was trying to be funny, being like, ‘You know, the show wasn’t that great anyway, you guys are fine.’”
“I did not like him at all,” she admitted, “and he slowly just backed out of the room. He’s like, ‘I’ll just leave.’”
It wasn’t until a few years later that the same mutual friend brought the unlikely duo back together to work on a movie that they wrote, directed and starred in.
The matchmaker in question “basically asked all of his friends to go to Thailand to make this movie, and when we were there, Mac and I we worked a total of, like, 10 days and were there for six weeks and started hanging out,” the Suite Life alum recalled. “I thought he was gonna be my BFF, and then I was like, ‘Oh wait, I kinda have a crush on him.’”
But even with these newfound feelings, Brenda had not suspected that her simple crush would turn into a long-term relationship.
“I thought I was gonna have my first fling,” the Running Point actress quipped, “and that fling has turned into almost eight years and two kids.”
Now, what was once a casual fling has evolved into one of the sweetest couples in Hollywood. And when the “Richie Rich” actor—who shares sons Dakota, 3, and Carson, 2, with the actress—was honored with a star on the Hollywood Walk of Fame in December 2023, he thanked his fiancée with the most heartwarming speech.
“You are absolutely everything,” the 44-year-old said to Brenda in the crowd during his speech. “You’re my champion. You’re the only person happier for me today than I am. You’re not only the best woman I’ve ever know, you’re the best person I’ve ever known.”
“You’ve given me all my purpose,” he continued as he started to choke up. “You’ve given me family.”
For more of a glimpse into Brenda and Macaulay’s adorable romance, keep reading.
Go Rams
Macaulay Culkin and Brenda Song were decked out in their favorite football team’s colors in 2024.
Date Night
The couple stepped out for a rare red carpet date at a Clarins product launch party in Los Angeles in March 2024.
Fun in Cabo
The couple celebrated Brenda’s 36th birthday in Cabo San Lucas, Mexico, in 2024.
Poolside Service
Macaulay purchased a resort tshirt and pretended to be a resort employee, offering Brenda a towel as she lounged poolside.
Bellhop
He also played bellhop and carried her bags, much to Brenda’s confusion and amusement.
Meet Dakota
The two appeared with their son Dakota at Macaulay’s star ceremony on the Hollywood Walk of Fame in December 2023.
Hi Baby
Macaulay and Brenda’s baby boy Carson also made an appearance at the ceremony.
Star Power
The couple were all smiles at the family event.
Trick or Treat
In 2023, the Home Alone star got into the spooky season spirit as Brenda passed out candy.
Black & White Style
The duo appeared at the GFS Fall Benefit in Santa Monica, Calif., in October 2023.
They’re Getting Hitched
In January 2022, a source confirmed to E! News that Brenda and Macaulay were engaged. The actress showed off her engagement ring while stepping out in Beverly Hills.
Heart Day
“Hoppy Valentine’s day everyone!” Brenda shared on Instagram in 2020, when celebrating with Macaulay in the water.
Take Me Away
While strolling through Friedrichshain in Berlin in 2018, the couple displayed some PDA by holding hands.
Proud Parents
In 2022, the couple celebrated their son Dakota’s first birthday with a visit to Sesame Place San Diego. Calling it a “magical” affair, Brenda wrote on her Instagram alongside a snap of herself and Macaulay posing with Elmo, “We had so much fun!”
Birthday Bash
“Happy 40th birthday to this magical being,” Brenda wrote to Macaulay on Instagram in 2020. “I could sit here and write endlessly about how wonderful, kind, loving, genuine, loyal, honest, brilliant and hilarious you are, and how grateful I am that I get to share and do this life thing with you. But firstly, that would take me an eternity and secondly, you won’t even see this because you don’t ever use instagram. Hahaha. My unicorn that I never thought could exist, I am luckiest person in the world because I am loved by you.”
Biggest Cheerleader
“Guys, I did a podcast with my favorite bunny—podcasters and just 2 of my favorite people,” Brenda shared online when supporting her boyfriend’s podcast back in April 2018. “@bunnyearspodcast aaaand the one and only @mattbennett!”
Do-Gooders
Uniting for good! The Hollywood couple attended the 2018 Stand Up To Cancer (SU2C) telecast in Los Angeles.
