Macaulay Culkin and Brenda Song recently made a rare public appearance together, with the “Home Alone” star calling his fiancée “the best person I’ve ever known.”
The two stars, who have been romantically linked since 2017, are famously low-key about their relationship. However, the couple stepped out together — and debuted their two sons — when Culkin received a star on the Hollywood Walk of Fame in December.
Here’s a complete timeline of Culkin and Song’s relationship.
June 2017: Culkin and Song met on the set of the 2019 movie ‘Changeland’
Macaulay Culkin and Brenda Song in “Changeland.” Gravitas Ventures
The film was written and directed by Seth Green, who also starred alongside the pair in the movie. Song and Culkin’s relationship was a surprise to fans and Green, who told Esquire in 2020, “I didn’t see that one coming.”
Years after they started dating, Culkin told Esquire that at the onset of the relationship, he was waiting for the other shoe to drop because it felt too good to be true.
“And it’s always gonna drop,” he said. “Something bad’s gonna happen. Someone’s gonna die!”
July 2017: The two stars were linked after being photographed in public together
On the left: Macaulay Culkin at New York Comic Con in October 2017. On the right: Brenda Song at a Knott’s Scary Farm event in September 2017. Jason Kempin/Getty Images for Adult Swim; Barry King/Getty Images
Dating speculation began in summer 2017 when paparazzi snapped photos of them getting dinner at Craig’s in Los Angeles, California.
According to Us Weekly, Culkin and Song later went on a double date with Green and his wife Clare Grant on Friday, September 29. The group reportedly spent time at Knott’s Berry Farm in Buena Park, California.
Then in December 2017, they were seen in France with Paris Jackson, Culkin’s goddaughter.
Song said that she, Culkin, and their ‘Changeland’ costars bonded over being child stars
Macaulay Culkin and Brenda Song both started their acting careers at young ages. 20th Century Fox; Disney Channel
“Child actors, we don’t even get to talk about it, you just look each other in the eye and you nod and we know,” Song told Entertainment Tonight in April 2019 of working with Culkin, Green, and Breckin Meyer.
Culkin’s acting career began as a child in the 80s. He rose to fame after starring as Kevin in “Home Alone,” the hit family film that resulted in a sequel that he also starred in and a franchise led by other actors.
Meanwhile, Song gained prominence thanks to roles in Disney Channel films and shows. She starred in three of the network’s original movies called “Get a Clue,” “Stuck in the Suburbs,” and “Wendy Wu: Homecoming Warrior” in addition to landing a role on the sitcom “Phil of the Future.”
Song is perhaps best recognized for playing a spoiled heiress named London Tipton on Disney Channel’s “The Suite Life of Zack and Cody,” which starred Dylan Sprouse, Cole Sprouse, and Ashley Tisdale.
August 2018: Culkin said that he was ‘practicing’ starting a family with Song
Brenda Song and Macaulay Culkin in September 2018. Kevin Mazur/Getty Images for Stand Up To Cancer
“This one’s a good one, so I’m probably going to put some babies in her in a little bit,” Culkin said during an interview for a podcast called “The Joe Rogan Experience,” released in August 2018.
“I mean, we’ve definitely been practicing,” he said.
“I’m going to have some pretty babies. She’s Asian, so I’m gonna have tiny little Asian babies. It’s going to be adorable — a bunch of Sean Lennon’s running around the house, that’s what I’m looking for,” Culkin added, referring to the son of John Lennon and Yoko Ono.
Culkin also said they were planning on moving into a house together.
September 7, 2018: Song described her relationship with Culkin as ‘great’
“I don’t like to talk about my personal life, but everything’s wonderful and I’m happy,” she told Us Weekly while in attendance at a Stand Up To Cancer event in Santa Monica, California.
June 29, 2019: They attended CatCon together in Pasadena, California
Brenda Song and Macaulay Culkin at CatCon at on June 29, 2019 in Pasadena, California. Sarah Morris/Getty Images
They met up with a few other cat-lovers at the event, like Song’s “Dollface” costar Kat Dennings and “The Office” alum Angela Kinsey.
December 25, 2019: Culkin got Song a cat named Santa Claws
Song posted photos of their cat on Instagram with the caption: “Introducing the newest member of our family… Santa Claws!!! #bestchristmaspresentever.”
As of April 2021, they have two other cats named Apples and Dude, a Shiba Inu named Panda, some fish, and a blue-headed pionus (a kind of parrot), per Esquire.
August 26, 2020: Song shared a heartfelt post for Culkin’s 40th birthday, calling him a ‘magical being’
“Happy 40th birthday to this magical being,” the “Social Network” star captioned a photo of the couple wearing matching flannel pajamas with their names written on the back.
She continued: “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.”
“My unicorn that I never thought could exist, I am luckiest person in the world because I am loved by you,” Song concluded.
February 2020: In a cover story for Esquire, Culkin again spoke about his desire to be a parent
Brenda Song and Macaulay Culkin in September 2018. Kevin Mazur/Getty Images for Stand Up To Cancer
“We practice a lot,” he told the publication. “We’re figuring it out, making the timing work. Because nothing turns you on more than when your lady comes into the room and says, ‘Honey, I’m ovulating.’”
Elsewhere in the article, Song gushed about Culkin and said, “people don’t realize how incredibly kind and loyal and sweet and smart he is.”
“Truly what makes Mack so special is that he is so unapologetically Mack,” she continued. “He knows who he is, and he’s 100 percent okay with that. And that to me is an incredibly sexy quality. He’s worked really hard to be the person he is.”
Additionally, Song spoke about Culkin’s hardships and said that “he is the actor he is now because of all the things he had to go through.”
At the time of the article’s publication, the two stars had moved into their home together with their pets.
According to the cover story, the “Dollface” star also keeps a customized notebook near her bed, which she fills with Culkin’s humorous one-liners.
April 5, 2021: The couple welcomed a son together named Dakota Song Culkin
Macaulay Culkin and Brenda Song in September 2018. Kevin Mazur/Getty Images for Stand Up To Cancer
Culkin and Song shared the news with Esquire magazine that month with the statement: “We’re overjoyed.”
Baby Dakota was born at 1:10 p.m. in Los Angeles, weighing 6 pounds and 14 ounces, the publication reported. The couple’s newborn was named after Culkin’s sister who died in 2008 after being struck by a car in Los Angeles.
The news came as a surprise to fans, who either didn’t know they were in a relationship or were unaware that they were expecting a child.
January 26, 2022: People and E! News reported that Culkin and Song got engaged
People was the first to report the engagement, followed by E! News. Both publications cited an anonymous source.
The reports emerged the day after Song was photographed wearing a ring with a large gemstone on her left ring finger while in Beverly Hills.
Representatives for Culkin and Song didn’t immediately respond to Insider’s requests for comment.
January 2022: Song spoke about her and Culkin’s ‘hands-on’ parenting approach in an interview with The Cut
“My boyfriend and I are very hands-on,” she told the publication. “We don’t have a nanny, but my mom has been here with us since my son was born. He’s 9 months old now. When I was working, my mom would bring him to set so I could breastfeed and see him during the day.”
Song added: “I think when you and your partner have kids, especially the first few months, you don’t have the patience to be polite with each other. Being communicative when you need help is so important. Instead of having set duties, we just feel each other out. I’ll be putting my son down and my partner is like, ‘Let me feed the animals and get dinner ready.’”
March 2023: The couple welcomed their second child
Outlets including People reported that Culkin and Song quietly welcomed a second son in March 2023. Culkin’s brother, Kieran, confirmed the news to Access Hollywood during an interview.
“I haven’t met No. 2 yet, and they haven’t met No. 2 yet either,” Kieran said, referring to his wife and children. “We just haven’t been able to figure that out.”
December 1, 2023: Culkin got emotional while thanking Song for her support during his Hollywood Walk of Fame ceremony
Macaulay Culkin, Brenda Song, and their oldest son at the Hollywood Walk of Fame on December 1, 2023. Variety/Getty Images
Culkin was surrounded by family and friends when he received a star on the Hollywood Walk of Fame on December 1, including Song, their two sons, Quinn Culkin, Rory Culkin, “Home Alone” costar Catherine O’Hara, Natasha Lyonne, Seth Green, and Paris Jackson.
Culkin became a household name as a child for films like “Home Alone,” “My Girl,” and “Richie Rich.” He’s recently starred in TV series like “American Horror Story: Double Feature” and “The Righteous Gemstones.”
He praised Song in his acceptance speech, calling her the “best woman” he’s ever known.
“I’d like to thank Brenda,” Culkin said in a clip shared by Pop Crave. “You are absolutely everything. 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 known, you’re the best person I’ve ever known.”
“You’ve given me all my purpose. You’ve given me a family, and after the birth of our two boys, you’ve become one of my three favorite people,” he added. “You’re somewhere in there. But I love you. I love you so much.”
Macaulay Culkin and his youngest son at the Hollywood Walk of Fame on December 1, 2023. Variety/Getty Images
Culkin concluded his speech by quoting his “Home Alone” character, Kevin McCallister.
“To wrap things up, in the spirit of the holiday season, I just want to say, Merry Christmas, ya filthy animals,” he said.
In an Instagram post shared after the event, Culkin said that his sons “can’t stop playing” with his star.
“It was such a special day to spend with my friends and family,” he wrote in his caption.
Song also praised Culkin in her own Instagram post, writing: “So sooo proud of you @culkamania !! The most incredible day honoring the most incredible person. So well deserved and so long overdue. Thank you so much to everyone who came out to support and celebrate. My heart is so full.”
