The media caught many of us off guard with the announcement of Macaulay Culkin and Brenda Songs’ first child in 2021.
Suddenly, pictures of the couple were shared on celebrity gossip accounts congratulating them on their first child.
And in March 2023, the couple secretly welcomed their second child, which left many people surprised and asking…
How long have Macaulay Culkin and Brenda Song been together? When and Where did they meet?
There are a lot of unanswered questions about the pairing that I’ll answer here. But before we get to their relationship history, here is a brief bio.
Brenda Song’s Early Life and Career
The young actress is most commonly known for her work with the Disney Channel, specifically as heiress London Tipton in The Suite Life of Zack and Cody from 2005 to 2008 and then The Suite Life on Deck from 2008 to 2011.
Ashley Tisdale played Maddie Fitzpatrick, while Brenda Song starred as London Tipton and Cole Sprouse as Cody Martin in the popular Disney Channel series “The Suite Life of Zack and Cody” and its spin-off “The Suite Life on Deck” (Credit: Disney)
She was born on March 27, 1988, making her 35 years old. Brenda was born in Carmichael, California, and is both Thai and Hmong.
Her grandparents on her father’s side were from the Xiong clan (Hmong) but changed their last name to Song shortly after moving to the United States. Her parents were both born in Thailand but met in Sacramento.
Brenda’s career started at a young age. She and her mother moved to Los Angeles when she was just six years old to further her career.
The then 16-year-old Brenda Song at the premiere of Thunderbirds in Los Angeles on July 24, 2004 (Credit: WENN)
In addition to attending auditions and landing small modeling and acting roles, she took taekwondo classes with her brother and now has a black belt.
She was homeschooled for most of her life (though she got the “high school” experience in her television shows), and attended the University of California, Berkeley, majoring in psychology with a minor in business.
In 2002 Brenda signed her first contract with Disney, starring in the Disney Channel Original Movie Get a Clue. Then in 2005, she joined the cast of The Suite Life of Zack and Cody.
Some Disney cast members struggle to make it in mainstream film and television, but Brenda has done well appearing in The Social Network, New Girl, Dads, and more.
Ashley Tisdale, Brenda Song, and Jennifer Tisdale at the premiere of The Greatest Game Ever Played in Los Angeles on September 25, 2005 (Credit: WENN)
Brenda has kept a pretty low profile. Despite being a young starlet in Hollywood, she has steered clear of the drama and any controversy.
Although in 2008, her picture was used for an escort agency in LA Weekly. This unauthorized use of her photo prompted her to file a libel suit, seeking $100,000 in damages.
Brenda Song dated Miley Cyrus’s brother Trace Cyrus for seven years (Credit: WENN)
Macaulay isn’t the first serious relationship for Brenda. She has been romantically linked to other celebrities, including Miley Cyrus’ brother Trace Cyrus. The two were previously engaged, but she called it off in 2011.
Macaulay Culkin’s Early Life and Career
Everyone seems to know the star as Kevin McCallister from the Home Alone series. An iconic role and film that quickly made the child star the center of attention.
Born on August 28, 1980, he turned 42 in 2022 and was ten years old when he starred in Home Alone.
Macaulay Culkin was 10 years old when he starred in the hit film Home Alone as Kevin McCallister (Credit: 20th Century Studios)
He was born in New York City to a family of performers. His father was an actor on Broadway, and his mother was also an actress. Macaulay had seven siblings, and his brother, Kieran Kyle Culkin, also appeared in Home Alone as his cousin.
Sadly, Macaulay has already lost two of his sisters. His sister Jennifer died of a drug overdose, and his sister Dakota was tragically hit by a car in LA.
His career really peaked in the late 80s and early 90s. In addition to Home Alone, he appeared in films such as Uncle Buck, My Girl, Michael Jackson’s “Black or White” music video, and Richie Rich.
In 1994 he said he wanted to retire from acting, seeking a more normal life. He did temporarily take a hiatus from action. However, he has returned to the big screen several times since in films such as Saved! and Party Monster.
In 2013 he started a parody rock band called The Pizza Underground, which split up in 2016. He has appeared in periodic television and radio commercials ever since.
Macaulay Culkin shows off his teeth while taking a selfie at the LA Premiere of Gravitas Ventures’ “Changeland” at ArcLight Hollywood on June 3, 2019, in Hollywood, California (Credit: WENN)
Back in 2004, many assumed Macaulay was going down the path many child actors do – drug use. He was arrested for possession of marijuana, Xanax, and Klonopin.
In 2018, he legally changed his name to Macaulay Macaulay Culkin Culkin following a vote on his website, and now goes by his middle name “Macaulay Culkin.”
Mila Kunis and Macauley Culkin dated for 8 years until breaking up at the beginning of 2011 (Credit: WENN)
Brenda Song isn’t the first celebrity relationship for Macaulay. He was married to actress Rachel Miner and was in a long-term relationship with Mila Kunis, whom he dated from 2002 until 2011. They lived together and, despite breaking up, remained friends.
Rachel Miner and Macaulay Culkin married in 1998 and divorced in 2002 (Credit: WENN)
Macaulay Culkin and Brenda Song: Relationship History
Although many people just heard about the pairing with the announcement of their child, the two have actually been together for a few years. Here are all the details on how they met and the relationship milestones they’ve hit over the past few years.
The two first met in July when they co-starred in Seth Green’s movie Changeland. They began dating shortly after the meeting, which was a surprise to Green – “I didn’t see that one coming,” he told Esquire.
Clare Grant and Brenda Song at the LA Premiere of Gravitas Ventures’ “Changeland” at ArcLight Hollywood on June 3, 2019, in Hollywood, California (Credit: WENN)
Although they didn’t initially come out publicly, fans were speculating the two were romantically involved as they were photographed getting dinner together in LA in July.
“I was waiting for the other shoe to drop,” Macaulay confessed to Esquire regarding his early days of dating Song, but he eventually understood that “No – sometimes it’s just good.”
Macaulay’s first appearance on Brenda’s Instagram account was in August 2017, where the actor was seen posing with bunny ears next to Brenda in a group selfie taken by Green.
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Brenda captioned the picture, “Epic first #summerslam ! Shout out to @sethgreen ( aka the king of group selfies ) for this amazing night and epic selfie. Haha.”
Brenda told Entertainment Tonight that they bonded over the shared experience of being child actors, “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.”
Later in October, Brenda and Macaulay went on a double date with Seth Green and his wife, Clare Grant. They then took their relationship to the next level when they traveled to France along with Paris Jackson, who happens to be Macaulay’s goddaughter.
In January 2018, Brenda endorsed Macaulay’s new podcast, Bunny Ears, on Instagram, showing her support for his work. She shared a photo of the podcast host wearing bunny ears and captioned it with, “Go and check out this stud, @culkamania’s new weekly podcast @bunnyearspodcast. It’s a whole lot of amazing.”
Later in April, Brenda made an appearance on Macaulay’s podcast, where they discussed their “firsts.” Macaulay mentioned on Instagram that it was a “groovy episode.”
Brenda also shared the collaboration on her Instagram, posting a photo of herself and Macaulay wearing bunny ears and writing, “Guys, I did a podcast with my favorite bunny-podcasters and just 2 of my favorite people @bunnyearspodcast aaaand the one and only @mattbennett! Check it out and let me know what you think!”
In August 2018, Macaulay Culkin appeared as a guest star on the popular podcast The Joe Rogan Experience. During this interview, he revealed a lot about the relationship, though with some controversial remarks.
When asked about the relationship, he said, “This one’s a good one, so I’m probably going to put some babies in her in a little bit. I mean, we’ve definitely been practicing.”
Macaulay Culkin was 10 years old when he played Thomas J. Sennett in the 1991 coming-of-age comedy-drama film My Girl (Credit: Columbia Pictures)
He went on to say, “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,”
Macaulay expressed that he and Brenda share a wonderful life together, stating, “I have a pretty little family – a pretty girl, a pretty dog, a pretty cat, and all that stuff. We’re gonna move,” he continued, “We’re doing the house thing and all that kind of stuff.”
In September, Brenda shared similar sentiments, although in a much subtler way. She spoke with US Weekly and said, “I don’t like to talk about my personal life, but everything’s wonderful, and I’m happy.”
The costars, who had met on set two years prior, attended the L.A. premiere of their movie Changeland in June 2019. Although they walked the red carpet separately and didn’t pose together, they were both present at the ArcLight Hollywood.
Brenda celebrated the release of the film by posting a photo of her and Macaulay, along with the rest of the cast on Instagram, referring to them as her “best friends.”
The cat-loving duo was spotted together on June 19, 2019, at CatCon in Pasadena, California, and looked as happy as ever. The event must have had a lasting impact on them because Macaulay gifted Brenda a cat named Santa Claws for Christmas.
Brenda Song shows off her feet in high heels on the red carpet (Credit: WENN)
She posted a picture of the cat on Instagram with the caption, “Introducing the newest member of our family…Santa Claws!!!”
In August 2019, Brenda took to Instagram to wish Macaulay a happy 39th birthday. She posted a photo of balloons spelling out “Happy B-Day Mack” and wrote a heartfelt tribute to her “favorite human,” thanking him for all that he does and expressing her love for him.
Later in November, the couple once again shared the screen in an episode of Brenda’s Hulu show, Dollface. Macaulay made a brief appearance in the first season episode called “History Buff,” playing the character ‘Dan,’ who is the date of Shay Mitchell’s character.
Although they haven’t been one of those celebrity couples that consistently express their love and devotion on social media, Brenda did give a heartfelt shout-out for Macaulay’s 40th birthday.
The caption appeared under a cute photo of the couple wearing matching flannel pajamas. Below she wrote, “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.” She concluded, “My unicorn that I never thought could exist, I am the luckiest person in the world because I am loved by you.”
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In February, starting a family seemed to be top of mind. Macaulay spoke to Esquire again and said, “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.”
In the same story, it was revealed that Brenda keeps a special notebook by their bed where she writes down “Mack’s” funny one-liners.
Brenda shared, “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. He knows who he is, and he’s 100 percent okay with that. And that to me is an incredibly sexy quality.”
Very few knew what the couple was expecting. The two welcomed a baby boy at 1:10 pm in Los Angeles on April 5, 2021. Weighing just 6 pounds, 14 ounces, the little one was named after Macaulay’s late sister Dakota who died in 2008 after being hit by a car.
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The new parents had a date night out at an L.A. Rams game in November 2021. They took a picture with the Rams’ mascot, Rampage, and Brenda captioned it with, “Very few things can get us out of the house and away from our son.”
After being together for over four years, Macaulay and Brenda got engaged in January 2022. Before the announcement, the actress was spotted wearing a diamond ring on her left hand while out in Beverly Hills, California.
A source told People, “Macaulay and Brenda have loved being together as a family since welcoming Dakota. The engagement is the natural next step for them. They are excited for their future together.”
In a January 2022 interview with The Cut, Brenda shared details about her and Macaulay’s parenting style and the challenges of being a working mother. The actress revealed that returning to work after just 12 weeks of giving birth to film season two of Dollface was tough, as she had to balance her work and motherhood responsibilities.
Brenda said, “I had no idea what I was doing. I went back to work so early. It was harder than I thought. I pride myself on always being first on set. So to be like, ‘Hey, I need 20 minutes to pump,’ was difficult.”
She added, “The hours away from my son took a toll on me. Learning my own boundaries while trying to take care of my son and my family — that was hard. But I had a great support system and knew my son was taken care of; I just had FOMO.”
Brenda emphasized the importance of open communication and Macaulay’s support, saying, “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.'”
In April 2022, Macaulay and Brenda celebrated their son Dakota’s first birthday at Sesame Place San Diego. The couple shared their gratitude on their Instagram accounts, posting a photo of themselves with Elmo and his dog, Tango.
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Macaulay expressed his appreciation for the staff, writing, “Just want to send out a BIG thank you to the amazing people over at Sesame Place in San Diego for hosting my son’s first birthday. They made a little boy’s dreams come true, and my son also had a great time.”
In September, Brenda talked to People to share wedding planning tips, saying, “Wedding planning is so expensive and it takes up so much time,” and pointed out that organizing the event as a parent is “really hard because it’s all about priorities.”
Brenda, who launched her own wedding collection with Amazon Handmade, said she appreciated the online shop for allowing her to “stop at any time.”
She said, “I don’t feel like I’m having to constantly make an appointment to talk to someone or run to the store. And it’s really hard to do that, not only for new moms out there but for working moms or working dads or those going to school.”
Brenda expressed that customizing items for the online shop have been “so much fun” for her, such as creating a gold bar bracelet with Macaulay’s name on it.
She shared, “I have one that is similar that I can put my son’s name on it which is really special.”
In March 2023, Kieran Culkin confirmed to Access Hollywood at the season 4 premiere of Succession in New York City that Brenda Song and Macaulay Culkin have welcomed their second child.
Kieran said, “[They] live in Los Angeles and we live in New York. I have a 1-year-old and a 3-year-old, and as busy as I am, there’s just no getting on a plane and going, and same with them.
He added, “I haven’t met No. 2 yet. We just haven’t been able to figure that out.”
In January 2013, Brenda Song looked super chic while out and about in Los Angeles.
The then 25-year-old actress and model headed to Edible Arrangements, probably to get some fresh fruits and chocolates. Perhaps all the sweets were for her then-boyfriend Trace Cyrus?
We know Brenda Song is a chic dresser, and this outfit sums up everything we love about her fashion sense!
Wearing skinny distressed jeans, Brenda Song stopped by Edible Arrangements in Los Angeles on May 11, 2013 (Credit: WENN)
She loves to keep things simple, yet sassy and interesting at the same time. The actress, singer, film producer, and model wore a plain white tank top paired with distressed skinny jeans.
To complete the look, she carried a Chanel handbag and sported a pair of brown platform sandals.
Brenda Song shows off her size 6 (US) feet in high heels (Credit: WENN)