From child stardom to parenthood! Though they haven’t always been with each other physically, Macaulay Culkin and Brenda Song have shared some major life experiences together.
The Home Alone actor and the Suite Life of Zack and Cody alum met while costarring in the film Changeland, which was released in 2019. They first sparked romance rumors while the film was in production in September 2017, when they went on a double date at Knott’s Berry Farm in Buena Park, California.
“They were spotted holding hands and being cute with each other,” a source told Us Weekly at the time.
Months later, they made headlines again when they took a trip to Paris with Culkin’s goddaughter, Paris Jackson.
While the pair have kept their relationship relatively private over the last few years, they have opened up about their love for each other in rare interviews.
One year after their relationship became public, the Wendy Wu Homecoming Warrior actress gushed about the former Pizza Underground frontman in a conversation with Us.
“[The relationship is] great!” she said in September 2018. “I don’t like to talk about my personal life, but everything’s wonderful and I’m happy.”
A month earlier, Culkin spoke to Joe Rogan about wanting to start a family with Song during an August 2018 episode of the “Joe Rogan Experience” podcast.
“I’m gonna make some babies,” 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.”
During the interview, the My Girl actor also spoke about his plans to move in with his girlfriend.
“I have a good life out here. I have a pretty little family — a pretty girl, a pretty dog, a pretty cat, and all that stuff. We’re gonna move. We’re doing the house thing and all that kind of stuff,” he said at the time.
Two years later, Culkin opened up again about the pair’s process of getting pregnant.
“We practice a lot,” the Golden Globe nominee told Esquire in February 2020. “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.’”
Just over one year later, Esquire revealed that the couple welcomed their first child, Dakota, on April 5, 2021.
Culkin was previously married to actress Rachel Miner. He also dated Mila Kunis for almost nine years until their split in 2011. Song, for her part, was previously engaged to Miley Cyrus’ older brother Trace Cyrus. They broke up in 2012.
Scroll down to take a look at Culkin and Song’s relationship through the years:
Credit: Marksman/Snorlax/MEGA
Macaulay Culkin and Brenda Song’s Relationship Timeline
From child stardom to parenthood! Though they haven’t always been with each other physically, Macaulay Culkin and Brenda Song have shared some major life experiences together.
The Home Alone actor and the Suite Life of Zack and Cody alum met while costarring in the film Changeland, which was released in 2019. They first sparked romance rumors while the film was in production in September 2017, when they went on a double date at Knott’s Berry Farm in Buena Park, California.
“They were spotted holding hands and being cute with each other,” a source told Us Weekly at the time.
Months later, they made headlines again when they took a trip to Paris with Culkin’s goddaughter, Paris Jackson.
While the pair have kept their relationship relatively private over the last few years, they have opened up about their love for each other in rare interviews.
One year after their relationship became public, the Wendy Wu Homecoming Warrior actress gushed about the former Pizza Underground frontman in a conversation with Us.
“[The relationship is] great!” she said in September 2018. “I don’t like to talk about my personal life, but everything’s wonderful and I’m happy.”
A month earlier, Culkin spoke to Joe Rogan about wanting to start a family with Song during an August 2018 episode of the “Joe Rogan Experience” podcast.
“I’m gonna make some babies,” 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.”
During the interview, the My Girl actor also spoke about his plans to move in with his girlfriend.
[jwplayer ov5RQnup-zhNYySv2]
“I have a good life out here. I have a pretty little family — a pretty girl, a pretty dog, a pretty cat, and all that stuff. We’re gonna move. We’re doing the house thing and all that kind of stuff,” he said at the time.
Two years later, Culkin opened up again about the pair’s process of getting pregnant.
“We practice a lot,” the Golden Globe nominee told Esquire in February 2020. “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.’”
Just over one year later, Esquire revealed that the couple welcomed their first child, Dakota, on April 5, 2021.
Culkin was previously married to actress Rachel Miner. He also dated Mila Kunis for almost nine years until their split in 2011. Song, for her part, was previously engaged to Miley Cyrus’ older brother Trace Cyrus. They broke up in 2012.
Scroll down to take a look at Culkin and Song’s relationship through the years:
Credit: Broadimage/Shutterstock (2)
September 2017
The pair sparked romance rumors when they were spotted holding hands on a date at Knott’s Berry Farm. Culkin and Song were joined by Seth Green and his wife, Clare Grant.
Credit: Broadimage/Shutterstock; MediaPunch/Shutterstock; Richard Shotwell/Invision/AP/Shutterstock
December 2017
The pair spent time with Culkin’s goddaughter, Paris Jackson, while on vacation in France. As they walked through the streets, Culkin kept his arms wrapped sweetly around the former Disney Channel star.
Credit: Chelsea Lauren/Shutterstock
September 2018
Song gushed about her boyfriend in an exclusive interview with Us, noting that while she likes to keep her personal life private, the pair were “wonderful.”
Credit: Matt Baron/Shutterstock
April 2019
The Social Network actress told Entertainment Tonight that she and her boyfriend understand each other because they both grew up in the entertainment industry.
“It’s almost like child actors … don’t even have to talk about it. You just look each other in the eye and you nod and we know,” Song, who got her first film role in 1995, said in an interview published April 29, 2019. Culkin originally entered the public eye when he starred in 1990’s Home Alone.
Credit: Matt Baron/Shutterstock
August 2019
The actor told Joe Rogan that he and his girlfriend were ready to “make some babies” during the August 7, 2021, episode of the “Joe Rogan Experience” podcast.
Credit: Marksman/Snorlax/MEGA
February 2020
Culkin shared that he and Song were officially trying to start a family in an Esquire cover story.
Credit: Courtesy of Brenda Song/Instagram
August 2020
The Suite Life of Zack and Cody alum wished her boyfriend a very happy 40th birthday via Instagram on August 26, 2020.
“Happy 40th birthday to this magical being,” she captioned a photo of the pair wearing matching, personalized pajamas. “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.”
She continued, “My unicorn that I never thought could exist, I am luckiest person in the world because I am loved by you.”
Credit: Jesse Florio
April 2021
The pair revealed to Esquire that they welcomed their first son, Dakota, on April 5, 2021. The healthy baby weighed 6 pounds, 14 ounces and was named after the “Bunny Ears” podcast host’s late sister.
Credit: Matt Baron/Shutterstock; Broadimage/Shutterstock
January 2022
Us confirmed that Culkin and Song were engaged after she was spotted wearing a ring on her left hand during a Beverly Hills outing. “They are and always have been very in love with each other,” a source revealed amid the engagement news.
Credit: Chris Pizzello/Invision/AP/Shutterstock; Matt Baron/Shutterstock
March 2022
“They want more than one kid for sure. … It can definitely happen soon,” a source exclusively told Us, noting that the pair also “definitely want to plan a wedding and get married” within the next couple of years. “They’re committed to each other and are fully in it for the long haul. They’re very in love with each other and have been from the beginning.”
Credit: Shutterstock (2)
April 2022
“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,” Culkin captioned an Instagram photo of him and Song posing with Elmo. “They made a little boy’s dreams come true. And my son also had a great time.”
The Dollface star, who posted the same snap, gushed about the memorable experience, writing, “Thank you sooo much to all the amazing people at Sesame Place San Diego for making BOTH my boys’ dreams come true and for hosting the most magical first birthday for our son! We had so much fun!”