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.

“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: