Brenda Song and Macaulay Culkin: What to Know About Their Relationship

Former child stars Macauley Culkin and Brenda Song welcomed their first child together last week, but many fans are still catching up on their relationship. Culkin and Song got together in 2017, and have quietly started a family with some fans never noticing. Now, the couple is more than happy to open up for curious fans.

Culkin and Song announced the birth of their son, Dakota on Monday in an interview with Esquire. The baby boy was reportedly born on Monday, April 5. That announcement has fans looking back on updates they missed — from the pregnancy announcement to the meet-cute or even the existence of the relationship itself. Thankfully, as big stars, Culkin and Song’s relationship is relatively well-documented.

Culkin is best known for starring in the Home Alone franchise as a child but has gone on to big projects in nearly every form of media since then. Today, he hosts a podcast called Bunny Ears and runs a satirical website under that name as well.

Meanwhile, Song is best-known as a Disney Channel star of the early-2000s, from movies like Wendy Wu: Homecoming Warrior and Stuck in the Suburbs to TV shows like Phil of the Future and The Suite Life of Zack & Cody. Song successfully broke out the Disney machine and transitioned into more adult roles, including shows like New Girl and Dollface, and movies like The Social Network.

Together, this undeniable power couple has now casually taken over the world of celebrity gossip coverage for the week. Here’s a look at Culkin and Song’s relationship over the last four years.

June 2017 – ‘Changeland’

Culkin and Song reportedly first met while filming Changeland together in June of 2017. The dramedy is written and directed by Seth Green, who also starred in it. Green spoke to Esquire about Culkin and Song’s relationship and how it all started there, saying: “I didn’t see that one coming.”

Although it was filmed in 2017, Changeland did not come out until the summer of 2019. It is now available for rental or purchase on most digital stores, and it is streaming with a subscription to the services Hoopla and Kanopy. However, fans looking for Culkin and Song’s meet-cute in the movie might be disappointed.

July 2017 – Rumors

Rumors of a real-life romance between Culkin and Song first went public a month later, when they were seen getting a nice dinner together in Los Angeles, California. At the time, Us Weekly published paparazzi shots of the duo together and a few more throughout the summer. They went on a double date to a theme park with Green and his wife in September, then they were spotted in France that December, hanging out with Culkin’s goddaughter Paris Jackson.

August 2018 – Family

Culkin spoke out publicly about his relationship with Song in August of 2018 when he appeared on The Joe Rogan Experience podcast, though he didn’t reveal her identity. Even then, he hinted that things were very serious and likely to be permanent. 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.”

“I’m going to have some pretty babies. She’s Asian, so I’m gonna have tiny little Asian babies,” Culkin went on. “It’s going to be adorable — a bunch of Sean Lennon’s running around the house, that’s what I’m looking for.”

The actor also revealed in this interview that he and Song were in the process of moving in together. Meanwhile, a few weeks later Song spoke to Us Weekly at a charity event. When asked about Culkin, she said: “I don’t like to talk about my personal life, but everything’s wonderful and I’m happy.”

April 2019 – Child Stars

Song gave a major hint about what brought her and Culkin together in April of 2019 during an interview with Entertainment Tonight. She said that the two of them — as well as Green and Breckin Meyer — bonded easily on the set of Changeland because of their pasts as child stars.

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,” she said.

June 2019 – Cat People

Culkin and Song’s next major public appearance together came in June of 2019 at “CatCon” — a convention for cat-lovers in Pasadena, California. They posed for photos with other stars including Song’s Dollface co-star Kat Dennings and The Office alum Angela Kinsey.

December 2019 – Christmas

Just a few months later, Song posted a photo of a new cat on Instagram, describing it as “the newest member of our family.” Fans couldn’t help but notice the phrasing and leap to conclusions about Song and Culkin’s private life. The couple has three cats — Apples, Dude and Santa Claws — as well as a Shiba Inu named Panda.

February 2020 – Fatherhood

Just over a year ago, Culkin confirmed that he and Song were trying to have a baby in an interview with Esquire. He said: “We practice a lot. 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.’”

Here, it was no secret that Culkin and Song were dating, and Song contributed to the profile as well. She told the interviewer that “people don’t realize how incredibly kind and loyal and sweet and smart he is,” adding: “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. He’s worked really hard to be the person he is.”

August 2020 – Birthday Wishes

Song broke her rule about sharing her personal life in August of 2020 on Culkin’s 40th birthday. In a heartfelt post, she wrote: “Happy 40th birthday to this magical being. 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. 

April 2021 – Dakota

Song reportedly gave birth to baby Dakota at 1:10 p.m. on Monday, April 5 in Los Angeles, California. The baby weighed 6 pounds, 14 ounces and was deemed healthy. He was named after Culkin’s late sister, who passed away in 2008 in a car accident. The new parents told Esquire they are “overjoyed” to have Dakota. Judging by the commentary online, fans are happy too.