Macaulay Culkin and Brenda Song's Relationship Timeline: From Private Romance to Family of Four

ET is taking a look back at every step of the couple's romance.

Macaulay Culkin and Brenda Song's romance almost seemed predestined, and the pair has done a solid job of developing their relationship outside of the public spotlight.

However, the Home Alone star took the perfect opportunity to publicly introduce his two kids to the world when the actor was honored with a star on the Hollywood Walk of Fame. Culkin and Song's outing on Dec. 1 marked the first time the public got a view of their two children -- son Dakota, 2, and an infant son the couple welcomed in December 2022.

Both stars began their Hollywood careers when they were children, and the shared experience of that kind of life seems to add a sort of kismet to their love story in the minds of fans. Until recently, both Culkin and Song didn't seem to let their private lives get too public.

After the pair began dating several years ago, they cultivated a beautiful family life, welcoming their first child together in 2021 and a second baby just recently. So how did the two stars cross paths and spark a heartwarming bond? ET is taking a look back at the couple's romance journey.

June 2017 - Love on Set

Culkin and Song first met and began to gravitate toward one another while in Thailand, on the set of Seth Green's directorial debut, Changeland. In a lengthy profile on Culkin for Esquire published in February 2020, Green -- who also starred in Changeland, and cast both Song and Culkin for the film -- said he was surprised at how strong and immediate their chemistry was, expressing, "I didn’t see that one coming."

July 2017 -- L.A. Dating

Culkin stepped out with Song at the celebrity hot spot, Craigs, in Los Angeles, on July 24, and they left the popular eatery together. It was the first time the two celebs had been spotted spending time together, thus it was the first time romance rumors had started to swirl. 

September 2017 -- Confirmation

Culkin and Song attended Instagram's Knott's Scary Farm celebrity night on Sept. 29, and a source told ET at the time that the two were very "affectionate" with one another and openly held hands. Culkin and Song were on a double date with Green and his wife, Clare Grant.

Song and Culkin were clearly having fun together riding the amusement park rides, including roller coasters GhostRider and the Silver Bullet. During GhostRider, Song adorably held on to Culkin's arm, making for one memorably sweet snapshot.

November 2017 - City of Love

After just a few months of dating, Culkin and Song went international and the actor treated his girlfriend to a shopping spree at Monoprix in Paris, France. Song shared a snapshot from her trip to the City of Light, which she captioned, "I never want to leave..."

In the caption, she also revealed that she and Culkin were joined on the trip by Green and Grant, as well as Culkin's goddaughter, Paris Jackson.

April 2018 -- Podcasters

After showing support for Culkin's podcast, Bunny Ears, multiple times on Instagram, Song was finally a guest for an episode in April 2018. After recording, Song and Culkin both shared behind-the-scenes snapshots, and celebrated the occasion.

"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!" Song teased. According to Culkin, the episode was "all about 'Firsts.'" Including the first time Song would appear on the show.

August 2018 -- Wanting Babies

Culkin didn't shy away from talking about his relationship with Song during his appearance on an episode of The Joe Rogan Experience podcast, where the notoriously private star said he was very happy with his lady love, and that they had already started considering having kids.

"I'm gonna make some babies," he said when asked by Rogan if he wants kids. "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."

He also joked about having mixed-race children, referencing Sean Lennon, the son of the late John Lennon and Yoko Ono. "This one, I'm going to have some pretty babies," he said. "She's Asian, so I'm gonna have tiny little Asian babies. It's going to be adorable -- a bunch of Sean Lennons running around the house, that's what I'm looking for."

Later, the actor also said he was planning on moving in with Song once she gets her new home, and that he is content and happy in life: "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."

August 2019 - B-Day Bash

Song commemorated Culkin's 39th birthday with some sweet golden balloons that spelled out "Happy B-Day Mack," surrounded by some colorful decorations. She shared a snapshot of the festive balloons to Instagram with a sweet message for her boyfriend. "Happy birthday to my most favorite human," she wrote. "Thank you for all that you do. I love you the mostest."

February 2020 -- Profile Piece

Culkin and Song both opened up in a big way in a profile piece for Esquire that explored Culkin's career and his life. In the interview, the actor opened up about being surprised by how well their relationship worked and he doubled down on comments he previously made about them trying to have a baby.

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"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,'" he quipped. 

Song also gushed about her boyfriend, and explained in the profile, "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. He’s worked really hard to be the person he is."

April 2021 -- New Addition!

After several years of talking about wanting to have kids and "practicing" making babies, the couple quietly welcomed their first child together, a son, in early April 2021. The pair named their son Dakota, in honor of Culkin’s sister, Dakota, who died in 2008.

The baby was born Monday, April 5 at 1:10 p.m. in Los Angeles, weighing 6 pounds, 14 ounces. According to Esquire, who was first to break the news, Song and Culkin were "overjoyed."

January 2022 -- Gettin' Engaged!

In January, Song was spotted out and about in Beverly Hills rocking a massive diamond ring on her finger, revealing that she and Culkin had gotten engaged, nearly a year after welcoming their first child. The following month, during an interview with The Cut, Song confirmed that they were engaged.

"My fiancé and I are very hands-on," she tells the outlet of parenting. "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."

In addition to the help from Song's mom, Mai Song, the Dollface star and Culkin make sure to split up parenting duties as needed.

"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," she says. "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.'"

April 2022 -- 1st Birthday

The adoring parents commemorated Dakota's first birthday with a trip to Sesame Place -- which proved to be a total delight for both their baby and Culkin. Song took to Instagram to share a snapshot and thank those at Sesame Place for the fun outing.

"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!" Song wrote. "We had so much fun!"

September 2022 -- Wedding Planning

Sarah Morris/Getty Images

Song talked about wedding planning while speaking with People and reflected on the challenges she's faced as a working mom raising a toddler and preparing to tie the knot. "Wedding planning is so expensive and it takes up so much time," Song shared. "Being a new mom, we're so busy." She also explained that, when it comes to fitting planning into her schedule, it has been "really hard, because it's all about priorities."

No wedding date has yet been set.

March 2023 -- Baby No. 2

The pair are so good at keeping their personal life out of the spotlight, they apparently welcomed a second child -- and the news did not break until months later. In mid-March, Us Weekly reported the couple's son Carson arrived before Christmas in 2022.  

December 2023 -- The Kids' Public Debut 

Culkin was honored with a star on the Hollywood Walk of Fame, where he and his longtime partner, introduced their two sons to the world in a rare public appearance.

"Lastly, but not leastly, I'd like to thank Brenda," the 43-year-old actor said as he concluded his remarks while giving a speech at the podium. "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," he continued. "You've given me just all my purpose, you've given me family. After the birth of our two boys you've become my three favorite people. I love you so much."

Speaking with ET following the ceremony, Culkin said that having his boys present to witness his big day was "the whole reason to do this."


"It's the reason pretty much to do anything now," he marveled. "We always talk about how we don't remember our life before our kids -- it's a dream or a distant kind of concept, not a reality. I love the fact that my boys can come here and see a dog pee on my name."

For more on the couple, check out the links below.