Macaulay Culkin and Brenda Song’s Complete Relationship Timeline

Macaulay Culkin and Brenda Song have shared some major life experiences together. The actors and 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. While Song and Culkin have kept their relationship relatively private over the last few years, they have occasionally opened up about their love. “[The relationship is] great!” Song exclusively told Us Weekly in September 2018. “I don’t like to talk about my personal life, but everything’s wonderful and I’m happy.” Less than three years later, the couple welcomed their first child, son Dakota, in April 2021. Song and Culkin expanded their family the following year when they secretly welcomed their second son, Carson, in December 2022. Scroll down to take a look at Culkin and Song’s relationship through the years:

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.

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.

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.”

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.

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.

Culkin shared that he and Song were officially trying to start a family in an Esquire cover story.

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.”

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.

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.

“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.”

Us broke the news that the couple secretly welcomed their second child, son Carson, sometime before Christmas 2022. 

During Culkin’s Hollywood Walk of Fame ceremony, the Home Alone star gave Song a special shoutout. 

“Lastly, but not least, I’d like to thank Brenda. You’re absolutely everything. You’re my champion,” he gushed of Song, who was in attendance with the couple’s little ones.“You’re the only person happier for me today than I am. You’re not only the best woman I’ve known, you’re the best person I’ve ever known.”

Song pulled back the curtain on her typical date nights with Culkin, telling E! News, "We really don't get out of the house.” When the pair do go out she said, “We eat, we eat and we hang out.”

Song added: “We spend a lot of time together [so] when we have time off, we like to go out and eat."

Culkin was by Song’s side at the premiere of her new movie, The Last Showgirl, at the Toronto International Film Festival. Song stars alongside Pamela Anderson, Jamie Lee Curtis and Kiernan Shipka in the Gia Coppola–directed drama.

Culkin and Song cuddled up courtside at a Los Angeles Lakers game on January 23.

Song marked her eighth anniversary with Culkin in a sweet Instagram post on June 17, 2025. 

“8 years and there is still no one who makes me laugh or smile like the way you do,” she wrote. “No one who makes me feel more seen, heard or loved. My partner in crime, my adventure partner, my best friend, my baby daddy, my favorite everything- thank you. To be loved by you is the greatest privilege. Happy anniversary. I love you.”

On July 28, Song and Culkin showed their love for the Los Angeles Rams when they attended the NFL team's training camp and met with players Jordan Whittington, Steve Avila, Kobie Turner and Jared Verse. 

Culkin revealed Song serenaded him in bed on his 45th birthday, sharing a video of the actress singing Backstreet Boys’ "I'll Never Break Your Heart.” 

“This is 45. Couldn’t appreciate it if I didn’t have it. She makes this whole ‘life’ thing worth it,” Culkin sweetly captioned the clip via Instagram. 

The sentimental moment was all the more special because the pair attended a Backstreet Boys concert together one month prior.