A Complete Timeline of Brenda Song and Macaulay Culkin’s Relationship

On Jan. 26, 2022, People reported that Macaulay Culkin and Brenda Song were engaged. The couple, who welcomed their first child in April 2021 and second in March 2023, have kept most of their relationship private since they started dating in 2017.

Still, they post about each other on social media on occasion and have attended events together. In January 2025, they even had a rare date night at Lakers game.

Here, we trace the actors’ under-the-radar love story.

Macaulay Culkin and Brenda Song starred in the movie Changeland, written and directed by Seth Green. Rumors started circulating that they were dating in July 2017 after a photographer snapped a pic of them having dinner at Craig’s, a popular restaurant in Los Angeles.

In late September, they were seen out at Knott’s Berry farm with their former director and his wife, Clare Grant. Song and Culkin were spotted holding hands.

In 2020, Green talked to Esquire about discovering Song and Culkin’s relationship, saying, “I didn’t see that one coming.”

In that same interview, Culkin said that his relationship with Song was going so well in those early days that he was always waiting for the “other shoe to drop.”

“And it's always gonna drop,” he said. “Something bad’s gonna happen. Someone’s gonna die!”

The couple traveled to France and were seen with model Paris Jackson, Michael Jackson's daughter and Culkin’s goddaughter.

In an interview on The Joe Rogan Experience podcast, Culkin jokes about “practicing” making a baby with Song.

“This one’s a good one, so I’m probably going to put some babies in her in a little bit,” he said. “I mean, we’ve definitely been practicing.”

He added, “I’m going to have some pretty babies. 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.” (He was referring to John Lennon and Yoko Ono’s son.)

“It’s great!” she told Us Weekly at the Stand Up to Cancer event in Santa Monica, California. “I don’t like to talk about my personal life, but everything’s wonderful, and I’m happy.”

Song said she bonded with Culkin, Green, and co-star Breckin Meyer on the set of Changeland over being former child stars. Song is best known for her role on The Suite Life of Zack & Cody, but she was in a number of Disney shows and movies throughout her childhood as well. She told Entertainment Tonight that this brought her closer to Culkin.

“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.

The duo went to visit some famous cats at CatCon in Pasadena with their famous friends, including Song’s Dollface co-star Kat Dennings and Angela Kinsey of The Office.

On Instagram, Song made her own cat famous, introducing their new pet “Santa Claws,” a Christmas gift from Culkin. They have a number of pets, according to Esquire, including two more cats, a parrot, several fish, and a Shiba Inu.

“Happy 40th birthday to this magical being,” Song wrote in a glowing caption for Culkin, sharing a photo of them wearing matching PJs with their names on the back.

“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,” she wrote. “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 spoke to Esquire for a profile about her beau’s life and career. She told the magazine, “People don’t realize how incredibly kind and loyal and sweet and smart he is.”

She added, “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.”

In the story, Culkin brought up the idea of “practicing” for kids again.

“We practice a lot,” he said. “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.’”

On April 5, 2021, Culkin and Song announced the birth of their first child, a son named Dakota. Their statement on the matter was brief but poignant.

“We’re overjoyed,” they said.

The baby was reportedly named after Culkin’s sister who died in 2008 when she was hit by a car in Los Angeles. The couple had kept Song’s pregnancy under wraps, and fans were surprised by the news.

People and then E! both cited anonymous sources on Jan. 26, 2022 who said Song and Culkin were officially engaged. Song had been photographed wearing what looked like an engagement ring while walking through Beverly Hills.

On Friday, March 17, 2023, Song and Culkin confirmed they secretly welcomed a second child, another son just before Christmas in 2022. Song revealed his name was Carson in a January 2025 Bustle interview.

Song posted an uncaptioned photo on November 1, showing herself in a witch hat and costume looking through the door at her husband, who is wearing what looks like a clown costume.

On Friday, December 1, Culkin thanked Song at his Hollywood Walk of Fame ceremony in Los Angeles.

“You are absolutely everything,” the actor said, getting visibly emotional. “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 know, you’re the best person I’ve ever known.”

Song wiped a tear from her eye as he continued, saying, “You’ve given me all my purpose. You’ve given me family. After the birth of our two boys, you’ve become one of my three favorite people.”

Song later sparked marriage rumors when she was photographed at Kat Dennings’s wedding wearing a new band on her left ring finger.

Culkin and Song were seen with their oldest son, Dakota, in Sherman Oaks on Friday, January 19, enjoying the park together. The couple were wearing matching blue baseball caps that read “PAPA” and “MAMA.”

Culkin had on a red T-shirt with a Sesame Street print and a pair of black sweatpants. Song wore a striped shirt under a dark-blue jacket and sweatpants.

On Friday, March 15, Culkin and Song made a rare red carpet appearance at the launch party for Clarins’s new Multi-Active line. Song wore a strapless sky-blue top with oversize denim pants with an extra long hem that just revealed the tip of her black heels. Culkin was in a classic black blazer with black jeans and a T-shirt. He was wearing glasses and Converse sneakers in black-and-white.

The Clarins event was reportedly held at a private residence in Los Angeles and was attended by Christina Aquilera, who also performed.

On Wednesday, March 27, Culkin shared picture of Song sitting in a robe with a towel on her head, with a bottle of champagne on the table in front of her. It was his birthday tribute.

“Happy birthday to the best friend, mother, ally, colleague, lover, and partner I could ever wish for. You are my reason. I love you. P. S. The milk is due. Can you pick some up on your way home from work?” Culkin wrote in the caption.

Culkin detailed the playful way they spent Song’s big day: a vacation with running gag throughout it. “So the lady and I went to @nobuloscabos for her birthday,” he started. “On our first day we went to the gift shop and I found this shirt. Since now I looked like the staff I decided to spend my four days there masquerading as a: Poolside waiter, housekeeper, cabana boy, room service attendant, bell hop. Thanks again @nobuloscabos for the fun time and excellent stay. And thanks for selling that shirt. It really made me feel like I belonged.”

On October 19, the couple made a splash on the red carpet at the fourth annual Academy Museum Gala in Los Angeles. Culkin wore a classic black tux, and Song was in a gold gown with an asymmetrical neckline and long cape. They stopped to flirt in front of the cameras.

In an interview with E!, Culkin shared one of the most important aspects to his relationship with Song.

“Brenda and I are very good at communicating with each other,” he explained. “We have no secrets. We’re constantly on the line—we talk, we talk.”

He added that they can often see how the other is feeling without words, especially when managing their children.

“I call it tagging in and out,” he said. “You know, ‘You tag in.’ Like wrestling. ‘Hey, I’ve been at us for about three hours. I need to tag out. I need quiet time.’ We call it quiet time. ‘I need to go upstairs and have quiet time.’”

He added that he can tell when Song has “hit her wall.”

“We just talk, that’s the best way to do it,” he continued. “We‘re in the thick of it, 2-year-old and 3-year-old...God bless, Brenda is a champion. And she is the best mom. She’s the best boy mom. She’s just the best mom. She’s the best person. I wake up every day knowing I’m lucky. Not feeling I feel lucky, but I know I’m lucky.”

They also enjoyed a “magical” trip to “end and start the year.” Song shared a carousel of photos from what looks like a tropical getaway. In one pic, Culkin can be seen leaning into the image, which revealed their bedroom and blazing fireplace.

Song and Culkin got to take in a special evening together. On January 23, they were photographed attending the Lakers’ game against the Celtics.

On February 18, actress, writer, and producer Mindy Kaling received a star on the Hollywood Walk of Fame, and the couple attended in a show of support.

In a March 1 interview with The Times of London, Song shared details of how Culkin asked her to marry him.

“He gave me a bunch of really weird presents, like, 21 individually wrapped gnomes, which I thought was a joke because we had so many in our garden,” Song recalled. “Another present was a box of Amazon stuff I said I’d return for him. I was like, ‘I’m not getting this joke.’”

She added, “Then the last present was a letter written ‘from’ [our son] Dakota, like, ‘Papa is such a bad gift-giver, here’s something better to give Mom.’ And then he was down on one knee, proposing. He was like, ‘I wanted to lower your expectations.’ Which he did! But it was very sweet and very us. We’re big kids.”

The actress also shared more about what drew them together and their dynamic now.

“He’s good at lifting me up on a down day,” Song explained. “My favorite treat will just show up, or flowers that say ‘just because’ or he’ll turn down the monitor [and get up with the kids] so I sleep in. I’ve never had someone tell me how much they appreciate me.”

She continued, “When we met neither of us were looking for a relationship. We had loads of downtime just hanging out and I was like, ‘Is he going to be my set BFF? Awesome!’ And then I got a crush on him and I was like, ‘Is he going to be my first fling?’ When we flew back to L.A. I literally said, ‘See you never!’ But that fling somehow turned into eight years and two kids together.”

Song said they never fight.

“What’s the point?” she asked. “Yelling won’t get my point across any better, and he feels the same way. Once the kids are in bed, that’s our time together and we talk.”

The couple was seen in New Orleans to take in the Kansas City Chiefs playing the Philadelphia Eagles.

The pair wore matching off-white ensembles to the Vanity Fair Oscars After-Party.

Song and Culkin were photographed with matching jerseys at the Los Angeles Lakers and the Minnesota Timberwolves at Crypto.com Arena game on April 22 in Los Angeles.

On June 18, Song and Culkin celebrated their eight-year anniversary with two posts on Instagram to commemorate the occasion. Song shared two photos, one seemingly from the beginning of their relationship and the second from now. In the first pic, they’re at a table dressed in white tablecloths and red settings, each wearing bunny ears and leaning into one another. In the second photo, they’re smiling goofily at the camera, again appearing to be at a restaurant.

In the caption, Song wrote, “8 years and there is still no one who makes me laugh or smile like the way you do. 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❤️”

Culkin’s post is also a carousel, but every photo is of Song as she moves towards his camera on the beach. The actress is wearing all-black, including a black bikini, black net coverup skirt and top, and black wide-brimmed hat with black sunglasses. In one hand she’s carrying a her black flip-flops and she has a black handbag over her shoulder. She is smiling broadly.

In the caption, Culkin wrote, “Happy anniversary, babe. Thank you for always coming towards me. You never run away.”

They shared pictures from their anniversary trip on June 19.