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

On Jan. 26, People reported that Macaulay Culkin and Brenda Song are engaged. The adorable couple, who welcomed their first child back in April 2021, have kept most of their relationship pretty private since they started dating in 2017. But fans occasionally get a glimpse of their romance whenever they post about one another on social media or make a rare joint appearance at public events.

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 after a photographer snapped a pic of them having dinner at Craig's, a popular restaurant in Los Angeles in July.

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, 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, CA. “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.

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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.

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“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.

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“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 powerful.

“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! News 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 who has not had his name revealed, just before Christmas in 2022.

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.

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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’ wedding wearing a new band on her left ring finger.

Culkin and Song were seen with their son, Dakota, in Sherman Oaks on Friday, January 19, enjoying the park together. The couple were wearing adorable matching blue baseball caps, reading “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. Two-year-old Dakota was in a blue shirt printed with dinosaurs, and held his parents' hands as they walked through the grass together.

On Friday, March 15, Macaulay Culkin and Brenda Song made a rare red carpet appearance at the launch party for Clarins' new Multi-Active line. Song wore a strapless sky blue top with oversized 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. The second photo was a picture of a carton of milk that expired the same day—her 36th birthday.

“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.

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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.”

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