Macaulay Culkin and Brenda Song’s Relationship Timeline

Macaulay Culkin and Brenda Song both grew up in the spotlight, and although they didn’t get together until much later in life, their shared child star experience makes their love story that much sweeter.

The couple met in 2017 in Thailand on the set of Seth Green’s movie Changeland. Culkin later admitted to Esquire that when he and Song first started dating, he “was waiting for the other shoe to drop,” though he came to realize, “No—sometimes it’s just good.”

They welcomed a son in 2021 and got engaged less than a year later.

“Macaulay and Brenda have loved being together as a family since welcoming Dakota,” a source told PEOPLE in January 2022. “The engagement is the natural next step for them. They are excited for their future together.”

Brenda Song Says She and Fiancé Macaulay Culkin Are ‘Hands-On’ Parents: ‘We Don’t Have a Nanny’

While talking to Access Hollywood in March 2023, Kieran Culkin confirmed that his brother and Song had quietly welcomed their second child.

From supporting each other’s careers to becoming parents, here is a complete timeline of Macaulay Culkin and Brenda Song’s relationship timeline.

June 2017: Macaulay Culkin and Brenda Song meet on the set of a movie

Brenda Song Instagram

Culkin and Song first met in Thailand on the set of Seth Green’s directorial debut, Changeland.

Green, who also starred alongside the duo in the movie, later told Esquire in 2020 that he was surprised by how much Culkin and Song hit it off. “I didn’t see that one coming,” he admitted.

July 2017: Macaulay Culkin and Brenda Song are spotted together for the first time

The pair were spotted grabbing dinner in Los Angeles and enjoying some quality time together offscreen in July 2017. The outing marked their first public appearance since filming wrapped, and it sparked rumors that the two were more than just costars.

August 22, 2017: Macaulay Culkin appears on Brenda Song’s Instagram

Culkin made his first appearance on Song’s Instagram account in a group selfie. The actor posed next to Song while wearing bunny ears in a picture taken by Green. “Epic first #summerslam ! Shout out to @sethgreen ( aka the king of group selfies ) for this amazing night and epic selfie. Haha,” Song captioned the snap.

October 2017: Macaulay Culkin and Brenda Song enjoy a double date with Seth Green

In the fall of 2017, the pair joined Green and his wife, Clare Grant, for a double date at Knott’s Scary Farm. Culkin and Song were seen holding hands and going on various rides together. “Parkgoers said they were very cute with each other holding hands and very affectionate,” a source revealed to Entertainment Tonight. “Looked like they were having a great time.”

The insider added, “They all looked super comfortable together and like they were having a great night out.”

November 2017: Macaulay Culkin and Brenda Song spend Thanksgiving in Paris

The couple took a romantic trip to Paris for Thanksgiving, where they were spotted enjoying a shopping spree. Culkin was photographed carrying lots of bags while Song cradled a giant teddy bear.

December 2017: Brenda Song spends time with Macaulay Culkin and his goddaughter, Paris Jackson

Brenda Song and Macaulay Culkin.
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During their getaway to Paris, Culkin and Song were spotted out to dinner with the actor’s goddaughter, Paris Jackson, the daughter of Michael Jackson.

January 2018: Brenda Song shows support for Macaulay Culkin’s work

Song supported her boyfriend on Instagram by giving his new podcast, Bunny Ears, a shoutout. She posted a snap of the podcast host wearing bunny ears and captioned it, “Go and check out this stud, @culkamania ‘s new weekly podcast @bunnyearspodcast. It’s a whole lot of amazing.”

April 2018: Brenda Song appears on Macaulay Culkin’s podcast

The former Disney Channel star made an appearance on her beau’s podcast a few months later. Culkin noted on Instagram it was a “groovy episode all about ‘firsts.’ ” Song also posted about the collaboration, and wrote alongside a photo of her and Culkin sporting bunny ears, “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!”

August 2018: Macaulay Culkin talks about wanting to have kids with Brenda Song

While on The Joe Rogan Experience podcast, Culkin opened up about wanting to start a family with Song. “This one’s a good one, so I’m probably going to put some babies in her in a little bit,” he joked. “I mean, we’ve definitely been practicing.”

Macaulay Culkin Says He and Brenda Song Are Trying to Start a Family: ‘We’re Figuring It Out’

He added that he and Song have a great life together. “I have a pretty little family — a pretty girl, a pretty dog, a pretty cat, and all that stuff. We’re gonna move,” he said. “We’re doing the house thing and all that kind of stuff.”

June 3, 2019: Macaulay Culkin and Brenda Song attend the premiere of Changeland

Brenda Song Instagram

Two years after meeting on set, the costars attended the L.A. premiere of their movie, Changeland. Both Song and Culkin hit the red carpet at the ArcLight Hollywood, although they walked it separately and didn’t pose together.

In honor of the movie’s release, Song posted a picture of her and Culkin along with the rest of the cast, calling them her “best friends.”

August 26, 2019: Brenda Song celebrates Macaulay Culkin’s 39th birthday on Instagram

Brenda Song Instagram

Song wished her “favorite human” a happy birthday with a sweet tribute on Instagram. Sharing a photo of balloons that spelled out “Happy B-Day Mack,” The Suite Life On Deck actress wrote, “Happy birthday to my most favorite human @culkamania . Thank you for all that you do. I love you the mostest.”

November 19, 2019: Macaulay Culkin makes a guest appearance on Brenda Song’s show

The couple shared the screen again in an episode of Song’s Hulu show, Dollface. Culkin had a brief cameo in the season one episode titled “History Buff” and played ‘Dan,’ the date of Shay Mitchell’s character.

February 11, 2020: Macaulay Culkin reveals he and Brenda Song are trying to have a baby

In his Esquire cover story, Culkin shared that he and Song were trying to have a baby. “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.’ ”

Song also spoke to Esquire for the story and revealed what she finds attractive about Culkin. “People don’t realize how incredibly kind and loyal and sweet and smart he is,” she said. “Truly what makes Mack so special is that he is so unapologetically Mack.”

She continued, “He knows who he is, and he’s 100 percent okay with that. And that to me is an incredibly sexy quality.”

February 14, 2020: Macaulay Culkin and Brenda Song celebrate Valentine’s Day

Brenda Song Instagram

Song celebrated Valentine’s Day with a silhouette picture of herself and Culkin sporting rabbit ears, a nod to Culkin’s podcast and website. “Hoppy Valentine’s day everyone!🐰❤️” she captioned the photo.

August 26, 2020: Brenda Song celebrates Macaulay Culkin’s 40th birthday on Instagram

Brenda Song Instagram

Song commemorated her boyfriend’s milestone 40th birthday with a heartfelt message on Instagram. “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,” 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. Hahaha. My unicorn that I never thought could exist, I am luckiest person in the world because I am loved by you.”

April 5, 2021: Macaulay Culkin and Brenda Song welcome their first child

The couple became parents in 2021 after they welcomed their first child, son Dakota Song Culkin. While the pair kept the pregnancy private, they shared in a statement that they were “overjoyed” and confirmed that they named their baby after Culkin’s late sister Dakota, who tragically passed away in a car accident in 2008.

November 2021: Macaulay Culkin and Brenda Song enjoy a date night

The new parents enjoyed a date night out at a L.A. Rams game. The couple posed for a picture with the Rams’ mascot, Rampage, and Song captioned it, “Very few things can get us out of the house and away from our son.”

January 2022: Macaulay Culkin and Brenda Song get engaged

Kevin Mazur/Getty

After more than four years of dating, a source told PEOPLE that Culkin and Song were engaged in January 2022. Prior to the news, the actress had been seen sporting a diamond ring on her left hand while out in Beverly Hills, California.

“Macaulay and Brenda have loved being together as a family since welcoming Dakota,” a source told PEOPLE. “The engagement is the natural next step for them. They are excited for their future together.”

January 31, 2022: Brenda Song opens up about parenting with Macaulay Culkin

In an interview for The Cut, Song discussed motherhood and her and Culkin’s “hands-on” parenting style. She also opened up about the difficulties of being a working mother, and said that returning to work just 12 weeks after giving birth to film season two of Dollface was difficult.

“I had no idea what I was doing. I went back to work so early. It was harder than I thought,” Song said. “I pride myself on always being first on set. So to be like, ‘Hey, I need 20 minutes to pump,’ was difficult.”

She continued, “The hours away from my son took a toll on me. Learning my own boundaries while trying to take care of my son and my family — that was hard. But I had a great support system and knew my son was taken care of; I just had FOMO.”

She explained that Culkin’s support and having good communication with each other made it much easier. “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 said. “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: Macaulay Culkin and Brenda Song celebrate their son’s first birthday

The proud mom and dad celebrated their son Dakota’s first birthday at Sesame Place San Diego. Culkin and Song both posted about the day on their respective Instagrams, sharing a photo of themselves with Elmo and Elmo’s dog, Tango. “Just want to send out a BIG thank you to the amazing people over at Sesame Place in San Diego for hosting my son’s first birthday,” Culkin wrote in his caption. “They made a little boy’s dreams come true. And my son also had a great time.”

Song also thanked the staff for “making BOTH my boys’ dreams come true and for hosting the most magical first birthday for our son!” She added, “We had so much fun!”

September 13, 2022: Brenda Song talks wedding planning with Macaulay Culkin

Song opened up to PEOPLE about her upcoming nuptials, saying, “Wedding planning is so expensive and it takes up so much time.” She also pointed out that organizing the event as a parent is “really hard because it’s all about priorities.”

The actress, who launched her own wedding collection with Amazon Handmade, praised the online shop for allowing her to “stop at any time.”

“I don’t feel like I’m having to constantly make an appointment to talk to someone or run to the store,” Song said. “And it’s really hard to do that, not only for new moms out there but for working moms or working dads or those going to school.”

Song added that it’s been “so much fun” to personalize products for the online retailer, including a gold bar bracelet with Culkin’s name on it. “I have one that is similar that I can put my son’s name on it which is really special,” she said.

March 2023: Kieran Culkin confirms that Brenda Song and Macaulay Culkin have welcomed their second child

Culkin’s brother Kieran confirmed the couple’s happy news while chatting with Access Hollywood at the season 4 premiere of Succession in New York City.

“[They] live in Los Angeles and we live in New York. I have a 1-year-old and a 3-year-old, and as busy as I am, there’s just no getting on a plane and going, and same with them,” he said. “I haven’t met No. 2 yet. We just haven’t been able to figure that out.”

December 1, 2023: Brenda Song supports Macaulay Culkin at his Hollywood Walk of Fame ceremony

Amy Sussman/Getty

Culkin, who was joined by Song and their two sons, was honored with a star on the Hollywood Walk of Fame.

Speaking directly to Song during his acceptance speech, the Home Alone alum said: “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 know, you’re the best person I’ve ever known.”

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Source: HIS Education