Brenda Song & Macaulay Culkin's Relationship Is Full Of Green Flags

Every few years, there is that one celebrity couple that is universally shipped and we find ourselves unable to get enough of them. This is most definitely true for Brenda Song and Macaulay Culkin, the couple that was never on our bingo cards, but we have some to find out that we needed them. According to a timeline by ELLE Magazine, the pair began dating in 2017 and kept their relationship mostly private. However, they would speak about each other publicly on several occasions.

In 2021, the pair welcomed their son Dakota Song Culkin and several months later, a source told People that the new parents were engaged. In 2023, they welcomed their second son Carson Song Culkin. And the two have been gushing about each other in the media, including videos they did with Cosmopolitan that had us gushing. Plus their social media posts have us swooning, including an Instagram post Culkin shared for Song's birthday in March 2025 where he wrote that he called her an "amazing woman."

[Embed: https://www.instagram.com/p/DHusxhZxtek/]

We could go on and on about how much we love the former child stars, which we will do because Brenda and Macaulay's relationship is nothing but green flags!

We all know that Macaulay Culkin and Brenda Song were child stars, which includes extensive comedic backgrounds. Every holiday season, we cannot help cracking up as Culkin portrayed Kevin McCallister, and we can quote Song's London Tipton in every situation. So, it is natural that the couple are their own comedy duo. 

A video of them on the red carpet at the Vanity Fair Oscar Party in March 2025 showed Culkin posing hilariously while Song was busy looking beautiful for the camera. When she turned around and saw what he was doing, they laughed and walked away from the photographers.

[Embed: https://www.tiktok.com/@vanityfair/video/7477472483348630814?lang=en]

"When London Tipton meets Richie Rich," one commenter said. "She brings out his inner child, he feels safe," another person said. In January, the couple appeared on the cover of Cosmopolitan Magazine and quickly stole fans' hearts. They even played a cute quiz game to see how well they knew each other's roles, and their laughter was contagious.

One of the most important things a partner can do is be supportive and Macaulay Culkin and Brenda Song seem very versed in this principle. One of the best examples was in December 2023 when Culkin received his star on the Hollywood Walk of Fame. Song was in the front row cheering on her man with their two kids Dakota and Carson Song Culkin. 

Speaking at the podium, Culkin said, "Brenda, you are absolutely everything. You're my champion, 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. You've given me all my purpose. You've given me family." 

Most of us were tearing up along with Song and this sweet moment not only introduced that Culkin and Song were an item, but also a family. And we began to wonder how we existed without them.

Most of us are not "put together" every day, and it means a lot when our partners love us whether we are made up or made down. During an interview with People in March 2024, Brenda Song praised Macaulay Culkin for doing just that. Song said Culking makes her feel beautiful when she is makeup-free.

"I think he's the one that really made me feel the most beautiful when I'm about to go to bed and I have nothing on my face and I'm so tired," she told the publication. "We're about to watch some really silly thing on TV, and he looks at me, and [I'm like], 'He makes me feel so confident.' I have someone who makes me feel beautiful without a stitch of makeup on."

Well, we cannot blame Culkin because Song is a natural beauty, and it is so sweet that he is not afraid to boost her confidence.

Any time you begin a new relationship it can be a scary, especially if you have your walls up. During their cover interview with Cosmopolitan in January 2025, Brenda Song noted that she and Macaulay Culkin had been hurt in past relationships, which made them keep their expectations low. But as their romance slowly began to blossom, Culkin had given Song some of his personal journals to read, which allowed her to have a glimpse of who he was behind "this armor."

"I'd never felt this way before," he said admitting that he fell in love with her first, "I believed in her. I mean, I believed in people before, but I believed in her down to my bone marrow." (Who is cutting onions in here?) Similarly with Song, Culkin was the first boyfriend she brought home to her parents and she told People that he was the first actor she had ever dated.

Song also noted to Cosmo that being an Asian American actress created this need to constantly hustle and be "very proactive," but added that Culkin helps her "chill out," while she helps "bring out that [fire] in you." We are beyond happy for the beautiful couple and grateful that they are allowing us to get a glimpse into their magical love story!