Honestly, if you told a Disney Channel fan in 2005 that London Tipton would end up with the kid from Home Alone, they probably would’ve laughed you out of the room. It sounds like fan fiction. But here we are in 2026, and the Brenda Song relationship with Macaulay Culkin isn't just a tabloid headline—it’s arguably one of the most stable, low-key success stories in Hollywood.
They’ve been together for nearly nine years now. Most people didn't even know they were a "thing" until they already had a toddler and a massive diamond ring in the picture. That’s the trick, isn't it? In an era where every influencer relationship is curated for the algorithm, Song and Culkin basically went underground. They built a life instead of a brand.
How it Actually Started (It Wasn’t Love at First Sight)
Forget the "spark" stories you see in rom-coms. When Brenda Song and Macaulay Culkin first met in 2014 at mutual friend Seth Green’s house, it was kind of a disaster. Mack (as his friends call him) was trying to be funny. He started cracking jokes about Brenda’s sitcom Dads getting canceled.
She wasn't laughing.
She recently told Cosmopolitan that she was "thoroughly unimpressed" by him at first. He was just this guy making fun of her job. It took three more years and a trip to Thailand to change that. They both got cast in Seth Green’s directorial debut, Changeland, in 2017. Being stuck in a foreign country for seven weeks has a way of stripping away the Hollywood ego. They bonded over the one thing very few people on earth understand: growing up in front of a camera.
The Secret Life of Brenda Song and Macaulay Culkin
By the time the public realized they were dating, they were already deep in it. They started popping up at NBA games and making the occasional appearance on each other’s Instagrams, but they never "sold" their romance.
Then came 2021.
On April 5, 2021, they welcomed their first son, Dakota Song Culkin. They named him after Mack’s sister, who tragically passed away years ago. It was a heavy, beautiful tribute. They kept the pregnancy so quiet that when the news broke, the internet basically collectively gasped.
That 2021 Christmas Proposal
The proposal was peak "them." Mack didn't hire a flash mob or a private jet. Instead, he leaned into their shared weirdness. He gifted Brenda 21 individually wrapped garden gnomes.
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Why? Because they already had a ton in their garden and he wanted to "lower her expectations" before the real gift. The final present was a letter "written" by baby Dakota (who was only 7 months old at the time) basically saying, "Papa is a bad gift-giver, here is something better."
Then he hit the knee with a ring that experts estimate is worth between $400,000 and $600,000. Not bad for a guy who started the day with garden gnomes.
Growing the Family in Total Secrecy
In late 2022, they did it again. They welcomed their second son, Carson Song Culkin. Most of the world didn't even know Brenda was pregnant until Mack’s brother, Kieran Culkin, accidentally confirmed it to the press months later.
They don't have nannies. That's a huge deal for two people who could easily afford a small army of help. They’ve been vocal about being hands-on. Brenda has talked about the "FOMO" she felt going back to work on projects like Running Point, but she credits their "support system" and Mack’s parenting for keeping her sane.
It’s a partnership. They alternate "on-duty" times. While one is filming, the other is on "stocking duty" for Christmas or managing the chaos of two toddlers.
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What Most People Get Wrong About Brenda's Past
Before the stability of the Brenda Song relationship with Culkin, things were... chaotic. Specifically the Trace Cyrus era.
If you remember the early 2010s, Brenda was in a very public, very volatile on-and-off relationship with Miley Cyrus’s brother. They were engaged in 2011, then they weren't. They were together, then they weren't.
Even as recently as 2025, Trace was still airing grievances on Instagram, making wild, unverified claims about their time together. Brenda has never publicly engaged with the drama. She just moved on. It’s a stark contrast to the quiet, protective bubble she’s built with Culkin.
Why They Still Haven't Married (Officially)
As of early 2026, they are still "engaged." They’ve talked about eloping, but Brenda is pretty sure her mom would have a "heart attack" if she wasn't there to see it.
They seem to be in no rush. When you already have a home, two kids, and a decade of history, a piece of paper starts to feel like a formality. Culkin famously said during his Hollywood Walk of Fame ceremony in 2023, "You are absolutely everything. You're my champion. You're the only person happier for me today than I am."
Actionable Insights for Fans and Observers
If you’re looking at this relationship as a blueprint, here is what actually makes it tick according to their own rare interviews:
- Privacy is a Choice: They proved you can be world-famous and still have a private life if you just... don't post everything.
- Shared Trauma as a Bond: They both survived child stardom. Finding someone who "gets the grind" without you having to explain it is a massive shortcut to intimacy.
- Humor over Romance: Every story they tell involves making fun of each other. From the failed first meeting to the garden gnomes, they prioritize laughing over "aesthetic" romance.
- Hands-on Parenting: Choosing not to have a nanny has forced them to be a team in a way most celebrity couples aren't.
The biggest takeaway from the Brenda Song relationship history is that the second act can be much better than the first. You might start out as London Tipton or Kevin McCallister, but you can end up as a normal, happy parent in a house full of gnomes.
Keep an eye on Brenda’s upcoming work on Netflix—she’s often said her family is the reason she’s finally comfortable taking on bigger, more challenging roles again. The stability at home clearly fueled the career comeback.