Every Pitch-Perfect Detail of Brenda Song and Macaulay Culkin’s Love Story

And to be the best partners for each other, she and Culkin keep the conversation flowing.

“Brenda and I are very good at communicating with each other,” Culkin told E! News in December. “We have no secrets. We’re constantly on the line—we talk, we talk.”

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And presuming Song has slept at some point in the last couple of years, she wakes up knowing Culkin is there for her.

“As a new parent, I don’t sleep at all,” she told The Cut when Dakota was 9 months old, explaining how her routine revolved around her son. “I’m someone who likes to wake up and go-go-go. Now, it’s when I put my son down for his first nap that I get my work done. I take that time to do emails and plan my day. I try to do everything in his nap-time window. If I have time, I’ll work out—I have a little gym in my garage and do a lot of circuit training. To be the best mom, I have to be the best me.”

But at night, it was all about cozy time with Culkin.

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Changeland was an interesting big-screen opportunity—one she almost didn’t take—for Song, who broke out in Disney Channel‘s The Suite Life of Zack & Cody and had been working nonstop on TV (plus in films such as 2010’s The Social Network) ever since. 

But it was Culkin’s first major role in a decade, the Home Alone phenom having been content with quirky cameos, experimental film projects, painting and jamming with his band Pizza Underground for much of his adult life. He also wrote the 2005 book Junior, presented as a novel but admittedly inspired by his own life.

In the meantime, though, Culkin had supplied his voice to Green’s Adult Swim series Robot Chicken a few times, as had Song (never in the same episode), and it was their respective parts in the first-time filmmaker’s inner circle that brought them together.

Upon their return to Los Angeles, the first sighting on record of Song and Culkin occurred in July 2017 during the dinner rush at Craig’s in West Hollywood, a celeb-packed haunt where you don’t go if you’re trying to keep a relationship quiet.

They were spotted holding hands on what an eyewitness described as an “affectionate” double date to Knott’s Scary Farm that October with unwitting matchmaker Green and his wife Clare Grant. But Song and Culkin also spent a lot of time in Paris, where he had been living, and hopscotched to Amsterdam, Germany and various locales in the U.S. 

“Spending time traveling, you really get to know someone,” Song told Bustle. “Also, you really get to know yourself, because you start figuring out your strengths and weaknesses and how well you adapt. So we did that for about almost a year.”

And, simply, they’ve been together ever since, not ostentatious with their romance but happily chugging along, joining Green and Grant on a March 2018 day at Disneyland, appearing at Stand Up to Cancer and getting snapped by paparazzi on their coffee runs. (Though Culkin admitted to Esquire in 2020 that he was extremely worried in those early days that it was all too good to be true, that something would occur and blow it up.) 

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“I truly believe that he is the actor he is now because of all the things he had to go through,” Song told Esquire. “He has gone through so much tragedy; he’s had so many ups, so many downs; he’s seen the ugly side of this industry; he’s also seen the amazing side of this industry. So he can pinpoint exactly what he doesn’t want and what he doesn’t like about it. But yeah, I hope, I hope, I hope.”

She could have been talking about any number of things, but Culkin’s child stardom had been overshadowed in the mid-1990s by his parents’ bitter custody battle over their seven children, made all the more complicated because both Christopher “Kit” Culkin and soon-to-be ex-wife Patricia had been managing Macaulay’s lucrative career (as well as his younger brother Kieran‘s). And in December 2008, Culkin’s older sister Dakota was hit by a car and died the next day.

But the March 2020 Esquire cover shoot—which, Culkin noted, he did for fun, not to promote anything—also painted a picture of newfound domestic bliss for the admitted former “vagabond.”

“People don’t realize how incredibly kind and loyal and sweet and smart he is,” Song told the magazine. “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.”

The article shared that Culkin thoughtfully ordered banana pancakes along with his own 3 a.m., post-photo-shoot breakfast delivery so that they’d be there for Song when she woke up later that morning.

“I feed my lady,” he noted.

And never underestimate the power of laughter: Song shared that she kept a Moleskine notebook by her bed so she could jot down her boyfriend’s late-night one-liners.

After another interview session wrapped up, Culkin said he planned to go home, take a hot bath, watch a quick documentary, “kiss my animals, and go to sleep with my lady. I’m a man of really simple pleasures.”

But maybe not right to sleep?

Having ventured on the Aug. 6, 2018, episode of The Joe Rogan Show that he was “probably going to put some babies in her in a little bit,” and he and Song had “definitely been practicing,” he reiterated as much to Esquire 18 months later. “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.'”

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They didn’t have a nanny, Song said, but her mother had been living with them since Dakota was born.

“When I was working, my mom would bring him to set so I could breastfeed and see him during the day,” she continued. And she and Culkin were both “hands-on.”

“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,” Song 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.'”

Culkin has also taken their children’s anti-folk indie band cred into his own hands, captioning a photo of a Moldy Peaches album, “Giving the boys a musical education…” (The May 23 post was also his first public acknowledgment that there were boys, plural, at home.)

But becoming a mom had definitely altered Song’s approach to work—as in, it would now have to compete for time she’d rather be spending with her family.

“I never thought that I could really put my career in the backseat,” Song told E! News in February 2022, “but, at the end of the day, if I had to stop doing what I’m doing to be a better mom, I would do it without blinking an eye because my son is the most important thing and I just want to be the best mom for him.”

And she has credited Culkin, who knows from stepping back when the mood strikes, with helping her put her priorities first and not feeling so pressured to be constantly working.

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