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

It appears that the couple that wakes together and draws lightsabers to decide who calms the crying baby stays together.

That was the superfan tableau that Brenda Song and Macaulay Culkin signed up for last November to tout Star Wars apparel for holiday gift-giving, the mom and dad of now two sons—2-year-old Dakota Song Culkin and another baby the pair quietly welcomed this year without public fanfare—adding an intergalactic twist to one of the most relatable parenting scenarios.

"As a new parent, I don't sleep at all," Song 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 her fiancé.

"My boyfriend and I always get into bed and chat about our days and the next day," Song—still days away from getting engaged when she gave the interview—said. "When I was working he'd wake up with me to chat. Now we do it at night, after our son goes down. It calms me. It sounds small, but I cherish it. It's nice to wind down with someone you love."

It's only fair they help each other relax, considering the jumpstart they gave each other's hearts when they spent seven weeks shooting the drama Changeland on location in Thailand. 

"I didn't see that one coming," director Seth Green, who's been buddies with Culkin since they co-starred in 2003's Party Monster, told Esquire of the romance his film provided the idyllic surroundings for in the summer of 2017.

But, as the couple revealed on the April 18, 2018, episode of Culkin's Bunny Ears podcast, the 42-year-old and Song, 34, first met in 2013 when he visited the set of Dads, a short-lived sitcom starring Green and Giovanni Ribisi as video game execs whose...wait for it...dads move in with them. Song played their crafty assistant.

"Yeah, she totally brushed me off, completely," Culkin recalled. "I was focused," she countered.

Song denied that she didn't like him at the time and brushed off his joke that she was put off by his "reputation." Prodded by guest Matt Bennett to share what turned her off, though, she deadpanned, "It was the man bun."

In any case, Culkin—who divorced Rachel Miner in 2000 after two years and was in a relationship with Mila Kunis for the better part of the '00s—would be dating Jordan Lane Price by the end of 2013, and that went on until 2017. Song ended an engagement to Trace Cyrus in 2012, but they remained friends and were reportedly off-and-on until... also 2017. 

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.

"Right up until we were about to film, I actually had a couple roadblocks," Song recalled to Bustle last year. "I was like, 'Am I not meant to go?' Another project came along and I was like, 'No, I want to spend seven weeks in Thailand with some of my best friends.' My manager was like, 'Are you sure? You're turning down this job to go do a little indie...' It was the best decision I ever made because I met my boyfriend and then we spent a lot of time traveling. I'd never really done that."

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.) 

In addition to having mutual friends, Song and Culkin had both been acting since they were little kids, a shared connection that they didn't even have to talk about. "You just look each other in the eye, and you nod and we know," she quipped to Entertainment Tonight ahead of Changeland's June 2019 release.

Later that year, Culkin guest-starred on Song's Hulu series Dollface, playing a love interest for Shay Mitchell's character who Song suspects just might be a serial killer. He's since been on American Horror Story and The Righteous Gemstones, and lent his voice to the 2022 animated film Entergalactic.

"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.'"

Well, you know what they say about practice.

When their son was born on April 5, 2021, they named him after Culkin's late sister and said in a brief statement that they were "overjoyed."

Twelve weeks later, Song started filming the second season of Dollhouse—which, she later acknowledged, was a lot to take on so soon after giving birth.

"People tell you a lot about labor and pregnancy, but not about the fourth trimester," Song told The Cut in an article published Jan. 31, 2022, six days after her new, massive engagement ring made headlines. "To my girlfriends that are pregnant I say, make sure you have help. Because your instinct is to want to do it all and you physically can't."

On a typical work day, "I'd be up around 4 or 4:30 a.m., go over my notes and scenes, and sneak in to give my son a kiss. On set you spend an hour in hair and makeup, and then there's not a whole lot of downtime from there. I'm not working in a coal mine or a hard labor job. What's difficult is the mental drain. You're not just working from 'action' to 'cut,' but from the moment you step onto set until you're in your car headed home. Your energy drives the pace of the show, but keeping it going all day is exhausting."

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 last February, "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.

"That's something that I admire and respect so much because, in every case—personal life, professional, or anything—he always stays true to himself because he's been judged in every way, shape, or form," Song told Bustle. "Watching that was shocking because it's also very different for me."

As an Asian American woman, she continued, "There's always that fear that the opportunity will not be there again. That's something that I've had to get over. That fear of going, 'I don't have a lot of opportunities. So if I say no, they might not come back.'"

"I realized I had to be okay with letting those things go," she concluded, "because, at the end of the day, staying true to myself was more important. Watching someone who makes decisions that are solely based on their happiness and well-being is very inspiring and it's taught me a lot because it's hard. It's hard to not say yes to things when everyone's like, 'You should to it.' I think where I am in my life has a lot to do with my partner and being a mom."

(Originally published Feb. 14, 2023, at 6 a.m. PT)

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