Macaulay Culkin and Brenda Song: The Guarded Romance

The lingering question remains: Are Macaulay Culkin and Brenda Song officially married?

Adding fuel to the speculation fire, the couple set tongues wagging when Brenda was spotted donning what appeared to be a wedding band alongside her exquisite teardrop engagement ring at Kat Dennings and Andrew W.K.’s November nuptials.

“On Jan. 26, People reported that Macaulay Culkin and Brenda Song are engaged. The endearing duo, parents to their first child, born in April 2021, have maintained a veil of secrecy around their relationship since they initiated dating back in 2017. 

Nevertheless, fans catch occasional glimpses of their love through snippets shared on social media or during rare joint appearances at public events.

Here, we unravel the discreet love story of these two.

June 2017: Culkin and Song meet

The two talented actors shared the screen in the film “Changeland,” a creation of Seth Green. Whispers of a budding romance surfaced when a photographer captured them sharing an intimate dinner at the renowned Craig’s restaurant in Los Angeles in July.

As the calendar flipped to September 2017, Song and Culkin ventured into the public eye with a double date, joining forces with their former director Seth Green, and his wife, Clare Grant. Observers noted the couple strolling hand in hand during a visit to Knott’s Berry Farm.

In 2020, Seth Green shed light on the unexpected revelation of Song and Culkin’s relationship in an interview with Esquire. Green confessed, “I didn’t see that one coming.” Culkin, in the same conversation, humorously reflected on the early days of his relationship, revealing a sentiment of awaiting impending doom.

“Something bad’s gonna happen. Someone’s gonna die!” Culkin quipped, encapsulating the unpredictability that kept him on his toes during the blossoming stages of their connection.

August 2018: Culkin’s playful baby plans

During an episode of The Joe Rogan Experience podcast in August 2018, Macaulay Culkin added a dash of humor to their love story. In a light-hearted exchange, he playfully discussed the prospect of starting a family with Brenda Song.

“This one’s a good one, so I’m probably going to put some babies in her in a little bit,” Culkin quipped with a grin. 

“I mean, we’ve definitely been practicing.” With a touch of anticipation, he envisioned the future, expressing, “I’m going to have some pretty babies. 

She’s Asian, so I’m gonna have tiny little Asian babies. It’s going to be adorable—a bunch of Sean Lennons running around the house, that’s what I’m looking for.” (Referring to John Lennon and Yoko Ono’s son, Sean Lennon).

September 2018: Song’s delight at a stand up to cancer event

In September 2018, Brenda Song shared glimpses of their thriving relationship during a Stand Up to Cancer event in Santa Monica, CA. Despite her usual discretion about personal matters, Song couldn’t help but express her joy. “It’s great!” she exclaimed to Us Weekly. 

“I don’t like to talk about my personal life, but everything’s wonderful, and I’m happy,” she added, letting a beam of happiness shine through.

April 2019: Bonding over shared stardom

As the pages turned to April 2019, Brenda Song unveiled a unique bond that tied her to Macaulay Culkin, Seth Green, and co-star Breckin Meyer. On the set of Changeland, the trio, all former child stars, found a silent understanding. 

Reflecting on her shared history with Culkin, Song revealed to Entertainment Tonight, “Child actors, we don’t even get to talk about it, you just look each other in the eye and you nod and we know.” 

Their shared experience as child stars served as an unspoken link, forging a deeper connection between them.

June 2019: Feline adventures at CatCon

In the summer of 2019, Brenda Song and Macaulay Culkin, accompanied by their celebrity friends, which included Song’s Dollface co-star Kat Dennings and Angela Kinsey from The Office, explored the world of famous felines. 

Amidst the charming chaos of CatCon, their shared love for these furry companions added another chapter to their enchanting journey.

December 2019: Welcoming “Santa Claws”

As the holiday season embraced them, Song and Culkin decided to add a furry friend to their family. Taking to Instagram, Song introduced their newest pet, “Santa Claws,” a Christmas gift from Culkin. 

This feline addition marked the beginning of a menagerie in their home. According to Esquire, their extended family now includes not only two more cats but also a parrot, several fish, and a Shiba Inu, creating a lively and diverse household.

August 2020: Birthday celebration on Instagram

Come August 2020, Brenda Song took to the virtual realm to celebrate Macaulay Culkin’s 40th birthday. In a heartwarming online tribute, she shared a snapshot of them sporting matching pajamas adorned with their names. 

Her caption said, “Happy 40th birthday to this magical being.” Song’s words painted a vivid portrait of Culkin’s virtues, expressing, “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.” 

Despite acknowledging that Culkin might not see her message due to his Instagram habits, she concluded, “My unicorn that I never thought could exist, I am the luckiest person in the world because I am loved by you.” This digital celebration encapsulated the enduring magic woven into their shared existence.

February 2020: Celebrating Mack’s essence

In the heart of February 2020, Brenda Song took the opportunity to express her admiration for Macaulay Culkin in an interview with Esquire. 

Gushing over his character, she shared, “People don’t realize how incredibly kind and loyal and sweet and smart he is.” 

She continued, “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.”

In the same narrative, Culkin playfully brought up the idea of “practicing” for children, stating, “We practice a lot. 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.’” 

April 2021: Welcoming Dakota Song Culkin

The spring of 2021 brought a momentous occasion for Macaulay Culkin and Brenda Song as they joyously welcomed their first child. On April 5, 2021, the couple publicly announced the birth of their son, named Dakota. 

Notably, the baby’s moniker, Dakota, carried a poignant significance, reportedly honoring Culkin’s sister, who tragically passed away in 2008. The couple’s decision to keep Song’s pregnancy under wraps added an element of surprise for their fans.

January 2022: A sparkling engagement

As the new year unfolded in January 2022, speculations about the couple’s engagement began to swirl. 

Both People and E! News, citing anonymous sources on Jan. 26, 2022, reported that Song and Culkin were officially engaged. The rumor mill kicked into high gear when Song was spotted wearing what appeared to be an engagement ring during a stroll through Beverly Hills. 

March 2023: New addition to the Culkin-Song clan

In a heartwarming revelation on Friday, March 17, 2023, Brenda Song and Macaulay Culkin shared the delightful news of expanding their family. 

The couple discreetly welcomed their second child, another son, just before Christmas in 2022. Although the newborn’s name remains a well-guarded secret, the announcement echoed the joyous occasion, marking a new chapter in their journey as parents.

November 2023: Spooky celebration together

As the Halloween festivities filled the air, Song posted an uncaptioned photo. 

The snapshot revealed Song adorned in a witch hat and costume, peering through the door at her better half, Macaulay Culkin, who sported what appeared to be a clown costume. 

This charming, candid moment showcased the couple’s shared enjoyment of life’s playful moments and added a touch of mystery to their holiday revelry.

December 2023: Culkin’s stardom shines on the Walk of Fame

The first day of December 2023 marked a momentous occasion for Macaulay Culkin as he received a star on the iconic Hollywood Walk of Fame. 

At the ceremony in Los Angeles, Culkin expressed heartfelt gratitude, acknowledging the pivotal role played by Brenda Song in his life. 

Visibly emotional, Culkin declared, “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 known, you’re the best person I’ve ever known.”

Song, wiping away a tear, listened as Culkin continued, “You’ve given me all my purpose. You’ve given me family. After the birth of our two boys, you’ve become one of my three favorite people.” 

The guarded love continues

While Macaulay Culkin and Brenda Song keep their love story private, the buzz around it never seems to fade. Their decision to stay low-key teaches us something valuable: love is personal, and it’s okay to keep it that way.

So, here’s to them and to all the love stories that don’t need a spotlight. May we all find joy in the simple, quiet parts of love that make it uniquely ours. In a world full of noise, there’s something beautiful about keeping love close and personal.