8 Adorable Brenda Song & Macaulay Culkin Moments That Tugged At Our Heartstrings

For nearly a decade, Brenda Song and Macaulay Culkin have built one of Hollywood's most beloved love stories. The two first met in 2014 at Seth Green's house, but it wasn't until 2017 that they reunited in Thailand on the set of "Changeland" that they grew a liking for each other and began dating the same year. In 2021, they welcomed their first son, Dakota, and got engaged shortly after. Even though the pair haven't tied the knot yet (maybe they'll join these celebs who got married later in life), they often share glimpses of their relationship, leaving fans swooning. 

Whether they're celebrating major career achievements, embarking on fun-filled adventures together, or simply gushing about one another in interviews, Song and Culkin consistently remind us why they're such a beloved couple — and show tons of signs that they're in a healthy relationship. They feel refreshingly grounded, proving that some of the strongest Hollywood romances don't need constant headlines to capture hearts.

In 2026, the couple celebrated their nine-year anniversary with sweet tributes on Instagram. Culkin shared an adorable date night photo, stating, "It's been 9 years since my life changed forever. It's amazing to think that 1 in every 5 days I've been alive, I have had the honor of waking up next to the love of my life." 

Song posted a Polaroid of the two, writing, "My life burst into color when you walked into it. I will never know what I did to deserve you and this life that we lead, but I am forever grateful."

Macaulay Culkin received a star on the Hollywood Walk of Fame in 2023, where his big day also served as a rare public appearance with Brenda Song and their two sons, Dakota and Carson. During the induction ceremony, Song was photographed wiping away tears as the "Home Alone" actor praised his fiancée throughout his speech. 

"I'd like to thank Brenda. You are absolutely everything. You're my champion ... You're not only the best woman I've ever known, you're the best person I've ever known. You've given me just all my purpose. You've given me family," he stated (via Harper's Bazaar).

Brenda Song and Macaulay Culkin proved that while they are serious actors, they're also kids at heart. The couple took a trip to Legoland California, where they quickly realized they looked more like California tourists than residents. 

Dressed in Crocs, tube socks, and sunhats on their guided tour, they went all in, taking pictures at all the important landmarks, stopping for a quick nap on benches, and getting lost — the full tourist experience. Song and Culkin prove that poking fun at yourself every once in a while is sorely needed.

In 2025, the internet was in a frenzy, debating which teen idols belonged on the "Disney Channel Mount Rushmore." Former stars of the network and other celebrities echoed names like Miley Cyrus, Selena Gomez, Hilary Duff, and many others. However, Macaulay Culkin had only one person in mind: Brenda Song. 

He posted a photo of Brenda Song in all of her Y2K glory on Instagram with the caption, "Not that anyone asked, but I'm throwing my hat into the debate. THIS is my Disney Channel Mount Rushmore." From one hotel kid to another, the gesture was undeniably adorable.

Macaulay Culkin and Brenda Song proved they're as well-synchronized with their fashion as they are with their love. The two sat in the stands of the 2026 Super Bowl wearing matching Oakley Meta Sunglasses. 

The blue-tinted shades were just the cherry on top of their thoughtfully coordinated looks, as they both sported Rams letterman jackets, Song's in black and Culkin's in royal blue. While they weren't full-on twinning, the adjacent looks emphasized their chemistry, proving that even on football's biggest night, the couple knows how to make a fashionable statement together.

For Brenda Song's birthday, Macaulay Culkin treated her to a life of luxury — the suite life, if you will. The couple took a trip to the Nobu Hotel, where Culkin spotted a shirt in the gift shop that resembled the staff uniforms. 

He took it upon himself to spend the vacation playing every role imaginable: poolside waiter, housekeeper, cabana boy, room service attendant, and bellhop. He waited on the birthday girl hand and foot, fully committing to the bit and turning a relaxing getaway into an adorable display of devotion.

Nothing says "I love you" more than willingly giving up a night on the couch to hang out with each other on the red carpet. Brenda Song and Macaulay Culkin attended the fifth annual Academy Museum Gala, where Song wore a gorgeous Carolina Herrera gown, and Culkin wore a Paul Smith suit jacket. 

Later, she took to Instagram writing, "You know when you have a night off from the kids and you just wanna curl up with your significant other in front of a fireplace ... Mama and papa got gussied up and were lookin' FRESH and FANCY y'all!!!."

Macaulay Culkin and Brenda Song prove that any night can be date night when you're madly in love. While in New York City for "Running Point" press, Song appeared on "The Tonight Show," while Culkin hung out backstage. 

In an Instagram dump, the actor posted a mirror selfie in the dressing room in a blue gown while her partner is standing behind her in a cozy sweater and jeans. The couple proves time and time again that, amongst the red carpets and flashing bulbs, there is beauty in the quiet and still moments, making them a fan-favorite celebrity couple.