Brenda Song and Macaulay Culkin’s Romance: From Fling to Family

Brenda Song and Macaulay Culkin’s romance is straight out of a rom-com.  

Back in the year of 2022, when the world was still spinning, I, a die-hard fan, found myself utterly captivated by the news that a Disney Channel alum and none other than Macaulay Culkin, the iconic Kevin McCallister from “Home Alone,” had gotten engaged. But here’s the twist – their love story isn’t your typical boy-meets-girl tale. Instead, it seems to follow the path of foes-turned-lovers, a trope that has always intrigued me in stories and movies alike.

On an episode of “The Drew Barrymore Show” that aired on March 10th, Brenda mentioned to host Drew Barrymore that they had first crossed paths through a mutual acquaintance. However, she admitted that she can’t recall their initial encounter.

Although their initial encounter didn’t quite ignite the fire of their love, the 36-year-old looked back fondly at the early stages of learning about the other child star they met.

She clarified, “The first encounter I recall having with him was when the show we were both on with a mutual friend got terminated. He tried to lighten the mood by saying something humorous: ‘You know, the show wasn’t all that fantastic anyways, you two are doing just fine.’

She confessed that she didn’t care for him in the least, “and as if on cue, he gradually moved towards the door.” In a casual manner, he said, “I think I’ll go now.

A couple of years passed before their shared acquaintance reunited them for a film project they co-wrote, directed, and acted in.

The person acting as the matchmaker requested his acquaintances to join him in Thailand for filming purposes, and during our stay, Mac and I worked approximately 10 days altogether, yet we remained there for six weeks before getting acquainted. As time passed, it seemed he might become my best friend, but then I realized, “Oh, it appears I have feelings for him.” The actor from ‘Suite Life’ shared this reminiscence later on.

However, despite these fresh emotions arising, Brenda hadn’t anticipated that her fleeting affection would develop into an enduring romantic involvement.

The actress from “Running Point” playfully commented, “I believed it was going to be my initial romantic adventure.” Surprisingly, this brief encounter has blossomed into nearly eight years together and the arrival of two children.

Ever since what started as a casual connection morphed into one of my all-time favorite duos in Tinseltown, I’ve been utterly smitten! You know who I’m talking about—the charismatic actor whose roles have always left me in awe, especially his portrayal of “Richie Rich.” This man, who shares two adorable sons, Dakota (3) and Carson (2), with the stunning actress, has become an integral part of my heart.

When this dashing gentleman received a star on the Hollywood Walk of Fame in December 2023, I couldn’t help but feel a surge of pride, knowing how deeply he cherishes his partner. His heartwarming speech during that special moment was a testament to their unbreakable bond and left me with a warm fuzzy feeling all over!

You are everything to me! You’re my biggest cheerleader. You’re the only one who’s happier for me today than I am myself. Beyond being the best woman I’ve ever met, you’re simply the finest person I’ve ever encountered.

“You’ve given me all my purpose,” he continued as he started to choke up. “You’ve given me family.”

For more of a glimpse into Brenda and Macaulay’s adorable romance, keep reading.

Macaulay Culkin and Brenda Song were decked out in their favorite football team’s colors.

In March 2024, the pair ventured out for an uncommon evening together on the red carpet, attending a Clarins product debut party held in Los Angeles.

In December 2023, the pair were present alongside their child named Dakota at Macaulay’s star unveiling event on the Hollywood Walk of Fame.

At the event, Macaulay and Brenda’s newborn son (who hasn’t had his name revealed yet) was present as well.

The Home Alone star got into the spooky season spirit as Brenda passed out candy.

The duo appeared at the GFS Fall Benefit in Santa Monica, Calif., in October 2023.

In April 2023, Brenda and Macaulay were spotted holding hands while they were out together, approximately a few weeks following the confirmation of the birth of their second child.

It was reported by TopMob News in January 2022 that Brenda Song and Macaulay Culkin became engaged. The actress was spotted flaunting her engagement ring during an outing in Beverly Hills.

On Instagram, Brenda cheerfully wished everyone a “Joyful Valentine’s Day!” as she celebrated it alongside Macaulay in the water.

In December 2023, the couple beamed with joy during Macaulay’s star unveiling on the Hollywood Walk of Fame.

As they leisurely walked around Friedrichshain in Berlin, Germany, the pair showed affection by intertwining fingers.

Brenda posted on Instagram: “Happy 40th birthday to this extraordinary individual, Macaulay! I could go on and on about your outstanding qualities – kindness, love, genuineness, loyalty, honesty, intelligence, and humor. But let me start by saying that a) it would take forever and b) you probably won’t even see this since you never use Instagram. Laughs! The mythical creature I never thought was real, I consider myself the luckiest person in the world for having you as part of my life.

Joining forces for a noble cause! The popular Hollywood duo graced the sixth bi-annual Stand Up To Cancer (SU2C) live broadcast in Los Angeles.

In April 2018, Brenda posted online about a podcast she did with her two beloved friends, who also happen to be podcasters, specifically the bunny-themed one (@bunnyearspodcast) and Matt Bennett. “@bunnyearspodcast and none other than @mattbennett!

Instead of heading out for a casual day, the family marked Dakota’s first birthday by making a trip to Sesame Place San Diego. Brenda described it as a “wonderful” occasion on her Instagram post, complete with a photo of herself and Macaulay grinning alongside Elmo, saying, “We had such a fantastic time!

The couple celebrated Brenda’s 36th birthday in Cabo San Lucas, Mexico. 

Macaulay bought a resort t-shirt and acted like a resort worker, giving Brenda a towel while she was relaxing by the pool.

He also played bellhop and carried her bags, much to Brenda’s confusion and amusement.

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2025-03-13 16:48