How Macaulay Culkin Re-Proposed to Brenda Song With Help From Sons

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Brenda Song Shares How 'Home Alone' Inspired Safety Lesson for Her and Macaulay Culkin's Kids

Macaulay Culkin ram, erm, ran into a slight issue when popping the question.

The 45-year-old re-proposed to his longtime partner Brenda Song with some help from their two sons Dakota, 5, and Carson, 4, in August.

“I was coming home from Running Point and my mom texts me,” Brenda told Kylie Kelce on the April 30 episode of her Not Gonna Lie podcast. “She’s like, ‘Are you wearing makeup?’ And I was like ‘What?’ They had flowers all by the front door and my two boys.”

Although the Home Alone star had the proposal all planned out, things didn’t quite go as planned.

“I walk up and I’m like ‘Oh my God’ and he looked at my boys and he goes, ‘OK what do you say to mama?’” the Running Point actress explained. “And my youngest went, ‘Ram’s House!’”

A diehard Los Angeles Rams fan, Brenda has instilled a love for the football team in her children, confessing that they often practice cheers in their home.

“He’s so used to me doing callbacks because I’ll go, ‘Who’s house?’” the 38-year-old beamed. “And he’ll go, ‘Ram’s House!’ I’ve trained my kids well.”

As for Macaulay, he apparently told his fiancée, “We rehearsed and we rehearsed like, ‘Will you marry us?’” So, even though their little one may have gone off-script, Brenda was still delighted, noting, “My son instinctively knew ‘Ram’s House.’”

No stranger to football families herself, Kylie—who is mom to daughters Wyatt, 6, Elliotte, 5, Bennett, 3, and Finnley, 12 months, with ex-Philadelphia Eagles player Jason Kelce—quipped, “That’s outstanding. Raising ‘em right.”

Maya Dehlin Spach/FilmMagic

Before this re-do, the My Girl actor popped the question to the Suite Life of Zack and Cody alum in January 2022, following the birth of their first baby. After having their second kid soon after the proposal, their children have joined them for every milestone since, including Macaulay's Walk of Fame ceremony in 2023.

“That was such a special moment. We couldn’t have them miss that,” Brenda told Bustle at the time, noting that her sons weren’t fans of the photographers. “Dak was so scared of all the cameras. That’s one of the reasons why we sort of keep them away [from the spotlight]. They did not understand what was happening.”

Read on to see the sweetest moments between Mac and Brenda…

Macaulay Culkin/Instagram

So '90s

Macaulay Culkin and Brenda Song were on theme at Billie Lourd's 33rd birthday party in July 2025.

Brenda Song/Instagram

8 Years Strong

Brenda shared this sweet photo on the couple's eighth anniversary in June 2025, writing on Instagram, "There is still no one who makes me laugh or smile like the way you do. No one who makes me feel more seen, heard or loved."

"My partner in crime, my adventure partner, my best friend, my baby daddy, my favorite everything- thank you," she added. "To be loved by you is the greatest privilege."

Instagram/Brenda Song

Go Rams

Macaulay and Brenda were decked out in their favorite football team's colors in 2024.

Olivia Wong/Getty Images

Date Night

The couple stepped out for a rare red carpet date at a Clarins product launch party in Los Angeles in March 2024.

Instagram/Macaulay Culkin

Fun in Cabo

The couple celebrated Brenda's 36th birthday in Cabo San Lucas, Mexico, in 2024.

Instagram/Macaulay Culkin

Poolside Service

Macaulay purchased a resort tshirt and pretended to be a resort employee, offering Brenda a towel as she lounged poolside.

Instagram/Macaulay Culkin

Bellhop

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

Amy Sussman/Getty Images

Meet Dakota

The two appeared with their son Dakota at Macaulay's star ceremony on the Hollywood Walk of Fame in December 2023.

Amy Sussman/Getty Images

Hi Baby

Macaulay and Brenda's baby boy Carson also made an appearance at the ceremony.

Amy Sussman/Getty Images

Star Power

The couple were all smiles at the family event.

Instagram/Brenda Song

Trick or Treat

In 2023, the Home Alone star got into the spooky season spirit as Brenda passed out candy.

Michael Kovac/Getty Images for Ghetto Film School

Black & White Style

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

Kevin Mazur/Getty Images for Stand Up To Cancer

They're Getting Hitched

In January 2022, a source confirmed to E! News that Brenda and Macaulay were engaged. The actress showed off her engagement ring while stepping out in Beverly Hills.

Instagram

Heart Day

"Hoppy Valentine's day everyone!" Brenda shared on Instagram in 2020, when celebrating with Macaulay in the water.

Splash News

Take Me Away

While strolling through Friedrichshain in Berlin in 2018, the couple displayed some PDA by holding hands.

culkamania / Instagram

Proud Parents

In 2022, the couple celebrated their son Dakota's first birthday with a visit to Sesame Place San Diego. Calling it a "magical" affair, Brenda wrote on her Instagram alongside a snap of herself and Macaulay posing with Elmo, "We had so much fun!"

Instagram

Birthday Bash

"Happy 40th birthday to this magical being," Brenda wrote to Macaulay on Instagram in 2020. "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. But firstly, that would take me an eternity and secondly, you won't even see this because you don't ever use instagram. Hahaha. My unicorn that I never thought could exist, I am luckiest person in the world because I am loved by you."

Instagram

Biggest Cheerleader

"Guys, I did a podcast with my favorite bunny—podcasters and just 2 of my favorite people," Brenda shared online when supporting her boyfriend's podcast back in April 2018. "@bunnyearspodcast aaaand the one and only @mattbennett!"

Kevin Mazur/Getty Images