Go Inside Macaulay Culkin and Brenda Song's Private Road to Engagement

After becoming parents in April, Macaulay Culkin and Brenda Song have taken another big step in their relationship by getting engaged. Look back on how the private stars fell in love.

By Mike Vulpo Jan 26, 2022 7:30 PMTags
Watch: Macaulay Culkin & Brenda Song Welcome Baby No. 1

Macaulay Culkin and Brenda Song have quietly built a very special home.

In case you missed the big news, a source confirmed to E! News that the longtime couple is engaged. While details surrounding the proposal remain private for now, Brenda was spotted wearing a ring on that finger while stepping out in Beverly Hills on Jan. 25. 

The news comes more than nine months after the couple welcomed their first child together. And yes, they managed to keep their pregnancy journey a secret until baby Dakota Song Culkin officially arrived.

It's exciting news for a pair who grew up in the spotlight together and yet still managed to keep their relationship on the private side. While they first sparked romance rumors back in 2017, both Brenda, 33, and Macaulay, 41, have tried to keep their relationship off Instagram and red carpets. At the same time, the duo has dropped hints that they are more than happy together.

"This one's a good one, so I'm probably going to put some babies in her in a little bit," Macaulay shared on a 2018 episode of The Joe Rogan Experience podcast. "I mean, we've definitely been practicing."

2021 Celebrity Babies

Now, scroll on to see their cutest moments, from PDA-filled getaways to heartfelt birthday posts. There's a lot of love to go around.

Parents of Two

The two step out in Los Angeles in April 2023, months after welcoming their second son.

They're Getting Hitched

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

Heart Day

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

Take Me Away

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

Birthday Bash

"Happy 40th birthday to this magical being," Brenda wrote to Macaulay on Instagram. "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."


Uniting for good! The Hollywood couple attended the sixth biennial Stand Up To Cancer (SU2C) telecast in Los Angeles. 

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!" 

Proud Parents

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!"

This story was first published on Monday, April 12, 2021 at 11:52 a.m. PT.