Brenda Song and Macaulay Culkin are one of the most random — and sweetest — couples in Hollywood. However, before the Suite Life of Zack and Cody star settled down with the Home Alone actor, she was in one other longterm relationship with a surprising . Keep reading for details inside Brenda’s former love life and exes.

When Did Brenda Song and Macaulay Culkin Get Engaged?

After five years of dating, reports that Brenda and Macaulay were engaged first hit in January 2022. The news came one year after the couple announced via Esquire magazine that they had welcomed a son named Dakota Song Culkin. The Disney Channel alum and former child star met in September 2017 when they filmed the movie Changeland together, which was released in 2019.

When Did Brenda Song and Trace Cyrus Date?

Brenda and Macaulay’s romance started shortly after Brenda called it quits with Miley Cyrus’ older brother, Trace Cyrus in 2017, after a tumultuous seven-year relationship.

While the Stuck In the Suburbs star and the Metro Station singer were together, they experienced a series of ups and downs starting from the moment they went public in May 2010. They got engaged shortly thereafter, with Trace announcing the news on X, formerly known as Twitter. “I am very excited to say, last week I asked my girlfriend Brenda Song to marry me and she said YES! We are both very excited to be engaged!” he wrote in October 2011.

However, months later the pair called it quits in June 2012.

Despite their split, Brenda and Trace continued an on-again, off-again relationship for several years. It wasn’t until February 2018, when the singer released a breakup song about the actress, that he confirmed their long-term love officially ended one year prior.

“This is not the video I intended to release today. But it seemed meant to be since I just got this video last night,” he captioned a since-deleted Instagram post. “I wrote this song last year in Nashville after Brenda [and] I broke up. Her and I have both moved on and I’m extremely happy for her. She inspired me to write countless songs and was such an important part of my life. I will always cherish songs I have like this one to remind me of our crazy [seven] years together.”

For his part, Trace dated Taylor Lauren Sanders shortly after his split with Brenda, and the two got engaged after less than one year of dating in 2018. However, things didn’t quite last. In January 2020, Trace confirmed their breakup and removed photos of his ex-fiancée from his social media.