Surprise! Brenda Song and Home Alone star Macaulay Culkin are officially parents, taking their longtime love to the next level.

In April 2021, the couple announced via Esquire magazine that they had welcomed a son named Dakota Song Culkin nearly four years after they first sparked romance rumors in September 2017. The Disney Channel alum and former child star met when they filmed the movie Changeland together, which was released in 2019. Their romance started shortly after Brenda called it quits with Miley Cyrus’ older brother, Trace Cyrus, for good after a tumultuous seven-year relationship.

While the Suite Life of Zack and Cody 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 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.

Months later, in June 2012, the pair called it quits. “Brenda and I have decided to go our separate ways,” the musician shared in a statement at the time. “We split up a couple of months ago. We will continue to focus on our careers. I wish Brenda the best and much success in the future. I hope everyone can respect our privacy about this situation. Thanks so much.”

Despite their breakup, Brenda and Trace continued their on-again, off-again relationship for years. It wasn’t until February 2018, when the rocker 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.”

Brenda went on to date Macaulay while Trace, for his part, moved on with Taylor Lauren Sanders.

Get ready for a major walk down memory lane! Scroll through our gallery for a complete timeline of Brenda and Trace’s past seven-year relationship. 

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