Brenda Song And Trace Cyrus' Relationship Didn't Last (& He Wrote A Song About It)

Miley Cyrus' older half-brother, Trace Cyrus, became a household name back in 2007 when his band, Metro Station, released the super catchy single "Shake It." Despite showing such early promise, they ended up being a one-hit wonder, and these days, we don't really hear from Trace Cyrus anymore. In 2017, he tried his best to launch a solo musical career, but that didn't really go anywhere either. Now, the only way he seems to make headlines is with his love life.

Like his famous sister, Trace hasn't always had the best luck regarding his personal life, and his dating history has been marked by highs and lows, as well as some recognizable names. From 2005 to 2008, the tattooed frontman was linked to influencer Hanna Beth Merjos before getting together with Demi Lovato in 2009. That union was short-lived, though, with Trace telling People that conflicting work schedules and an age difference (he was 20 while she was 16) were their downfall. "Maybe when she's older and we've both matured, we'll be looking for the same thing and it can work out," he mused. Jump to 2018, and he got engaged to Taylor Lauren Sanders before calling off the nuptials in 2020.

However, Trace's most headline-making romance was undoubtedly with Brenda Song. The couple had a drama-filled union that lasted years — and we're revisiting it below.

Before Brenda Song met and fell in love with Macaulay Culkin, the actor had a lengthy on-again, off-again relationship with Trace Cyrus. Yes, Miley Cyrus' older brother. The "Suite Life of Zack and Cody" star first started dating the musician back in 2010, and the pair actually got engaged in October 2011. Trace broke the happy news in a since-deleted tweet saved by Entertainment Tonight, in which he enthused, "I am very excited to say, last week I asked my girlfriend Brenda Song to marry me and she said YES!" Miley was all for it, responding, "Can't wait for Brenda to be a Cyrus." Unfortunately, that never happened. In June 2012, the couple ended their engagement with Trace telling People they had called it quits months earlier and sharing, "We will continue to focus on our careers."

Even so, it wasn't totally over. In 2013, E! News spotted the exes spending time together in California just as Song cryptically tweeted, "Don't give up on someone you can't go a full day without thinking about." Jump to May 2015, and they split again as Trace publicly accused Song of pretending to be pregnant. In an Instagram post saved by J-14, the actor wrote, "I apologize for not clearing this up sooner and for the continual damage that these lies have caused @TraceCyrus." Trace clapped back, "Yes they were lies THAT U MADE UP and told me, my entire family and all our friends." By June, though, they appeared to have reconciled again.

Brenda Song and Trace Cyrus' relationship had its share of ups and downs, but after what Cyrus called a "crazy 7 years together," it ended for good in 2017. The singer confirmed the news of their permanent split on Valentine's Day 2018 when he celebrated the romantic holiday by releasing a breakup song aptly called "Brenda." In a since-deleted Instagram post seen by Teen Vogue, Cyrus explained he had penned the track after their final breakup and found it to be a cathartic process. At the same time, he vowed never to write about his ex again. "Her and I have both moved on and I'm extremely happy for her," he told fans. "She inspired me to write countless songs and was such an important part of my life."

Reading through the song's lyrics, it appears that Cyrus decided to take much of the blame for the failure of their union. "Did I let you down / When I wasn't round?" he asks. "Brenda, I should've never left the west coast." Overall, it reads like an apology letter while revealing Cyrus' sadness. The song isn't without its cheeky moments, though, as he sings, "Brenda, yeah you drive me crazy / But I miss my baby tonight."

Cyrus may have lost his love, but he gained loads of fans who appreciated the message and catchiness of the tune. One even gushed, "This sounds like something early Taylor Swift could've written."