All Of The Famous Men Brenda Song Dated Before Macaulay Culkin

Actor Brenda Song garnered public attention for her love life when she started dating "Home Alone" star Macaulay Culkin in 2017. According to People, their connection blossomed during the filming of the 2019 movie "Changeland," in which they both starred. During a 2018 episode of "The Joe Rogan Experience" podcast, Macaulay opened up to Joe Rogan about their relationship, humorously sharing, "I've got a special lady friend. We have a dog and a cat. It's one thing to exchange keys. It's another to get a cat." That same year, Brenda told Us Weekly, "I don't like to talk about my personal life, but everything's wonderful, and I'm happy."

The celebrity couple celebrated the arrival of their first child, a son named Dakota Song Culkin, in 2021, as reported by Esquire. Just over a year later, they welcomed another son, Carson Song Culkin, according to Us Weekly. In the meantime, they also got engaged, with E! News reporting on the news in January 2022.

Despite Brenda's openness about her relationship with Macaulay over the years, she had previously maintained a rather private stance on her romantic life, leaving much room for speculation regarding her past partners. While rumors linked Brenda to various famous men before Macaulay, most of the romances have remained unconfirmed.

In 2007, there were speculations surrounding Brenda Song's romantic involvement with two of her Disney Channel co-stars, Raviv Ullman and Aaron Musicant. Ullman and Song were both in "Phil of the Future," a sci-fi comedy series that ran from 2004 to 2006. On the show, Phil and Tia, their respective characters, were nothing more than good friends but had great energy together. This prompted fans to whisper about a potential fling off-screen, but despite their on-screen chemistry, there is no evidence to suggest a substantial real-life relationship between them. Notably, Song left the Disney show after eight episodes to take on the role of London Tipton in "The Suite Life of Zack & Cody."

That same year, Song met Aaron Musicant on the set of "The Suite Life of Zack & Cody." Fans were once again eager to see Song get with her colleague for real, given the on-screen connection between Musicant's character, Lance the Lifeguard, and Song's character, London. Although their characters dated on the show, any potential off-screen relationship between Song and Musicant was never officially confirmed, and the rumors were left unaddressed. Seventeen reported that Musicant later chose to leave the acting industry to pursue his passion for construction, designing, and building.

Rumors of a romantic connection between Brenda Song and yet another one of her "The Suite Life of Zack & Cody" co-stars, Jesse McCartney, surfaced throughout 2007 and 2008, following McCartney's guest appearance on the Disney Channel show as himself. In the series, Song's character, London, becomes infatuated with McCartney, who is a real-life singer, best known for hits like "Beautiful Soul" and "Leavin'." Speculation was fueled by their joint attendance at events, but it appears the duo never got into something more than friendship. Despite fans' hopes, there is no concrete evidence of a real-life romantic involvement between the two.

Additionally, Song was rumored to be dating Jason Dolley in 2008, another Disney Channel star. Dolley starred in "Cory in the House" from 2007 to 2008, coinciding with the last year "The Suite Life of Zack & Cody" was filmed, meaning the two could've easily bumped into each other on set. The Disney stars were spotted together at events, sparking relationship rumors. However, Song, known for maintaining her privacy, did not disclose any details about the alleged romance, and neither party addressed the rumors publicly.

Following the swirling gossip about her involvement with several Disney Channel stars, Brenda Song was romantically linked to rapper Flo Rida in 2009. Bossip reported sightings of the rumored couple at one of Flo Rida's Los Angeles performances, with eyewitnesses claiming that Song spent her time backstage during the concert and was later seen getting cozy with the rapper. They allegedly also left the venue together. While no further reports surfaced about their alleged relationship, Song did gush about Flo Rida's new song at the time, "Right Round," during an interview with Popstar Magazine that same year.

Shortly thereafter, TMZ spotted Song leaving a Los Angeles restaurant with singer Joe Jonas. The report detailed that the famous duo left Katsuya separately, with Song eventually getting into Jonas' car, which was parked at a distance. The pair were later spotted being comfortable with each other on multiple different occasions, but their fling was short-lived as Jonas went on to date Demi Lovato soon after, and Song got together with Trace Cyrus. The exact circumstances of Jonas and Song's initial meeting remain unclear, but according to MTV, Song made an uncredited cameo appearance in Jonas' movie "Camp Rock," suggesting that their paths may have crossed during its production.

Brenda Song's only public relationship before her involvement with Macaulay Culkin was with musician Trace Cyrus, who is Miley Cyrus' brother. Their romance became public in the spring of 2010, as reported by E! News, and the couple announced their engagement only a year later. Trace took to X, formerly known as Twitter, sharing, "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!" The tweet has since been deleted. Around the same time, rumors swirled that Brenda was pregnant with Trace, but her mother, Mai Song, debunked the speculations in an interview with Star magazine, as reported by RadarOnline.

In 2012, the couple decided to end their relationship, and Trace confirmed the split in a statement to People. "We split up a couple of months ago. We will continue to focus on our careers," he said, wishing Brenda all the best. However, despite the breakup, they reconciled and continued their on-and-off relationship for a total of seven years.

Despite their longevity, the famous couple did not have a happy ending. Brenda's relationship with Trace ultimately broke down for unknown reasons, officially coming to an end in 2017, according to PopSugar. A year later, Trace released a song titled "Brenda," inspired by their separation, where he appears to ask the actor for a second chance with the lyric, "I hope it's not really goodbye."