They first met as 10-year-olds on the sets of 'School of Rock.' Now, 22 years later they are married.

The year 2025 offers fresh perspectives and nostalgic moments that remind us how time flies. One such moment is the 22nd anniversary of the cult classic School of Rock, which first hit theaters in 2003. Fans of the film were delighted to learn that two of its child stars, Caitlin Hale (@caitlinmhale) and Angelo Massagli, recently got married. Their romance, which began years after meeting on the movie’s set, feels like a real-life fairytale, as reported by LADBible. Hale, now 33, played Marta, aka "Blondie," the confident backup singer in Jack Black's fictional rock band, while Massagli, also 33, portrayed Frankie, the "Tough Guy" and one of the band’s self-appointed security guards.

The pair met during the auditions for the movie in 2002 when they were just 10 years old. While Hale wowed everyone with a memorable performance of "Everything's Coming Up Roses" (with lyrics altered to honor the film's director, Richard Linklater), Massagli nervously sang Ozzy Osbourne's "Crazy Train." Filming began the following year, and all the young cast members quickly became close friends. Between takes, the kids attended lessons on set, bonded over shared meals at Benihana, and even joined their on-screen teacher, Jack Black, for games during downtime. Hale and Massagli insist there were no childhood crushes during filming, but their friendship laid the groundwork for their future relationship.

As time passed, the cast stayed connected through a long-running group chat, occasionally catching up and sharing life updates. Hale and Massagli eventually left acting behind. Hale pursued a career as a sonographer, while Massagli became a lawyer and worked as a music product counsel for at TikTok. Their lives converged again in 2018 when both were pursuing degrees at universities in Florida. They met for lunch to reminisce about their time on "School of Rock" and sent a selfie to their moms, who had also become friends during the production, as reported by the New York Post. That seemingly casual reunion marked the start of something more. After several more meet-ups and weekends spent together, the pair realized their connection had deepened.

Hale, while reflecting on their blossoming romance, recalled telling a friend, “I think I’m going to marry this guy.” Her instincts proved correct. In 2019, they moved to Brooklyn together, and by June 2023, Massagli proposed in front of the Temple of Dendur at the Metropolitan Museum of Art. They celebrated the engagement with an elegant dinner and Champagne at iconic New York venues. Though they legally married last year, Hale and Massagli celebrated their wedding on January 4, 2025, with a grand celebration at the Park Château Estate & Gardens in New Jersey. The luxurious venue was the perfect backdrop for their big day, which included a cocktail hour, a three-tiered wedding cake, and cannoli served on the dance floor. 

The couple's wedding turned into a mini "School of Rock" reunion, with nine cast members in attendance, including Rivkah Reyes, Aleisha Allen, Z Infante, and Joey Gaydos Jr., according to Entertainment Tonight. Jack Black couldn't attend but sent a heartfelt video message, which Hale described as "generous and sweet." During the reception, the cast joined Hale and Massagli for a nostalgic dance to Stevie Nicks' "Edge of Seventeen," a nod to the film's iconic scene between Black and Joan Cusack's characters. Hale called it a "time capsule moment", as they instinctively moved in sync, recapturing the magic of their on-screen chemistry.