These “School of Rock” Costars, Who Met as Kids, Are Sparking Engagement Rumors

When School of Rock first aired in 2003, the comedy film was a smashing success, earning praise from movie critics and viewers alike. The motion picture about a guitarist posing as a substitute teacher and turning his students into a band was filled with humorous lines and stellar performances. One particular quality that led to its initial triumph and long-lasting legacy was the onscreen relationships. And for one pair of costars, Caitlin Hale, who played Marta, known as “Blondie,” the band’s backup singer, and Angelo Massagli—the band’s security guard, a romance between the two of them began offscreen over a decade after the film was released. Now, there’s speculation that a wedding may be in the works for the longterm couple.

The pair sent fans into a frenzy when Hale posted a carousel of black-and-white couple portraits shot in Brooklyn—which is reminiscent of an engagement shoot—on her Instagram on September 27, 2024. Eagle-eye fans noticed that Hale sported a diamond ring on her left ring finger in the last photo in the collection, which sparked excitement that the pair, who have been dating since 2016, might be engaged.

Another clue? Hale even tagged Royal Brides By Send K. Ceka, a bridal hair and makeup artist, who seems to have done her glam for the photoshoot. While the actress didn’t tag the photographer of the images, wedding photographer Julian Ribinik Studios seemed to have claimed responsibility for the photos. “Look at these two beautiful people!!” husband-and-wife team Julian and Evgenia Ribini wrote. “Thank you so much for the honor! 🔥🔥🔥.” Better yet, Hale even appeared to have teased a future announcement with her caption. “Sneak peek 😘,” she wrote.

After School of Rock hit theaters in 2003, the cast stayed connected in their adulthood over text. “We have a group chat where all the School of Rock kids, we just hit each other up whenever someone moves somewhere new or is doing something different,” Massagli told Inside Edition. A decade after the film was released, the actor reached out to Hale once he realized she was moving to Florida, where he was living at the time. After she got settled in, they met up for lunch, dinner, and drinks—and Hale was smitten. “The rest is history,” Hale said. “This is locked down. Yes, this is it.”

Even though they didn’t start dating until 2016, Massagli told the outlet that he was taken with Hale from the first time they met while auditioning for School of Rock. “I remember my first audition for School of Rock like it was yesterday,” he told the outlet. “I get in there, and the little blonde girl next to me, she gets called in first, and she starts singing show tunes and just blows the roof off the place. It was excellent.”