School of Rock Stars Appear Engaged 21 Years After Appearing in Iconic Movie Together

It was a match made in music class! School of Rock co-stars Caitlin Hale and Angelo Massagli have seemingly announced their engagement, 21 years after appearing in the iconic film together. The pair classmates Marta and Frankie in the 2003 movie starring Jack Black as their eccentric music teacher at a prep school. Sparks flew between the two in 2016 when they struck up a romance, and now, they're readying to walk down the aisle. Sharing an engagement-style photo shoot on Instagram, Hale, showed of a sparkling diamond ring as the pair pose for loved-up photos. While she didn't explicitly say they were engaged, she captioned the photos, "Sneak peek ????" -- and sparked rumors they would soon be saying, "I do" online. In the pics, Hale rocked a figure-hugging black gown, wearing her long blonde hair in a gorgeous updo, while Massagli sported a casual suit for the occasion. The couple first announced their romance in 2021 during an interview with Inside Edition, revealing they first began dating five years prior. Massagli said the pair reconnected when Caitlin moved to Florida, where he was living at the time. He found out about the move in "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." Speaking of his relationship with Hale, he told the publication, "The rest is history. This is locked down. Yes. This is it." Recalling the first time he met Hale during his audition for the movie, Massagli said, "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." While Hale has since retired from acting, completing a degree in journalism before settling on a medical career in New York, Massagli went on to achieve huge success playing the role of Bobby Jr. in The Sopranos until 2007. He ultimately stepped away from Hollywood as well, studying English with a minor in Business & Law at Northeastern University, before returning to New York to become an attorney.