Angelo Massagli and Caitlin Hale met as co-workers. They were 10 years old. The pair, former child actors, were both cast in the 2003 film “School of Rock” in which Jack Black plays a substitute teacher who creates a rock band out of his classroom of musically gifted elementary-aged prep schoolers. Ms. Hale’s character was a braided pigtail-wearing backup singer named Marta. Mr. Massagli played Frankie, who was part of the band’s peewee security detail.
Mr. Massagli recalled being spontaneously asked to sing at his audition for the film in New York City. He was nervous to perform after Ms. Hale, who had just impressed the production team with her voice, including a rendition of “Everything’s Coming Up Roses” in which she changed the lyrics to be about the film’s director.
Back then, there was not even a hint of a youthful crush between them, the couple said. After the film’s release, the cast stayed in touch through a long-running group chat.
Ms. Hale, now 33, has a bachelor’s degree in journalism and public relations from Arizona State University. Mr. Massagli, 32, graduated from Northeastern University, majoring in English. After completing their undergraduate studies, both Mr. Massagli and Ms. Hale pursued further degrees, coincidentally both finding their way to schools in Florida, where they reconnected in 2018.
At the time, Mr. Massagli was a law student at the University of Miami. Ms. Hale was completing a bachelor’s of science and a master’s degree in health leadership at Nova Southeastern University in Fort Lauderdale. (Both eventually graduated from their respective programs. Mr. Massagli is now a lawyer for TikTok where he works as music product counsel. Ms. Hale is an Ob/Gyn sonographer.)
After realizing their proximity, the pair got lunch and caught up. They even sent a selfie to their moms.
Their relationship moved quickly, the years spent as childhood friends offering a strong foundation.
On an early date, Ms. Hale recalled going to the bathroom and returning to the restaurant table to find Mr. Massagli had ordered coconut cake for dessert, a flavor she’d previously mentioned was one of her favorites. She appreciated his close listening, she said.
Their wedding moved their journey to forever.
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