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.
“I was like, ‘wow, that girl’s really, really, really something else,’” Mr. Massagli said. He performed the only song he knew the words to at the time: “Crazy Train” by Ozzy Osbourne.
A year later, the pair and the other children cast in the film spent several months shooting the movie in New York. The group bonded quickly, Ms. Hale said, attending real school on set and having meals at Benihana. Mr. Black, the film’s adult star, would eat lunch with the group and play games between scenes. Their moms, often present on set, also became close during this time.
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.
Eventually, Mr. Massagli and Ms. Hale both left show business to pursue other careers.
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.
“We thought that was kind of it,” Mr. Massagli said. “But we just kept grabbing dinners and going out for the weekends. We were like, ‘something’s brewing here.’”
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 relationship moved quickly, the years spent as childhood friends offering a strong foundation.
“Even though it wasn’t romantic, that familiarity we had and our families had when we were younger, really cut through some of those early relationship hurdles,” Mr. Massagli said.
“I knew very early,” Ms. Hale said. “I actually said to one of my close friends, I remember being in an Uber on the way down to Miami one weekend and we were going out and I was like, ‘I think I’m gonna marry this guy.’”
The first time Mr. Massagli told Ms. Hale he loved her his exact words were, “I think I love you.”
“You think?!” Ms. Hale exclaimed in pseudo-exasperation.
Later that year, Mr. Massagli offered up his home as a short-term stay to help Ms. Hale cut down on the commutes between her home in Fort Lauderdale and a residency program in Miami. He was going out of town for a week and gave her a key and permission “to crash.” By the time he returned, she had moved in.
The couple moved to Brooklyn in 2019 and got engaged in June 2023 at the Metropolitan Museum of Art. Mr. Massagli proposed in front of the Temple of Dendur, the light-filled gallery featured in the film “When Harry Met Sally…” Dinner at Nino’s, an Upper East Side Italian restaurant, and champagne at the Carlyle followed. Upon hearing the news via FaceTime, Mr. Massagli’s mother burst into tears.
For their wedding, the couple knew they wanted to “go all out,” Ms. Hale said. On Jan. 4, they celebrated their wedding at Park Château Estate & Gardens, a Versailles-like wedding venue in East Brunswick, N.J. (They had previously made things legal on Aug. 30 at Brooklyn Borough Hall. Waldo Ramirez, a staff member of the City Clerk’s Office, officiated.)
Ms. Hale started her day at 8:30 a.m. getting glammed up for the evening celebration. Ms. Massagli had a more leisurely morning, including a massage.
The couple, who now live in Long Branch, N.J., had read private vows to each other the night before the main event. Ms. Hale’s father, Gary Hale, officiated a brief ceremony before the party began.
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Guests were then whisked into cocktail hour where they sipped the couple’s signature drinks: a Bellini for her and a dirty martini with blue cheese olives for him. The venue was decorated with exclusively white flowers and, per Ms. Hale’s vision, many, many white candles.
For the reception, Ms. Hale changed into a pair of custom-made rhinestone-studded, thigh-high Berta boots that peeked out of the slit of her strapless gown.
“Once I saw those boots, I was like, I need to do whatever I can to make sure to have those,” she said. “The dress can follow.”
The couple entered the reception to “Through the Wire” by Kanye West, which transitioned into Chaka Khan’s “Through the Fire” for their first dance. They asked their D.J. to play songs that felt like “if Studio 54 never closed,” Mr. Massagli said. A live saxophone player roamed the party riffing over the piped-in music.
During “Edge of Seventeen” by Stevie Nicks, the duo danced with their castmates from “School of Rock,” a nod to a bar scene from the film. Nine cast members were there, as well as more than a dozen of the actors’ parents and siblings. (Jack Black politely declined, citing an ongoing film project, but “was so nice and generous with his words and definitely commemorated it privately,” Ms. Hale said.)
Not wanting to throw off the party vibe, at one point Ms. Hale and Mr. Massagli stepped away for a private cake cutting where they fed each other “delicate, small bites,” Ms. Hale said, laughing.
Ms. Hale recalled another moment on the dance floor with her fellow former “School of Rock” backup singers as a “time capsule moment.”
“We were just dancing together to some old-school disco and then there was some sort of ad lib in the song and we all just hit it,” she said. “We looked at each other and we’re like, ‘That just happened. We still got it.’”
On This Day
When Jan. 4, 2025
Where Park Château Estates and Gardens, East Brunswick, N.J.
The Family Stone Both the bride and groom wore sentimental rings. Mr. Massagli’s wedding band was passed down from his grandfather. “He’s big Ang, I’m little Ang,” Mr. Massagli said. Ms. Hale’s oval diamond engagement ring was a repurposed ring from her mother.
Late Night Snacks In addition to a three-tiered wedding cake — each tier was a different flavor — guests were served cannoli on the dance floor. When the night ended, guests walked out past a food truck handing out McDonald’s.
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