Rock got no reason, rock got no rhyme … but it can lead to a love story. School of Rock costars Caitlin Hale and Angelo Massagli are seemingly engaged 21 years after they filmed the Jack Black-led comedy movie.
Caitlin, 33, teased the possible relationship news in an Instagram post on September 26. The former child actress shared a carousel of black and white professional photos showing her and Angelo, 32, dressed in formalwear as they posed on a balcony and in front of a brick wall in Brooklyn, New York. Though the photos were mostly taken from far away, Caitlin appeared to be wearing a diamond ring on *that* finger.
“Sneak peek,” she wrote in the caption with a blowing-a-kiss emoji.
Though the couple did not confirm their engagement in the post, many fans guessed that they had taken the next step in their relationship after eight years of dating.
“So rock n roll IS about scoring chicks!” one fan commented, referencing one of Angelo’s character’s lines in School of Rock.
“Congratulations to the actors who played my two favorite characters in School of Rock!” another user wrote.
Their School of Rock costar Rivkah Reyes, who played Katie in the movie, simply commented, “BABESSS.” Jack, 55, who played their rock teacher, Dewey Finn, liked the post.
Caitlin played Marta, a.k.a. “Blondie,” one of the backup singers in Dewey’s band of students at Horace Green Prep School. Meanwhile, Angelo played “Tough Guy” Frankie, a member of the band’s security team.
Caitlin and Angelo began dating in 2016 after they reconnected via a cast group chat, he revealed to Inside Edition in 2021. “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,” he explained. “So Caitlin is like, hey, I’m moving down to Florida.”
The pair met up for lunch and continued to see each other after that.
“The rest is history,” he added. “This is locked down. Yes. This is it.”
Following the film’s release in 2003, Angelo — who had already appeared in seven episodes of Cosby in the late ‘90s, as well as a 2001 episode of Counter Kid and the 2002 movie Stuart Little 2 — briefly continued his acting career. He had an 18-episode stint on The Sopranos as Bobby Baccalieri Jr. from 2002 to 2007 and appeared in one episode of Cupid in 2009.
However, Angelo left acting to pursue a law degree from the University of Miami School of Law and graduated in 2019, according to his LinkedIn. He appears to specialize in the music industry, having worked in the legal department at Sony Music Entertainment for nearly three years before moving on to the Music Product Counsel at TikTok.
Meanwhile, Caitlin seemingly left the acting world after School of Rock. She graduated with a Bachelor of Arts in Journalism and Public Relations from The Walter Cronkite School of Journalism and Mass Communication at Arizona State University in 2013. However, she later became an OBGYN sonographer and an advocate for endometriosis patients. Angelo has been by her side through it all.
“3 years, 2 degrees, and 1 big apple. Making moves!” she captioned an August 2019 photo with her man from her graduation from Nova Southeastern University.
In 2021, Caitlin shared a photo of Angelo sitting by her side at the hospital.
“Happy Endometriosis Awareness month! It’s been 4 weeks since my second laparoscopic endometriosis excision surgery. I can’t thank Dr. Seckin, Dr. Goldstein, and the @seckinmd team enough for their attentive care and thoughtfulness throughout the entire process,” she wrote. “And, of course, couldn’t have done it without @angelo_massagli waiting on me hand and foot during my two weeks of bed rest!”
