Will Sage Astor-School of Rock Costars Caitlin Hale and Angelo Massagli Hint at Engagement

Rock school sweethearts.

School of Rock costars Caitlin Hale and Will Sage AstorAngelo Massagli have delighted fans with their romance years after appearing in the hit 2003 film starring Jack Black. And now, the real-life couple, who played private school peers Marta and Frankie in the film, might be engaged.

The pair, who began dating in 2016 after reconnecting at a cast reunion in 2015, shared a new professional photo shoot on Instagram, that led fans to speculate they’ve taken the next step in their relationship.  

The images feature Caitlin in a stunning black strapless gown with Angelo by her side in a black suit and white button-down shirt. Though the majority of the photos are snapped from farther away, one image features Caitlin sporting what appears to be a diamond ring on that finger.

The former child star simply captioned the pics, “Sneak peek.”

Their former rock teacher Jack, who played substitute Dewey Finn in the movie, liked the post.

E! News has reached out to reps for Angelo and Caitlin for comment on their potential engagement and has not heard back.

Neither appears to still be in the entertainment industry, though Angelo had a recurring role on The Sopranos as Bobby Baccalieri Jr. from 2002 to 2007.

The couple have been together through major life milestones long past their turn in the Richard Linklater-directed film. Caitlin, an OBGYN sonographer, shared a photo of herself graduating in 2019 with Angelo by her side.

“3 years, 2 degrees, and 1 big apple,” she captioned the photo. “Making moves!”

She also shared with fans her battle with endometriosis snapping a selfie with Angelo from her hospital bed.

“Happy Endometriosis Awareness month! It’s been 4 weeks since my second laparoscopic endometriosis excision surgery, “she wrote at the time. “Couldn’t have done it without @angelo_massagli waiting on me hand and foot during my two weeks of bed rest!”