School of RockStar Caitlin Hale Teases Engagement to Former Costar Angelo Massagli with Glam Photoshoot!

Mar. 15, 2025

TCGEAW ROCK ACADEMY THE SCHOOL OF ROCK 2003 de Richard Linklater Angelo Massagli.; Caitlin Hale and Angelo Massagli; School of Rock (2003) Caitlin Hale.Photo:Paramount/Alamy; Caitlin Hale/Instagram; Andrew Scwartz/Paramount

Paramount/Alamy; Caitlin Hale/Instagram; Andrew Scwartz/Paramount

School of Rockstar Caitlin Hale is showing off a new sparkler!

Hale and Massagli could be seen dressed up in formal attire as they posed in front of several monuments in Brooklyn, New York. In the opening photo, the pair smile at the camera as Massagli places a hand on Hale’s waist and she rests her hand on his shoulder.

Angelo Massagli; Caitlin Hale.Alamy Stock Photo; Andrew Schwartz/Paramount

Additional snaps show the pair posing in front of a bridge with New York City in the background and laughing together while on a skywalk. She also shared a sweet photo of the pair leaning into each other as they had their arms around each other.

The actress wore a black strapless dress for the snaps with her hair styled up. Notably, her left hand featured a large sparkling diamond ring. Massagli wore a suit jacket with matching black slacks and shoes.

“Sneak peek 😘,” she captioned the photos.

The actors began dating in 2016, Massaglitold Inside Edition, revealing that they hit it off over a decade after the film released when he learned Hale was moving to Florida, where he was living at the time.

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“We have a group chatwhere all theSchool of Rockkids, we just hit each other up whenever someone moves somewhere new or is doing something different,” Massagli said, noting that the two then met up for lunch, dinner and drinks.

“The rest is history,” Hale said, adding of their relationship, “This is locked down. Yes. This is it.”

Massagli told the outlet that he knew there was something special about Hale from the first time they met during auditions for theJack Black-led film when they were just 10 and 11 years-old, respectively, at the time.

“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,” Massagli recalled. It was excellent.”

Since then, Hale has documented several special moments the pair shared together on social media, including Massagli supporting her through hergraduationfrom Nova Southeastern University and at her bedside following herlaparoscopic endometriosis excision surgeryin 2021.

source: people.com