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‘School of Rock’ Cast Reunites for Caitlin Hale and Angelo Massagli’s Wedding

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‘School of Rock’ Cast Reunites for Caitlin Hale and Angelo Massagli’s Wedding

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.

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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.

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“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.’”

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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.)

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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.

Binge more Vows columns here and read all our wedding, relationship and divorce coverage here.

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.

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“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.”

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“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.’”


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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Fashion’s Climate Reckoning Is Just Getting Started

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Fashion’s Climate Reckoning Is Just Getting Started
From dangerous heat on factory floors to flooding across sourcing hubs, climate risks are catching up with fashion’s supply chains. While new recycling initiatives attempt to scale to address the industry’s waste and emissions problem, easing regulation in Europe raises questions about the path forward heading into 2026.
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The 2025 Vibe Scooch

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The 2025 Vibe Scooch

In the 1998 World War II film “Saving Private Ryan,” Tom Hanks played Captain John H. Miller, a citizen-soldier willing to die for his country. In real life, Mr. Hanks spent years championing veterans and raising money for their families. So it was no surprise when West Point announced it would honor him with the Sylvanus Thayer Award, which goes each year to someone embodying the school’s credo, “Duty, Honor, Country.”

Months after the announcement, the award ceremony was canceled. Mr. Hanks, a Democrat who had backed Kamala Harris, has remained silent on the matter. On Truth Social, President Trump did not hold back: “We don’t need destructive, WOKE recipients getting our cherished American awards!!!”

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How to have the best Sunday in L.A., according to Keiko Agena

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How to have the best Sunday in L.A., according to Keiko Agena

Keiko Agena likes to create moments of coziness — not just on Sundays, but whenever she possibly can.

“Oh, there’s my rice cooker,” she says when she hears the sound in her Arts District home. “We’re making steel-cut oatmeal in the rice cooker, which by the way, is a game changer. I used to have to baby it and watch it, but now I can just put it in there and forget it.”

Sunday Funday infobox logo with colorful spot illustrations

In Sunday Funday, L.A. people give us a play-by-play of their ideal Sunday around town. Find ideas and inspiration on where to go, what to eat and how to enjoy life on the weekends.

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The 52-year-old actor, who played music-loving bestie Lane Kim in the beloved series “Gilmore Girls,” delights in specific comforts like a bowl of warm oats, talking about Enneagram numbers and watching cooking competitions with her husband, Shin Kawasaki.

“It sounds so simple, but I look forward so much to spending time on the couch,” Agena says with a laugh.

It is time that she’s intentional about protecting, especially amid her kaleidoscope of projects. Over the last couple of years, Agena starred in Lloyd Suh’s moving play “The Chinese Lady” in Atlanta, acted in Netflix’s “The Residence,” showcased her artwork in her first feature exhibit, “Hep Tones” (some of her ink and pencil drawings are still for sale), and performed regularly on the L.A. improv circuit. And her work endures with “Gilmore Girls,” which turns 25 this year. Agena narrated the audiobook for “Meet Me at Luke’s,” a guide that draws life lessons from the series, and is featured in the upcoming “Gilmore Girls” documentary “Drink Coffee, Talk Fast.”

She shares with us her perfect Sunday in L.A., which begins before sunrise.

5 a.m.: Morning solitude

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I like to be up early-early, like 5 a.m. I like that feeling of everything being quiet. I’ll go into the other room and do Duolingo on my phone. I am a little addicted to social media, so the Duolingo is not just to learn Japanese, but also to keep me from scrolling. Like, if I’m going to do something on my phone, this is better for me. I think my streak is 146. Shin is Japanese, from Toyama. So I’ve been meaning to learn Japanese for a while. For him and his mom.

Then I’ll do [the writing practice] Morning Pages. I don’t know when I learned about Julia Cameron’s book [“The Artist’s Way”] — probably around 2000. I know a lot of people do it handwritten, but I’m a little paranoid about people, like, finding it after I die. So if I have it on my computer and it’s password protected, I can be really honest.

Then a lot of times, I’ll go back to bed. Shin, as a musician, works at night, and so he wakes up a lot later. So I’ll fall back asleep and wake up with him.

9 a.m.: Gimme that bread

I don’t do coffee anymore because it’s a little too tough for my system, but I’ll walk with Shin to Eightfold Coffee in the Arts District. It’s tiny but very chill. Then we’re going to Bliss Bakery inside the Little Tokyo Market Place. We get these tapioca bread balls. If you make any kind of sandwich that you would normally make, but use that bread instead, it ups the game. It’s life-changing. The Little Tokyo Market Place is not fancy or anything, but it has everything that you would want. There’s Korean food. They have a little sushi place in there. You can get premade Korean banchan and hot food in their hot food section. They also have a really good nuts section. It’s just one big table with all these nuts, just piles and piles.

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10 a.m.: Nature without leaving the city

We’ll go to Los Angeles State Historic Park near Chinatown. I like that place just because it’s very accessible. Like, they have accessible bathrooms and I’m always checking out whether a place has good bathrooms. We call it Flat Park because it’s a great walk. Like, you’re not really out in nature, but there’s a lot of greenery. You can take your shoes off and at least touch grass for a second.

11:30 a.m.: Lunch and TV cooking shows

One of my favorite salad-sandwich combos is at Cafe Dulce in Little Tokyo. A Korean cheesesteak and a kale salad. That’s always like a — bang, bang — good combo. So we might go there or Aloha Cafe, though it’s not fully open on Sundays. But I love it because I grew up in Hawaii. They have this great Chinese chicken salad and spam musubi and other Hawaiian food that is so good.

We’ll bring home food and watch something. Cooking competition shows are my cream of the crop. My favorite right now is “Tournament of Champions” because it’s blind tasting. To me, that’s the best way to do it. “The Great British Bake Off” is Shin’s favorite. He loves the nature and the accents as much as the actual cooking. He just loves the vibe, the slow pace of the whole thing.

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I’m such a TV girl. I love spending time on the couch and eating a meal and watching something that’s appetizing with my favorite person in the world. I’m lucky because I get to do that a lot.

2 p.m.: Browse the aisles

I’ll go to this bookstore called Hennessey + Ingalls. I love art and architecture and design, but you can’t always buy these massive books. But you can go into this bookstore and look at them and it’s always chill.

If I have time, I’ll walk around art supply stores. Artist & Craftsman Supply is a good one. I’ll look at pens, pencils, stickers, tape, washi tape, different kinds of paper, charcoals. In my art, I try to find things that aren’t meant for that particular purpose, like little things in a hardware store that I’ll use it in a different way.

5 p.m.: Downtown L.A. in its glory

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We really love to walk the Sixth Street Bridge. It’s architecturally beautiful and they’re building a huge park over there, so we’ll walk around and check it out, like, ‘Which trees are they planting? Can you see?’ We sort of dream about how it’s coming together. But the other beautiful thing about that walk is that if you go at sunset and you walk back toward downtown, it’s just gorgeous. Los Angeles doesn’t have the most majestic skyline, but it’s so picturesque in that moment.

6:30 p.m.: Cornbread and Enneagrams

I’ll head to the Park’s Finest in Echo Park. It’s Filipino barbecue. It’s just so savory and rich and a special hang. Their cornbread is really good. Oh, and the coconut beef, but I’m trying to eat less beef. They have a hot link medley. Oh my gosh, just looking at this menu right now, my mouth is watering. OK, I’ll stop.

One of my favorite things to do is ask friends about their Enneagram number. So the idea of sitting with friends over a good meal and asking them a bunch of personal questions about their childhood and what motivates them and what their parents were like and what their greatest fear is and then figure out what their Enneagram number is? That is a top-tier activity for me.

9 p.m.: Rally for improv

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Because I get up so early, if 9 o’clock, I’m ready to go to sleep. But I am obsessed with improv, so on my ideal day, there’d be a show to do. There’s this place called World’s Greatest Improv School in Los Feliz. It’s tiny and they just opened a few years ago, but the vibe there is spectacular.

Then there’s another place where my heart is so invested in now called Outside In Theatre in Highland Park. Tamlyn Tomita and Daniel Blinkoff created it together and not only is the space gorgeous — I mean, they built it from scratch — they have interesting programming there all the time. They’re so supportive of communities that are not seen in mainstream art spaces. It’s my favorite place. Sometimes I’ll find myself in their lobby till 12 o’clock at night. The kind of people I like to hang around are the people that hang out in that space.

11 p.m.: Turn on the ASMR and shut down

I am firmly an ASMR girl and I have been for years. I have to find something to watch that will slow my brain down. Then it’s pretty consistent. I don’t last very long once I turn something on. My eyelids get heavy and it chills me out.

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