This ‘Jewish Matchmaking’ Star Just Got Engaged!!

Mazel tov, [name redacted for spoilers]!

Light spoilers for “Jewish Matchmaking” ahead.

Fay Brezel and Shaya Rosenberg were far-and-away my favorite couple on “Jewish Matchmaking.” The pair, who are both part of the Brooklyn Orthodox Jewish community, clicked immediately on their modest first date. “They had electric chemistry on the screen,” matchmaker Aleeza Ben Shalom gushed to me recently. “They were laughing — you could see the look in their eyes and the humor and the banter. The banter was… it was so delicious.”

But it wasn’t bashert. After three dates and a conversation with dating mentor Dr. Jack Cohen, Fay and Shaya amicably decided to see other people. The problem? Their level of religious observance didn’t quite align. (Fay wants a man whose level of religiosity is equal to hers or higher, and Shaya, while he does study Torah every morning, adorably describes himself as “not a learning boy.”)

However, we still have an exciting happily-ever-after to share! This week, Shaya got engaged!!

Shaya Rosenberg Jewish Matchmaking Engaged
Photo by Chesky Ostreicher/Sky Studio New York (@skystudiosny)

Right before Sukkot, Shaya met his now-fiancée Hoovee, who comes from an ultra-Orthodox background. “I think half the community tried setting us up,” he told Hey Alma. After flying to Israel for the holiday, Shaya met Aleeza for dinner in Tel Aviv, telling her all about Hoovee and how he thought she might be the one. “She guided me and advised the best course for dating successfully. And it worked!”

Fast forward a few months, and Shaya began planning his proposal timed to the release of “Jewish Matchmaking.”

Before a watch party organized by his friends, Shaya took Hoovee to Starbucks and then Teraza Restaurant Lounge in Coney Island — replicating their first date. (Naturally, this was preceded by a visit to Shaya’s rabbi, who gave them a blessing and hinted that Shaya should propose already.)

“We walked into the bar and took a seat in front of a black curtain that looked like the place was under construction. With her back facing the curtain, I told her how amazing the last few months had been and how I couldn’t have hoped to have met someone more perfect than her,” Shaya explained.

He went on, “After a few moments, the song we first heard playing in Starbucks seven months earlier [‘Love Story’] started playing. I stood up with her and walked her to the center of the black curtain as Taylor Swift sang, ‘He knelt to the ground and pulled out a ring, and said, ‘Marry me, Juliet,’ I did the same while the black curtain dropped revealing a 20-foot-wide, 4-foot-high ‘Marry Me’ sign with an 8-foot heart-shaped rose arch. The ceiling was filled with pink and white balloons and the floor covered with rose petals and candles. It’s all been a blur since she said ‘Yes’ to making me the happiest man in the word. But this is matchmaking done right!

“Did I mention she’s a balaboosta and a great chef?” Shaya concluded.

Photo by Chesky Ostreicher/Sky Studio New York (@skystudiosny)

I am absolutely kvelling.

You can watch the beautiful proposal here:


Love is a beautiful thing, and being able to witness it firsthand is truly a blessing. I feel incredibly grateful for the opportunity to help create & capture those special moments of love and appreciation between two people. From setting the perfect mood and vibe to choosing just the right color tones, I love being able to help make those once-in-a-lifetime moments unforgettable. Thank you to all of my clients for trusting me to help set the vibe & capture your cherished memories and freeze them in time forever. It’s truly an honor to be a part of your journey. #love #appreciation #lighting #design #proposal #couples #eventplaninng #eventproduction #video #love #marriage #onceinalifetime #cherishedmemories

♬ Love Story (Taylor’s Version) – Taylor Swift

Mazel tov, Shaya and Hoovee!

Evelyn Frick

Evelyn Frick (she/they) is a writer and associate editor at Hey Alma. She graduated from Vassar College in 2019 with a Bachelor of Arts in English Literature. In her spare time, she's a comedian and contributor for Reductress and The Onion.

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