Swimsuit

2023 SI Swimsuit Rookie Mady Dewey Announces Engagement

The Swim Search winner shared the most adorable Instagram post featuring her fiancé, Jack Hillman.

Ananya Panchal

Mady Dewey

Mady Dewey.

Congratulations to our favorite tech entrepreneur, Mady Dewey! The 2023 SI Swimsuit rookie just got engaged and we’re totally over the moon for her and fiancé Jack Hillman.

The 27-year-old’s longtime boyfriend popped the question in an adorable and intimate way and the model announced the news on Instagram earlier this week.

“our spot, just us, forever 🥹overwhelmed with love and gratitude for you, this moment & this life we’ve built together. LET’S GET MARRIED @jt_hillman !!!!!!! 💍,” the Swim Search alumna, who won the open casting call last year, captioned the carousel she shared on Oct. 31.

Mady Dewey

Mady Dewey was photographed by Ben Watts in Puerto Rico. Swimsuit by AANOUKIS Swimwear. Hat by Aviator Nation.

“MY FAVS I LOVE YALL,” fellow 2023 rookie Sixtine commented.

“Congrats!!!! Such a beautiful couple! & a gorgeous ring! 😍💍 so excited for you!” model Nicole Petrie wrote.

“Just the best news in the world!!!! Can’t wait to see what forever looks like on you 🥹,” one friend gushed.

“Raising a glass to the best couple 🙌🏼 So excited for you both and this next chapter 💜,” another chimed.

The post began with the sweetest silhouette video of Hillman getting down on one knee and pulling out a ring. The couple embraced for a few seconds, kissed and then Dewey ran toward the camera with a huge smile on her face.

The Southern California native, who now lives in San Francisco with Hillman, also included more selfies from the sunset proposal, throwback pics and a gorgeous view of her brand new ring.

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Ananya Panchal
ANANYA PANCHAL

Ananya Panchal is a writer on the Lifestyle and Trending News team for SI Swimsuit. Before joining SI Swimsuit in 2022, she worked at Bustle, the San Francisco Chronicle and the TODAY Show. When she is not writing or doom-scrolling on social media, Panchal can be found playing sudoku, rewatching One Tree Hill or trying new restaurants. She's also a coffee and chocolate (separately) enthusiast. Panchal has a bachelor’s in communications and journalism from Boston University.

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