New York, New York
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Gabriella and Jack’s West Village engagement session was the perfect reflection of their relationship — full of laughter, love, and nearly a decade of memories together.
High school sweethearts, these two first started dating in January of 2016. Gabby jokes that she made the first move — after all, Jack was a sophomore and she was a senior, and she wasn’t about to let him miss their deeper connection. Nearly ten years later, their bond has only grown stronger, built on countless milestones, moves, and adventures shared side by side.
Their proposal story is one for the books. After moving in together in October 2024, Gabby had started to gently (or maybe not so gently!) nudge Jack about when he planned to propose. She thought she had it figured out — sometime in early 2026 — but Jack had a surprise up his sleeve. On May 29, 2025, what began as a casual dinner with his best friend turned into the most unforgettable night.
Despite a rainy day, Gabby insisted on walking 45 minutes through the humidity to their restaurant in Jersey City. When they arrived, a street performer began playing Taylor Swift’s “Love Story” (a surprise Jack had arranged just for her). The music shifted to Lukas Graham’s “Love Someone,” their song since the very beginning, and Jack got down on one knee. With their families waiting nearby to celebrate and a photographer capturing it all, it was the perfect, heartfelt proposal — frizzy hair, Apple Watch, and all.
Now living in Jersey City, Gabby and Jack love everything from trying new restaurants to cooking meals together, turning everyday tasks into meaningful moments. The West Village has always been a special place for them, and wandering its charming streets for their engagement photos was a natural fit. From quiet corners to lively sidewalks, their session felt like a true celebration of who they are — partners, best friends, and soon-to-be husband and wife.
