Some love stories begin with a grand romantic gesture; Ariana and Tom’s began with a piece of friendly advice that was promptly ignored. When a mutual friend introduced them, she warned Tom not to “hit on my roommate.” Yet, one effortless first date near Washington Square Park led to late-night city adventures, countless shared meals, summers at the Jersey Shore, and travels around the world together. Nearly five years later, these two are planning a winter wedding at the elegant Pleasantdale Chateau—where the crisp air outside will make the warmth of glowing fireplaces, shared cocktails, and joyous company feel all the more magical.

For their engagement session, we wanted to capture something close to their hearts—home. Hoboken has been the backdrop of so many of their everyday moments, and it was the perfect place to tell this chapter of their story. We approached this session as a true collaboration. Since Ariana and Tom know their neighborhood better than anyone, they led the way—guiding me to the spots that hold meaning for them and capturing Hoboken through their own lens. Ariana stepped naturally into the role of art director, styling moments with effortless charm

We began at the local farmers market, Ariana and Tom laughed and teased each other over the best seasonal veggies, stopping to admire the vivid reds, greens, and golds of the produce stands. Ariana cradled a bundle of fresh blooms in her arms—flowers destined for the picnic we’d end the day with—while Tom carried their market finds with a grin. The scene was lively and full of color, yet their connection made it feel like the rest of the world had faded into the background.

Wine & Oysters at Their Favorite Spot

From the market, we wandered to one of their favorite haunts: a cozy seafood restaurant known for its sustainably sourced local oysters. With the late afternoon sun spilling over the sidewalk, they toasted with glasses of crisp white wine and shared a plate of briny perfection. In between bites, there were easy laughs and soft glances—the kind of moments that feel stolen from time. Watching them here, in a place that clearly feels like home, was like peeking into a page of their everyday love story.

Timeless Charm at Hoboken Terminal

Our next stop was the historic Hoboken Terminal—a true architectural gem. Since its opening in 1907, this Beaux-Arts beauty has welcomed travelers with its soaring arched windows, copper-clad clock tower, and intricate ironwork. Inside, the grandeur of the vaulted ceilings and sweeping staircases gave their portraits a cinematic quality. They moved through the space with quiet ease, their laughter echoing softly against the polished marble and dark wood benches. It felt like we’d stepped into a classic love story, set in the heart of a place that has witnessed countless arrivals and goodbyes.

Sunset Picnic at Pier A Park

As the sun began to sink, we wandered to the lively Pier A Park, the lush stretch of green just steps from the historic Hoboken Terminal. Picnic basket in hand, Ariana styled the scene with effortless charm—arranging their farmers market flowers and favorite treats before slipping off her shoes and settling in beside Tom. The Manhattan skyline shimmered across the Hudson, its lights beginning to twinkle against the soft evening haze. They lingered over wine, shared bites, and watched the city change with the light. It was the kind of day that felt perfectly, unmistakably Hoboken—two people completely at ease, wrapped up in each other and the place they call home.