Jessie first reached out to me on Reddit of all places. She and Lucas were looking for a photographer to document their personalized film engagement photos. They were drawn to the unforced, in-between moments that film engagement photos create. We began planning personalized film engagement photos in Western Massachusetts, focusing heavily on what makes their relationship so unique.

Their vision aligned perfectly with my passion for capturing honest, unfiltered moments. They wanted an experience that felt entirely like them—no stiff poses, no unfamiliar backdrops. Just them, enjoying each other’s company in places that hold their fondest memories.

We crafted an afternoon that celebrated their shared history, their individual passions, and the beautiful community that surrounds them. The photographs are a testament to the power of a personalized photography experience, capturing their day beautifully through the authentic lens of film.

A Deeply Personalized Photography Experience

When it came time to plan their personalized film engagement photos, we bypassed the standard public parks and headed to the spaces that meant the absolute most to them. We spent our time exploring the area around Luke’s family estate, right where he grew up.

Documenting their engagement inside his parents’ gorgeous mid-century modern home allowed them to exist as they normally would together. No goofy prompts or awkward moments in front of the camera. One of my favorite moments of the entire session was with Jessie. She brought along a beautiful sweater she had been knitting for Luke. They sat together on the couch, had some coffee while Luke read, and Jessie knitted. It was a really sweet way to personalize the shoot through with things they do in their day-to-day lives. They told us they love to sit and cuddle on the couch together every day. We also spent time at his sister’s nearby farm.

A Love Story Rooted in Western Massachusetts

Jessie had just moved to Western Mass to start her demanding medical residency. Eager to make friends outside the hospital walls, she joined Hinge. That decision led her to match with Luke, and their story quickly unfolded.

Their first date was active and unconventional. They met up for a community CrossFit class, sweating through a workout before grabbing coffee at Shelburne Falls. They followed that up with a long, peaceful walk in Easthampton. The connection was immediate and undeniable. The very next day, they met again to visit the beautiful Peace Pagoda and share a quiet lunch at the Book Mill. To this day, they consider that afternoon their first real date.

Medical residency is notoriously taxing, and Jessie soon started her “night float” rotation. For four weeks, she worked entirely through the night, with only Saturdays off to recover. During this exhausting time, Luke became her rock. He would text her every single morning to see if she had survived the shift. He brought her warm meals and took her on gentle walks before she had to head back into the hospital for another grueling night. Those quiet, supportive moments amidst the chaos of her schedule became the foundation of their relationship together.

Jessie and Luke share a love for the outdoors. Jessie finds her peace in running, pilates, and yoga, while Luke spends his downtime lifting, fishing, and hunting. Together, they love trail running at Whiting Reservoir near Mount Tom. We made sure their personalized film engagement photos reflected this adventurous spirit. We wandered through the public lands surrounding the family estate, capturing their love for the outdoors. The rustling leaves and the cool Western MA breeze provided the perfect, rich environment for their portraits.

Personalized Film Engagement Photos

Wondering what it’s like and what’s included in our personalized film engagement photos? We’ll walk, eat, talk, hang, and make some damn good film images while we’re at it. These sessions come with full-day flexibility and plenty of film to capture whatever unfolds. Let’s get into the different packages we offer and how we can customize them for you!

Boston Film Engagement Photos

*anything within 1 hour of Boston

This is where it all began for us, and where so many of our couples have built their lives. Your Boston engagement session might mean returning to the neighborhood where you fell in love, revisiting the spot where you got your first apartment, or simply walking the streets that feel like home. These sessions are slower, more intentional, and all about capturing you as you are. Whether that’s sharing soup dumplings in Chinatown or dancing barefoot in your backyard.

New England + NYC Film Engagement Photos

*anything within 4 hours of Boston

These are for the folks craving something a little different: a weekend road trip, a city you haven’t explored together in a while, or a quiet cabin in the woods. Maybe we’re capturing the proposal you’ve been planning for months, or maybe it’s just time to make some damn good art out of the way you love each other. We’ll pack up our cameras, hit the road, and co-create a session that feels like it belongs to your story. From bonfires on the beach to brownstone stoops in Brooklyn, if we can drive there and back in a day, we’re in.

Beyond

*anything 4+ hours from Boston

Whether it’s home for you or somewhere new for all of us, we love documenting couples in places that mean something. We’ve photographed sessions in Miami, California, Québec, Thailand, and beyond. Sometimes we’re meeting you in your hometown, other times we’re all traveling for the sake of adventure. Either way, we’re in. If we’re photographing somewhere neither Javi nor I speak the primary language (outside of English, Spanish, or French), we like to collaborate with a planner or point person who knows the area and speaks the language. It keeps everything smooth and lets us stay fully focused on telling your story 100% on film.

Personalized Film Engagement Photos

Cherish Every Memory on Film

If you are an engaged couple in the Boston area or Western MA looking to capture your day beautifully, I would love to hear your story. Your wedding and your engagement should be a true reflection of who you are. Our comprehensive packages provide a personalized photography experience that emphasizes quality and classic film aesthetics. Reach out here to start planning your personalized film engagement photos!

Castillo Holliday Photo And Film Team l Film Engagement Photos

Photography: Castillo Holliday Photo + Film | @castillohollidayphotoandfilm