Bond Girl-to-Be: An Editorial Engagement Session at The Red Fox with Caroline & Taylor
“I audibly screamed. They are the coolest photos I have ever seen. He killed.”
Not every engagement session starts with a park, a waterfront, or Boston's cobblestone streets. Sometimes it starts in an empty restaurant before dinner service, with a camera, a flash, and an idea. That’s exactly was Caroline and Taylor wanted.
One of my favorite parts of being a Boston engagement photographer is when couples come to me with a vision that feels entirely their own. This session was especially meaningful because the bride-to-be was one of my OG clients, someone who has been part of my photography journey almost since the beginning. This October, I'll also be photographing their intimate wedding at The Alibi inside The Liberty Hotel as their Boston elopement photographer, making this engagement session the perfect way to kick off their wedding season.
The vision was simple: editorial, cinematic, a little moody, and above all, fun.
We met at The Red Fox in Boston's North End before the restaurant opened for the evening. While we waited, I wandered the space taking a few solo portraits and using the quiet restaurant as a chance to experiment with both on-camera and off-camera flash. Having spent years working in the service industry before becoming a photographer, it was fun being back in that familiar environment, and it also reminded me to stay conscious of the staff getting everything ready for the night ahead.
Once we were all together, the session took on a life of its own.
We bounced between velvet booths, the bar, hidden corners, and dramatic curtains, chasing whatever caught our eye next. The goal was never perfect posing. It was creating images that felt stylish without feeling forced. We leaned into the editorial vibe while making sure to keep one very important detail in focus: an absolutely massive engagement ring that seemed to catch every flash perfectly.
At one point the bartender looked over and asked, "Is it too early for a drink?"
With newfound cocktails in hand, the energy shifted again. One idea led to another, and before long we were photographing on the restaurant's tiger print flooring while showing off a brand-new tattoo of her future last name: BOND. Naturally, the Bond Girl jokes started almost immediately.
Some of my favorite photographs come from moments exactly like these. Not because they were planned, but because everyone was comfortable enough to throw ideas around and see what happened. That's always the goal. The best Boston engagement photography isn't about recreating Pinterest boards or checking poses off a list. It's about creating an experience where couples feel comfortable enough to be themselves and trusting the creative process along the way.
This session was also a chance for me to continue pushing my own creativity with flash photography. I love experimenting with light, especially when I have couples who are excited to create something together rather than simply stand in front of the camera. Every room offered a new challenge, and every challenge became another opportunity to make something unique.
By the time we wrapped up, it felt like we'd accomplished exactly what we'd set out to do. The photos are editorial without losing their personality, cinematic without taking themselves too seriously, and completely reflective of who these two are. I can't wait to see Caroline and Taylor again this October and continue telling their story as their Boston elopement photographer.
