Sheridan & Shail’s Romantic Engagement Session in the Heart of Boston

Boston is gorgeous city, full of rich history and iconic architecture. It’s also an incredibly romantic city full of happy couples taking advantage of all Boston has to offer, from dinner in the North End to museum hopping. When Sheridan and Shail had expressed interest in doing their engagement photos at the Boston Public Library, I couldn’t wait to begin working with them because I have been longing to revisit the library for another photoshoot. Our session in the library ended before it really got started, unfortunately, but as an experienced photographer I had multiple options to quickly provide my couple with as strong alternatives. Sheridan and Shail’s engagement session took us from the beautiful Boston Public Library to the bustling Newbury Street and ended at the always incredible Boston Public Gardens. If you are planning your own engagement photography session in Boston, continue reading for some helpful tips and tricks to pulling off a successful session.

A happy couple admiring the Boston Public Library's beautiful architecture. They are standing in front of a grand wooden door and she is hugging him from behind. Photography by Mike Indi.

First Stop: Boston Public Library

My wife and I drove down from Manchester to Boston, which took about an hour, and parked at the Boston Commons Garage. We had a little bit of a walk to the Boston Public Library, but it was a gorgeous day and I was able to scout out a few back-up locations on the way. Sheridan and Shail had taken the train into the city early and got a chance to explore the iconic library before we arrived. We met on the front steps and we were excited to begin their engagement session, but we were met with several challenges. The trickiest part about engagement photos in Boston is dealing with the crowds. I have been photographing Boston since my first week with a camera and somehow the city seems busier and busier every time I’m there. Large crowds make it difficult to communicate and can make the couple uncomfortable posing in front of a crowd.

A gorgeous couple dancing together in front of a grand fireplace at the Boston Public Library. Incredible art work is painted above them. Photography by Mike Indi.
A laughing couple sitting on a wooden bench at the Boston Public Library. They are sitting under an antique light fixture. Photography by Mike Indi.
A gorgeous couple dancing together in front of a grand fireplace at the Boston Public Library. Incredible art work is painted above them. Photography by Mike Indi.

I had just gotten my settings dialed in when we witnessed a bride and groom getting kicked out the the library with their photographer. We had both confirmed online that photography was permitted and I heard their photographer mention that to the security guard, but that was not the case. We didn’t stand out, probably because Sheridan wasn’t in her wedding dress, so we were able to sneak off a few photos, but sure enough we had the same conversation with the security guard as well ten minutes later. Luckily, Sheridan and Shail were happy to explore alternate locations for photos. Now, we were still able to utilize the steps out front of the library, which was better than nothing, and used the stunning architecture as a backdrop for their engagement photos.

A happy couple walking along a ledge outside Boston Public Library. Photography by Mike Indi.
A gorgeous couple sharing an intimate moment outside the Boston Public Library during their engagement session. Photography by Mike Indi.
A gorgeous couple sharing an intimate moment outside the Boston Public Library during their engagement session. Photography by Mike Indi.
A gorgeous couple sharing an intimate moment outside the Boston Public Library during their engagement session. Photography by Mike Indi.
A gorgeous couple sharing an intimate moment outside the Boston Public Library during their engagement session. Photography by Mike Indi.
A gorgeous couple sharing an intimate moment outside the Boston Public Library during their engagement session. Photography by Mike Indi.

Next Stop: Newbury Street

Once we had finished with photos at the Boston Public Library, we took a short stroll over to Newbury Street to continue Sheridan and Shail’s engagement session and to go on a little adventure. We took some time to get to know each other and discuss some of the details of their wedding next year. My wife and I were able to connect with them because we got married at the same location (Searles Chapel) 5 years ago. As we wandered up the street we found so many great spots for photos, it can become overwhelming with the endless options for photos in Boston. We continued down the street towards Boston Public Gardens, which I thought would be the perfect place to end their engagement session.

A gorgeous couple looking into each other's eyes and resting their foreheads together. Engagement photos on Newbury Street in Boston. Photography by Mike Indi.
A gorgeous couple sharing an intimate moment during their engagement session on Newbury Street in Boston. Photography by Mike Indi.
A happy couple showing off their engagement ring during their engagement session on Newbury Street in Boston. Photography by Mike Indi.

Final Stop: Boston Public Garden

By the time we reached the breathtaking Boston Public Gardens, Sheridan and Shail had grown into naturals. Like so many couples, Sheridan had “warned” me that they would need a lot of work. I reassured her that it’s not their job to know how to model. Instead, I provide my couples with simple prompts, which are mostly open to interpretation. My goal is to keep them moving, focusing on each other, being in the moment, and most importantly, laughing through the awkward moments.

A gorgeous couple walking through Boston Public Gardens holding hands and smiling during their engagement session. Photography by Mike Indi.
A lovely couple dancing during their engagement session at Boston Public Gardens. Photography by Mike Indi.
A gorgeous couple walking through Boston Public Gardens while holding hands during their engagement photography session. Photography by Mike Indi.
An epic photo of a gorgeous couple sitting on a rock in Boston Public Gardens during their engagement photography session. Photography by Mike Indi.

Sheridan and Shail’s engagement session in Boston was a fun little adventure around my favorite city. From the historic charm of the city to the radiating chemistry between the happy couple, every photo I captured perfectly showcases their love story. As our session came to a conclusion, we chatted about their wedding until we said our good-byes, for now. These two are currently planning their gorgeous wedding which will be held at Searles Chapel, October 2024! If you are planning a wedding in 2024 or 2025, now is the perfect time to reach out and book your own engagement session.


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