Anna + Ian | A Downtown Engagement Session |Boston, Massachusetts

This winter has been a whirlwind of various weather. And despite the fact just exactly a week prior to this session it was 70* and there was hardly any snow, the skies ended up dumping just a few inches and by the time last Sunday came, it was back to being chilly with just enough wind to make the air bite your skin.

When Ian and Anna had suggested that we do their session in downtown Boston, I just knew it was going to be epic!! I have never really done city sessions before — aside from the small city like setting in downtown Portsmouth near the gardens. And with me and my husband being big Boston fans (KJ thinks Boston is the center of the universe lolol), we knew this was a perfect opportunity for me to shoot there and make a family day out of it!!

We met at Acorn Street, which if you are like me and never have heard of the infamous Acorn Street, it is the cutest and most quaint New England street I have ever seen. So much so that just while we were there for about 30 minutes, it was swamped with tourists taking selfies. It was SUCH a cute backdrop for photos, and I truly hope to get back there for another session in the Spring or Summer because I am just in love with that area!

Ian and Anna are incredibly sweet! It literally felt like I had known them for a while and it was like old friends catching up. It was easy to talk and laugh with them, and with Ian being so sweet and goofy the whole time, I felt like it made my job capturing them two on camera incredibly easy!! I feel like I say that a lot… but they were just so amazing!!

Their wedding day, though on Halloween, will not be featuring costumes. But I simply cannot wait for their big day!! Both will have family traveling for the wedding (potentially on big party buses if the weather somehow doesn’t cooperate) and I have a great sense that it is going to be just an incredible event!

Anna and Ian — thank you both SO much for trooping through the wet snow, slipping a little bit, dealing with the people passing by, holding those poses like champions and handling my loud self getting shooshed by someone on Acorn Street!! Enjoy some of my favorites ❤

xo – Jess

They took off their jackets for a quick “outfit change” and they rocked it despite how cold it was!!
This is a top favorite!!!
And this one!!!
I looooove Anna’s dark curly hair and her eyes are GORGEOUS!!!!

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