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June 4, 2019

Boston Seaport Engagement Session | Jessica, Matt, & Dempsey Boston Engagement Photographer

This Boston Seaport engagement session is definitely one of my favorite engagement sessions of all-time! I love shooting at the Seaport because of its’ iconic Boston views. When this couple said they met on a cruise from Boston to Bermuda, shooting at the cruise terminal and then the Harborwalk was the perfect combination for their engagement session. Plus, when you add in their adorable black lab, Dempsey, it really doesn’t get much cuter than that!

I first met Jessica and Matt at the first ever Christmas in the City mini sessions I hosted two years ago with my good friend Christina of Tails ‘N Sails. I could tell back then what an awesome couple they were and then I had the chance to meet Jessica’s immediate family for a shoot last year. Meeting her sisters, parents, and all three of their gorgeous black labs was so much fun. So when Jess and Matt got engaged and reached out about being their wedding photographer, I was so EXCITED! I already can’t wait to celebrate with all of them next year. June 2020 is going to be a great month! 🙂 

I love working with couples like Jessica and Matt. They’re so down-to-earth, fun, and the epitome of go-with-the-flow. As soon as we got out of the car to start their session, it started lightly raining, but it didn’t bother these two at all. We shot right through the rain, which only lasted a few minutes, and then it was clear skies for the rest of the session! Also, how cute is Jessica’s dress? Slightly obsessed with it! 

I loved so many shots from this session and don’t even get me started on how cute Dempsey was looking in his Tails ‘N Sails sear sucker scarf! We captured so many beautiful portraits of Dempsey by himself and with his parents thanks to my go-to girl, Danielle from For The Love of Paws. If you want your dog at your wedding, engagement session, family session, etc, she’s LITERALLY THE BEST! During this session alone, she helped Dempsey pose like a model, sweet talked security guards more than once, and went out of her way to make sure that wherever we parked illegally was going to be ok. Danielle is such a rockstar and I can’t recommend her enough! Scroll to see how her magic with dogs came to life in the photos below! So so excited that she’ll be joining me at Jess and Matt’s wedding next year! 🙂 

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