Newly engaged couples…if eating dessert and strolling through your favorite neighborhood in Boston (in this case, the North End) sounds like your kind of engagement session, let’s talk.

I already liked these two, but when Jake & Diana said this is what they wanted to eat cannolis in the North End for their engagement pictures, I kind of fell head over heels for them! #mypeople

But wait… It. Gets. Better. They brought ME cannolis, too! Yep, that’s plural – not one, but two cannolis. And I’m smitten.

These two are super organized, and sent me a detailed map before our session with the areas they loved, even with a “outfit change” location incorporated! First stop was on the greenway. Diana is an architect so Boston’s skyline was the perfect backdrop. And that light!

Diana & Jake light up when they’re together and have such chemistry. It was easy to see why they’re madly in love.

From the greenway, we headed into Boston’s North End to North Square Park, which is where they spent part of their first date. Here, the three of us dove into the cannolis…there’s a bit of rivalry, where Jake is Team Modern Pastry and Diana is Team Mike’s Pastry. I’m still undecided. I should probably do more research, and I’m sure Ben will happily join me on the quest to determine the winning cannoli.

Finding lovely little pockets in the city…

J+D, I had the BEST time with the two of you and am so excited for your wedding Boston Marriott Long Wharf next summer. Thank you for inviting me into your world, and even more for the cannolis!! xoxo.

Want to see more Boston engagement pictures? Check out Emily & Chris’s Boston Public Garden and Marina Bay session here!