Kyle & Kelsey | South Boston Engagement Session


Kyle’s proposal to Kelsey didn’t go exactly as planned. He had it all set up at their go-to, South End Boston neighborhood restaurant, the Parish Cafe. Kelsey would order a beer at the bar, and the bartender would serve it to her in a mug with the engraved words, “Will You Marry Me?” Except, Kelsey decided on that night of all nights she would order a cocktail instead. Luckily, Kyle made a quick save, and Kelsey still got the mug. Kyle got a yes.

Even if there was a slight hitch in Kyle’s proposal plans, my engagement photo session with this couple was a cinch. They were a photographer’s dream come true: I didn’t have to pose them at all; they are absolute naturals when it comes to getting their picture taken together!

Kyle and Kelsey were such a fun couple to work with. It was so wonderful spending time with them at their gorgeous South End apartment with the amazing roof deck, where they love to entertain, play Scrabble and spend quality time with their dog, Ella. I loved the series of black and white photos taken on their deck. They’re such a fun-loving couple, but these photos really showed the quieter, more intimate side to their relationship.

My favorite images from our time together were taken at the Cafe. They decided to go back to their favorite restaurant where Kyle originally proposed. Kyle even brought along the will-you-marry-me mug. Kyle and Kelsey were truly at home there, so relaxed and comfortable, not caring about anything that was going on around them – all that mattered was being together for such a great session.

Kyle and Kelsey, thank you so much for letting me capture your engagement memories for you. Best wishes on your September 2015 wedding at the Boston Public Library. (And, Kyle, I heard a rumor that you may show off your rapping skills at the reception – I say go for it!)


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    Jackie Ricciardi is a wedding, editorial and corporate photographer, based in Boston, including Worcester. As a full-time photojournalist and photographer, Jackie is available for travel throughout Massachusetts and the Northeast.