This past fall I had the joy of planning what started as a styled shoot, and turned into a surprise engagement for my youngest brother. I had approached Kyle and Leo about doing a shoot because they are such dapper gentlemen, and well, I needed more photos of dapper gents! Then on a trip to RI over the summer, Leo mentioned over many glasses of wine that he would love to propose to Kyle soon, and wanted my help. We tossed around a few ideas, and then I thought of how amazing it would be to do at our shoot. They would already be dressed up, and I could turn the styled table into a celebratory dinner.

I got to work planning the shoot, with input from Kyle on what he would love if this were his wedding. Spicer Mansion in Mystic, CT was the perfect setting, and I loved working with the masculine tones in the blue salon. I incorporated velvet, dark floral napkins, and black tapers (which were definitely outside my usual style, but so fun).

We then decided we would head to the Stonington Harbor Lighthouse in Stonington, CT for the proposal. We told Kyle that we were going to photograph a pretend “first look,” and that he needed to turn around. Connie from Constance Schiano Photography was telling him that she wanted to take a picture of him with Leo walking up behind him. Meanwhile, Leo was actually getting down on one knee! I was watching all this unfold, and it took everything in me not to start jumping up and down.

We finished up with some engagement photos by the water, and then headed back to Spicer Mansion. What Kyle also didn’t know, was that we organized for my immediate family and his best friend to be there when we returned. After another surprise, and so many celebratory hugs, we sat down to an intimate dinner at the table I designed. A styled shoot is always special, as it is a chance to flex our creative muscles. But getting to organize and witness this proposal made me realize how truly amazing my job is.

Participating Vendors:

Photography – Constance Schiano Photography

Calligraphy – Nob Hill Jane

Tabletop – Petals and Plates

Linens – Nuage Designs

Florals – Floral Designs by Justine

Tuxes – The Black Tux

xo Jenn


Styled Shoot Turned Surprise Engagement


As a Connecticut wedding planner, Jennifer specializes in home tented events, as well as weddings at historic venues,
wineries, and by the shore, serving clients all over New England.


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