Jake & Jayme’s Surprise Proposal at Winter Island Park

 

It’s always a privilege to capture important milestones for a family, and Jake’s family is one I’ve known for years. I photographed his parents’ wedding in the early ’90s and later, his Bar Mitzvah. So, when Jake reached out to me about photographing his surprise proposal to Jayme, I couldn’t have been more excited. Jake and Jayme have been together since being high school sweethearts, so I knew this session would be very special. 

We had a blast planning the secret proposal. Jake’s Mom was in on it, and about two weeks before the proposal date she mentioned to Jayme, “My friend canceled her nail appointment with me! Do you want to go together?” So they got her nails done for the big day. This was just one of many behind-the-scenes schemes.

 

 

Jake and my associate Mike talked at length about the location, time of day, the tides, and the best spot for photos. We decided on Winter Island Park because of the beautiful location featuring both the ocean and the forest. Jake crafted the perfect plan to lure her there.

To quickly block off the day on their schedule, Jake suggested he and Jayme go to Vermont for a weekend visit with friends. As part of the master plan, he told her it was canceled, and had instead arranged for them to meet friends who would pick them up by boat at Winter Island Park for dinner in Gloucester. 

Our plan was to mark the location beforehand with a single rose on the beach, using Winter Island’s iconic lighthouse as the backdrop. Mike and I coordinated the camera angles so we could capture the proposal from two perfect positions. We briefed Jake on how to approach the rose and position the two of them on each side.  

 

 

On the big day, we are ready for action. Jake had one of Jayme’s girlfriends pick out a beautiful dress, and sent us a picture so that when they arrived we could see them from a mile away. We also had a description of their car so we could spot them as soon as they arrived. Mike pretended to be fixing a rack of kayaks, and I blended in as a tourist, taking pictures of the lighthouse and seashells.

As they stroll past us, Jayme has no idea what was about to unfold. Jake leads her to the rose on the beach without missing a beat. He tosses her jacket that was covering up the ring box in his pocket and is down on one knee within seconds. 

 

 

She burst into sheer joy, and in that magical moment, she said yes! After they collected themselves, we spent some time capturing the newly engaged couple around Winter Island. We balanced traditional portraits with photojournalism, capturing the pure emotion of the day.

 

 

After completing the portrait session, we rush back to the fabulous restaurant Finz Restaurant in Salem for yet another surprise! Jake had planned an intimate engagement party with their closest family members. We arrived at the restaurant just before Jake and Jayme, hiding alongside their loved ones in a private room. When the newly engaged couple walked in, they were greeted with cheers, hugs, and tears of joy. 

 

 

We ended the perfect evening by taking family portraits outside Finz at Pickering Wharf with the historic Friendship of Salem vessel as the perfect backdrop.

AND, we were never caught along the way. 

Being part of such a meaningful moment for Jake and Jayme was an honor, and it’s these moments that remind me why I love what I do.