Surprise Proposal Photography Tips

Planning the perfect proposal is a big moment in your relationship, and choosing to capture it with a photographer makes it even more memorable. In MA, there are so many beautiful spots that provide the ideal backdrop for asking, “Will you marry me?” 

Whether you’re looking for a scenic view, an intimate setting, or a popular landmark, each location brings something special to your story. As a Massachusetts photographer, I’m sharing real stories of couples who said “yes” here in Massachusetts to get the ideas flowing! With a few key details in place, you can focus on the popping the question while I capture the moment! 

Surprise Proposal Photography Tips & Engagement Photos

• Choose a trusted photographer. You want someone who understands how to capture the big moment without intruding on it.
• Coordinate any special elements like flowers, decor, picnic, champagne, or a reservation for a celebration afterward. 
• Select a specific proposal spot. It’s essential to pinpoint the exact location so your photographer can be in place and ready to capture everything. Communication with your selected photographer is key! 
• Plan for more portraits after the proposal. This is the perfect time to capture the excitement of the moment with newly engaged photos.
• Decide on your proposal approach. How will you get your partner ready? Do you need to enlist the help of family or friends? You can go with a cover story like we are doing a “couples photoshoot,” or you can keep it a complete surprise. Either way, we’ll make sure it’s beautifully documented!
• Invite Family or Friends: This is not a must, but decide if you want the moment to be private or to invite family and friends to celebrate after you pop the question! 

Wedding Proposal Ideas At Home

Eric and Brie’s surprise proposal had me sniffling behind my camera! It was a beautiful moment to witness Eric asking Brie to marry him. He worked with The Menta Graze Company and Brie’s mom to set up a beautiful picnic at a family home. The picnic of course included champagne and a charcuterie board! Eric proposed with a ring that Brie has loved since age 11! After the proposal, we took some photos along the water and were greeted with hugs and excitement from their families! 

Surprise Proposal Photography at The House of Seven Gables

Edgar and Daniella were visiting Salem, MA for a week from Los Angeles. Months in advance Edgar reached out to me to plan the perfect proposal for Daniella. After exchanging ideas, we settled on the stunning House of the Seven Gables as the location. Once we had the venue’s blessing, the plan was set in motion.

Edgar cleverly told Daniella he had booked a photo session in Salem, which was the perfect cover, especially since she loves Halloween and Hocus Pocus! When I met them in the lobby, we headed outside for a few warm-up poses. Then, I suggested a fun prompt where they would face opposite directions and turn to each other on the count of three.

As I was setting it up, I quietly checked in with Edgar, and he gave me the thumbs up. When the moment came, Daniella turned around, and her face lit up as Edgar got down on one knee and asked her to marry him! A chorus of “Yes, yes, yes!” erupted, followed by laughter, hugs, and kisses. Afterward, we took some beautiful engagement photos around the Gables and wrapped up the day at Derby Wharf.

Surprise Proposal Photography

Bailie reached out to me about surprise proposal photography in Salem for his girlfriend Katie. He wanted the proposal to be timed with their Halloween visit. Coming all the way from Pittsburgh, they wanted to make this moment unforgettable. After going over a few options, we settled on the picturesque Derby Light Station as the perfect spot! I arrived early and nestled myself among the rocks, trying to blend in as a tourist. I snapped countless photos of the lighthouse and the sailboats in the harbor, eagerly waiting for their arrival. 

When I finally spotted them approaching, I quickly shifted my focus to the couple. A group of tourists kindly offered to take their photo, which turned out to be perfect as they stepped back to give Bailie and Katie space. At that moment, I watched as Bailie reached into his pocket. A collective gasp and hushed “SHH! SHH!” rippled through the crowd as he popped the question. 

Katie’s joyous “Yes!” was followed by hugs and kisses, and the crowd erupted into cheers. Katie noticed me and pointed, looking to Bailie, who nodded proudly, confirming that he had orchestrated this beautiful surprise. After congratulating the newly engaged couple, we explored Salem together taking portraits and just taking in the moment!

Looking to plan a surprise proposal? Reach out to Katlyn Reilly Photography to get started! I would love to help you plan the perfect moment for your partner!