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Planning the Perfect Surprise Proposal

When Shiv reached out to me to plan a winter proposal to his girlfriend, Juhie, I was so excited to help his vision come to life. In this post, I want to show you his proposal photos, but also create a mini-guide of things proposers should think about when planning a proposal.

Shiv wanted to propose to Juhie outdoors, in a Bostonian location. He didn't mind if there were a few people around, but ultimately wanted it to be less public and more intimate.

Step 1: What are your priorities?

Some proposers want a specific location, scenery, time of day, crowd, or attendees. Make sure you bring this up to your photographer (if you're planning to have your proposal captured). Your photographer will make recommendations about the best spot for the best lighting.

Shiv and I had multiple planning phone calls and email chains discussing the best spots, back up spots, and what to do if it rained. We worked through the possibility of people accidentally wandering into the frame, and what he vs. what I was responsible for as the photographer. We settled on 2 spots - 1 being the primary at the south side of the Boston Public Garden's lagoon, and the second being slightly further up, in case of rain, mud, etc.

Step 2: Lighting & Direction (for the best photos)

Once Shiv chose the spot, I recommended the right direction to face. The way we discussed positioning:

Shiv would identify me at the park when walking to the spot. He would make sure he'd angle his body so that taking a knee would point his left butt cheek towards me, giving me an angle of his face, the ring, and her face fully in view. I chose where to stand based on the position of the sun to prevent shadows or any flare.

Step 3: Fine-tuning the details

Once we figured out where and how, we talked through the logistics and little details. For instance, how would Shiv make sure he and Juhie didn't have masks on for the surprise proposal? I recommended asking her to take a selfie together once at the agreed upon spot. What about making sure Juhie was facing the right direction? I recommended Shiv take her hands and physically turn her, getting on one knee in the process. This would make sure she was facing me, and also that her mask remained off. Note: we were 100% more than 10 ft away from any other BPG patrons, and were very careful to stay safe.

In the planning process, Shiv also shared his intended walking path by creating a quick "treasure map" of where he and Juhie would be entering the park and the path they'd take to get to the proposal location. This allowed me to be covertly on the lookout for them, and to also blend into the background.

Alternative to surprise proposals:

Although most proposers plan to pop the question as an event on it's own, there is another very popular way to propose and get fantastic photos of the surprise: photo session proposals. This is incredibly useful when the person being proposed to: would know something was up, or would want to be dressed up for the event, and would not appreciate the proposal completely out of the blue.

Telling your partner you booked a couple's photography session would allow both of you to prepare yourself (hair, makeup, outfits) and would explain the photographer. During the session, you could use a prompt/plan with the photographer to have the proposee get into position without even knowing it!


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