Jennifer said yes! Surprise Proposal Session at Old San Juan, Puerto Rico

About a year ago, I stumbled upon Garrett's e-mail inquiry on Puerto Rico proposal ideas and packages on my inbox:

Hi Camille! I'm reaching out to you about potentially booking you for a surprise proposal session the evening of December 22nd. I'm not entirely sure of the spot in which I plan to propose to my girlfriend, but we're going to be staying at a Condado hotel that night and I wanted to get the ball rolling on finding a photographer for the surprise. I've been looking at your website and your work looks incredible! As I continue to plan out the proposal I can maybe brainstorm with you to see what you think as far as location/timing goes? Looking forward to hearing from you!

I love proposals, and until 2019 I didn't shoot enough of them, so I was really excited. I immediately sent him a link to my photography packages and a link to my blog post on Puerto Rico marriage proposal ideas.

After a few weeks, Garrett was ready to commit! After touring the whole town on google earth, he found Castillo San Felipe del Morro as the unique place to propose to Jennifer. We went on a booking consultation over the phone. I talked to him about my thoughts and tips on making this proposal happen effortlessly without Jennifer knowing!

The Proposal Day

On the proposal day, I arrived an hour and a half before sunset to El Morro. Once I perfected my camera settings, I did what's most difficult for me during these sessions: I waited. Eventually, I saw a cute couple walking toward my direction; they were here!

There are three different persons in a proposal: the suitor, the proposee, and me, the sidekick/photographer. Most times, the proposee isn't aware of the photographer's presence. This means I have to be extra careful so I don't spoil the surprise. If we're on a landmark, I'll pretend I'm a tourist, and I'll intentionally ignore the couple until I notice some movement.

How do I plan this without spoiling the surprise?

This is a question I get asked a lot! And something I always do after the successful proposal is to ask if there were any suspicions. Although some say they were 100% surprised, many proposees will become suspicious or "accurately wishful" over stuff we have no control of. There are some things that you can avoid a suitor:

  • Be suddenly particular about clothing and looks over a specific day. If you're the kind of person who never takes hair, makeup, and nails into consideration, this might make your plans obvious. Employ some of your partner's best friends to help inconspicuously plan these for you.
  • Fail to make a thorough plan. If you make a big deal about being all dressed up for a random sunset beach walk, well, a proposal might be expected. I always suggest my clients make a fancy dinner reservation later in the afternoon that gives enough excuse to dress up. The walk won't feel as intentional.
  • Make too much eye contact with the photographer. I know it's the anxiety talking.
  • Give your backs to the camera, and then I have to make a run for it, risking to bring too much attention to myself.
  • Worry too much. Keeping this a total surprise is not the end-all, be-all. Be in the moment, and remember that the proposal will be beautiful and memorable no matter what.

I always position myself facing the location I want the suitor to place themselves at. This is regularly the angle where I believe there are the best scene and lighting conditions. On Jennifer and Garrett's, tourists moved into our view at the last minute, so Garrett kept his cool and walked further away. I followed his lead and eventually captured his proposal when he felt ready. Jennifer said yes, and they held into a beautiful embrace that had everyone swooning over them.

After the initial shock passed, I greeted the lovely couple, and we went on for a walk around the grounds of El Morro for a short engagement session before sunset.

Garrett, thanks for sharing this day with me and trusting me with its memories. I hope every day of your life together is as lovely as your engagement day.


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