Three Strikes, Three Locations: The Secret to Successfully Saving an Engagement

From Castle Hill Chaos to Bailey Beach: How a 15-Minute Pivot Secured the Perfect “Yes”

Given that 85% of my clients are out-of-state and unfamiliar with the proposal location, meticulous planning is essential to ensure a successful surprise proposal photoshoot. Ahead of the proposal, I have a Zoom meeting with my client, during which the plan is developed with the primary goal of saving an engagement from logistical failure.

Matt, unlike many of my clients, had a sentimental location in mind – Bailey Beach at the end of Newport’s Cliff Walk. I expressed my reservations about this choice due to the restricted parking, as it could impede my ability to photograph the proposal. Parking must be 100% guaranteed, as a lack of access is often the first hurdle when saving an engagement.

We explored other options, and Matt ultimately chose the iconic Castle Hill Lighthouse. While it’s a stunning location, and I’ve captured numerous proposals there, it comes with inherent challenges. Firstly, the lighthouse’s popularity means a constant flow of visitors could disrupt the proposal moment, necessitating waiting for a less crowded time. Secondly, the Castle Hill Inn is a wedding venue, and wedding parties often use the lighthouse for photos, temporarily restricting access—a constant threat to saving an engagement at this spot.

I typically use two spots at the lighthouse: the deck and a more secluded area. Matt expressed interest in both but decided to confirm with the Inn beforehand. Fortunately, no wedding was scheduled on the day of the shoot, so we opted for the lighthouse deck. With the proposal set for 3 PM on November 9th, I kept Matt updated with text messages: one when I left home and another 30 minutes before the scheduled time. As I arrived at the lighthouse, my heart sank. There were chairs set up, indicating that a wedding had just finished or was about to begin, with sunset only two hours away—immediately putting me in crisis mode for saving an engagement.

Oops, there’s a Wedding

A scenic outdoor setting at Bailey Beach with chairs arranged for a surprise proposal.

Immediately texted Matt to inform him of the situation and suggested moving the proposal to Castle Hill’s lawn, a less preferred option but the only viable one at that moment for saving an engagement. After sending the text, I approached the Inn to inquire about the wedding’s timeline. A valet, unable to provide specific information, directed me to the front desk. There, I learned that the wedding was still to take place, confirming that the lighthouse was out of the question. I thanked the front desk and headed to the lawn, determined to continue the process of saving an engagement. I captured a photo of the new location, annotated it, and sent it to Matt, finalizing Plan C in this unexpected crisis.

Suggested Spot on the Lawn

Romantic proposal at Bailey Beach overlooking the ocean, capturing a special moment for Matt and Maryanne.

Here is the rewritten text, incorporating the keyword phrase “saving an engagement”:

For the moment, the day felt momentarily secure, but the task of saving an engagement was far from over. My phone rang. It was Matt, expressing discomfort with the lawn and requesting a return to Bailey Beach, our original, discounted location. I agreed but quickly realized the logistical challenges. “Sure,” I said, “I’m three minutes from my truck and a ten-minute drive from the beach, but I have no idea where to park.” Matt suggested Rovensky Avenue.

I’d never felt so unprepared during the process of saving an engagement. I’m typically meticulous in my planning, including the precise positioning of the sun. A sense of unease washed over me as I rushed to my truck, but I knew I had to roll with it. I navigated Ocean Drive, following the tourists’ slow pace as they drove admiring the scenic beauty. Meanwhile, I struggled with the GPS, trying to locate Rovensky Avenue, all while contemplating the best beach access point and potential proposal location—every second was crucial for saving an engagement. But first things first, I needed to reach the beach.

I found Rovensky Avenue, a small park with limited street parking, heavily restricted during the peak season of May to October. Fortunately, it was November. Earlier in the day, Matt had shared his GPS location, and as I parked, I confirmed they were nearby, giving me a crucial edge in saving an engagement at this final spot.

I know where you are!

A romantic moment captured during Matt’s surprise proposal to Maryanne at Bailey Beach, featuring ocean scenery and a scenic backdrop.

I walked the four blocks to the beach, consulting Google Maps’ satellite view to identify a potential beach access point at the end of the Cliff Walk. As I approached the deserted beach, I needed to devise a plan. A rocky outcrop near the beach club seemed like a suitable hiding spot for my cameras. I captured a photo of the designated proposal spot and sent it to Matt, informing him of my red jacket and my intention to walk along the beach toward them, transitioning to the rocks and my cameras as they approached.

X marks the spot

A beautiful day at Bailey Beach capturing a surprise proposal with scenic ocean views and sandy shores.

The moment arrived. Matt dropped to one knee, and with tears in her eyes, Maryanne said, ‘Yes.’ A few minutes later, their families emerged with a bottle of champagne to celebrate the happy couple.