anthony's surprise proposal at the weekapaug inn

When Anthony contacted me to discuss his surprise proposal to Kerri, my interest was piqued slightly more than usual. Why? The location for his proposal was the Weekapaug Inn in Westerly, Rhode Island, somewhere that I have never had the opportunity to visit. The Weekapaug Inn’s sister property is The Ocean House Hotel, a historic beachfront hotel where I enjoy any opportunity to work or dine. Earlier in the year, Brian Honan, the Ocean House/Weekapaug Inn’s new Director of Sales/Marketing, visited my studio for a headshot. Brian spoke very favorably about the Weekapaug Inn planting a solid seed of interest; now I have a reason to visit; excellent, but I digress!

I will only undertake a surprise proposal photoshoot after first understanding the lie of the land. Each shoot requires a detailed plan (and a plan B and sometimes a plan C), and I could not offer Anthony a clear plan because I had never been to the hotel. I needed to visit the property; this was an excellent opportunity to take my wife for dinner; I could kill two birds with one stone. However, the following week, Anthony called and offered to meet me at the Weekapaug Inn to walk the hotel’s property to develop a plan; perfect! Sorry Mags, we will have dinner later in the year.

On a grey, drizzly night, I met Anthony at the Inn, and we walked around looking for an ideal place for his proposal. We found it, a secluded spot with two Adirondack chairs overlooking the water. However, alarm bells were ringing in my head “where could I hide?” “could I hide in plain sight” and “at best, this was going to be awkward.” I pointed out to Anthony that this would not work if other guests sat in the Adirondack chairs. Anthony had considered this and raised this point with the hotel staff, and they offered to put a ‘Private Party’ sign at the entrance to the path to ‘the spot’ to play defense.

Private party

As I was noodling this situation, Anthony said, “what if you pretend to be a nature photographer? And when we arrive, we say hello to each other, and then I will ask you to take a photo of us with my phone. After you return my phone, I will drop to one knee.” This ruse would work!

I took a demo shot of the location with the hotel building in the background; it would make a nice scene.

On the day of the proposal, Anthony shared his location with me via GPS, and I with him. Location sharing is my favorite way of keeping an eye on my clients because I can track them as they move toward me. If only James Bond had this technology!


I sent Anthony a text when I left my studio and another when I arrived.

As I walked to the proposal spot, a member of the Weekapaug’s Inn staff enquired – very politely – about my photography; I explained that I was there to photograph a couple of their guests. As we continued our conversation, I mentioned that I had photographed Brian earlier in the year, and he said that Brian was on the property; I passed on my regards, and on I went.

When I got to the entrance to the path to the proposal spot, there was, as promised, a ‘Private Party’ sign. I followed the path to the Adirondack chairs and had the place to myself; the sign did the trick.

I opened my backpack and laid out two cameras to make it look like I was a nature photographer. When I turned around and looked at the proposal spot, there was one major problem; I would be looking directly into the sun. It was cloudy when we visited, and we did not know the sun’s exact position, but now it was a problem. I figured out a workable angle, took a photo with my phone, and I sent a text to Anthony asking him to keep Kerri on his left, and I would make the light work.

I checked the GPS and Anthony’s location; I had about 30 minutes. I could only sell the fact that I was a nature photographer if I looked like a nature photographer, so I set up my EOS 1D Mk IV with a 70mm – 200mm f/2.8 lens – a big lens – that would do the trick! I put the camera I would use for the proposal shoot around my neck, my EOS 1DX with a 24mm to 70mm f/2.8 lens.

I sat on a rock, 10′ in front of the pair of Adirondack chairs, and pretended to take photos of the bird life; I checked my GPS location tracker and saw that my couple was on the property. I could not look around; I could only look through my lens because I did not know when they would arrive. I took photographs of a variety of seabirds. As I was framing up another shot, I heard voices.

nature photographer

I could now feel their presence as I looked through my viewfinder.

Anthony said, “Hello;” I turned around and offered my greetings, and he asked what I was photographing. I pointed to the spit of land in front of me and explained that it was a hot spot for birding. We chatted for a couple of minutes, and then Anthony, as planned, asked me to take a photo of them using his phone.

I stood up with the EOS 1D MK IV around my neck – I had taken a test shot 10 minutes before they arrived – and walked towards them. I took the phone and took a couple of pictures, and just as planned, I returned the phone, and Anthony dropped to his knee.

“I love it when a plan comes together” ~ Colonel John “Hannibal” Smith (The ‘A’ Team)

If you would like to learn more about surprise proposal photoshoots, pop-over to the Proposal/Engagement web page for details on pricing and lots of information for planning the perfect surprise proposal.


After photographing many, many, surprise proposals…

Never do anything different. A behaviour change will give the game away!