Proposal · Castle Island, South Boston
Castle Island Proposal — Jordan & Rebecca
“No cover story needed. They had two dogs and a place they'd never stopped going back to.”
- Location
- Castle Island, South Boston
- When
- Saturday, 3:30 PM · September
- Type
- Surprise proposal + portrait hour
- With
- Their two dogs
Jordan came to me a week and a half out with the spot already chosen: Castle Island, where he and Rebecca first met. The only thing worrying him was the cover story, because he didn't have one. He didn't need one. They have two dogs, and walking them out to Castle Island on a Saturday afternoon is just a thing they do — which is the best kind of cover there is, because there's nothing to remember and nothing that can slip.
The plan
The only change I asked for was the time. He'd said four o'clock; I moved us to 3:30, partly for a buffer if anything ran late, mostly because Castle Island fills up as the afternoon goes on and quiet is worth more than light here. Jordan did his part properly — a photo of the two of them, a photo of the dogs so I'd know what I was looking for, and a dropped pin for the exact spot he had in mind. He also asked me to bring roses, so I picked up a dozen and kept them zipped in my backpack the whole walk, because a guy standing around a state park holding flowers is not subtle.
The moment
On the day they came in past the beach and walked the loop like any other Saturday, and I stayed back far enough that Rebecca never looked twice at me. When Jordan stopped and got down, I was already shooting, and the roses came out about thirty seconds later.
Portraits after
Then we spent the rest of the hour on portraits — the two of them, the water, and both dogs, which is exactly the reason to add the portrait hour at Castle Island. You're already out there, you're both still shaking, and the dogs are the reason the pictures look like your actual life instead of a photo shoot.
If you're planning a proposal at Castle Island
- Go earlier in the afternoon than you think — the park fills up from mid-afternoon on summer and fall weekends.
- If you've got a reason you'd already be there — dogs, a walk you always take — use it. That's the whole trick.
- Send me a photo of the two of you (and the dogs) and a dropped pin. I'll handle where I stand.
- Everything else — timing, parking, the loop, what the light does — is in the Castle Island proposal guide, and proposal photography starts at $699.
“Working with Moe was a great experience for us.”
— Jordan, Google review
