When Treg Dore contacted me about photographing his surprise proposal to his now fiancé, Bailey, we were challenged with finding a way to photograph it without blowing the surprise. He and I cooked up a plan to ensure that not only would he have beautiful photos of his proposal, but Bailey would also have absolutely no idea what was happening, and of course, she would say yes.
Treg decided that he wanted to propose to Bailey on the lake at Rip Van Winkle Gardens following a tour of the grounds. He’d already gotten permission from Bailey's family and used her grandmother's diamond as one of the stones in her engagement ring. He planned to lead Bailey to end the tour near the beautiful ruins on the lake where Treg would get down on one knee. We decided on Golden hour with the sun setting at their backs, but we still had to figure out how to explain my presence without giving it away.
I hatched a plan. I instructed Treg to show up at the spot, to pretend he doesn’t know me and I would take care of the rest, which took a great deal of trust on Treg’s part.
Bailey and Treg arrived at the spot to overhear my phone conversation with my husband, stressed and complaining about how something had gone majorly wrong. I tell my husband “I will try to figure something out and I will call when I'm on my way home.”
Bailey begins to turn the corner with Treg and walk just past me when I stop her with an abrupt; “Excuse me.”
The stop.
“Hi, I know this is strange but I have a little situation, would you two happen to be a couple?” I ask nervously trying to hide the fact that I obviously know the answer to that question.
Bailey responded - “Yes.”
I introduce myself as an up-and-coming photographer and explain that I’d planned on taking photos of a model couple for my portfolio, and the models canceled on me very last minute after I’d already paid for sitters, and the fees to be able to photograph the session.
“I’d hate to leave empty-handed. Could I beg you to take even a few photos for me in front of the lake?”
Again, Bailey responds, “Yes.”
She didn’t realize her next, “yes,” was going to be the most important yes of all!
So, I walk the couple over to the spot Treg selected while making small talk; asking their names and things. I even mispronounced Treg’s name on purpose, called him Trey to add an extra layer to our elaborate ruse. I pose them and take a couple of photos. Ask their names again pretending to have trouble remembering, acting nervous about being so “new” at this!
We take a few more shots and then I decide to do one with them holding hands back to back. I position Bailey first and Treg drops down on one knee. Before I could even tell her to turn around, she notices his shadow on the ground behind her and she turns stunned.
He asked.
She said “Yes!”
She saw her ring with her grandmother's diamond and cried.
Her first comment to me when she realized our entire interaction up until that point was a complete lie; “Are you an actress?” Beaming with pride, I tell her I really am a photographer, though not a beginner, and explain that Treg hired me to help him capture the proposal.
Here are a few more favorites from their session!
