I never shot anything like this before Gabriel asked me. He was visiting Collingwood and was going to propose to his girlfriend and wanted the whole thing captured. It started off as a drone shoot - but explained the challenges in regulations with flying a drones - so we eventually landed on an undercover video of the event. It was something I wanted to do for my own proposal to my wife but never made it happen so making it happen this time was extra cool for that reason.
Gabriel and I made arrangements - like how I'd know it was him and his girlfriend at the park despite never seeing/meeting him before. We arranged possible hand gestures and signals to alert me when it was going to happen, and I even had him discreetly record his own audio using a cell phone - since I couldn't exactly mic him up before hand. After the surprise, we turned it into a short engagement photo and video session. A very unique experience for me and hopefully not the last time I get to capture something like this.