A surprise proposal in Regent’s Park Japanese Garden

Dillon (he/him) always knew he was going to propose to Trey (he/him) in London. They are both New York based, but absolutely adore the city and always stay at The Landmark just round the corner from Regent’s Park. Dillon contacted me through the fabulous Rebel Love Directory and we set the plan into action. He was going to fly Trey over here on the premise of a brand trip and tell him they were going on a cruise that left from Southhampton that night. The reality was VERY different…

Location: Regent’s Park, Mission: Capture the proposal undercover

Proposal photography is a whole different ball game than weddings. I’ve usually only spoken to or met the person proposing, and often it requires pinpointing an exact location without having visited that location together. Here’s my full proof method for nailing it every time:

It’s all in the planning

I make sure we’ve had a good zoom chat to nail down a timeline and every moment in between so that the only surprises here were for Trey! We had added element of Dillon also flying out five of their family members who were hiding in the Artesian bar in the Landmark Hotel so they could all spend a few days in London celebrating the newly engaged bubble. After our call we worked out the fool-proof timeline and I sent an incredibly accurate stick-person drawing of the spot so that we both knew the right spot for the big moment:

Adding Content Creation

Dillon opted to add my team member Amy (also my sis-in-law!) to the proposal package to film all the incredible moments on iPhone too. Amy was also able to assist with location watch. We arrived an hour early to the spot to claim our territory on top of the waterfall in Regent’s Park and Dillon dropped us a location pin on WhatsApp so that we were able to track their movements and know when to be ready to rock. The spot is right next to Regent’s Park Open Air Theatre so we got to enjoy the entirely of Cat’s while we waited.Sadly it was over before T&D arrived - I was buzzed at the idea of ‘Memory’ being their proposal soundtrack!

LGBTQIA+ Regent's Park Proposal

Photos in Regent’s Park Japanese Garden

Japan is Trey & Dillon’s other favourite place, so it made total sense to get engaged in the hidden Japanese garden of Regent’s Park. Once we had revealed ourselves from our hiding spot atop the waterfall, Amy and I joined them on the bridge and spent 45 minutes popping them in some beautiful spots around the gardens and letting them sink into that gorgeous bubble that is being newly engaged! Dillon had SO many stories to share with Trey, including revealing surprise number two; they weren’t heading on a brand trip that night, they were actually spending a few days in London before flying to the Mykonos! We stopped for a final moment in front of the glorious gate that marks the entrance to the Rose Garden when T&D froze. The date above them said ‘6th May’ - their anniversary date and the date they are planning on getting married in 2028! It turns out that 6th May 1935 was the date Regent’s Park Rose Garden was opened to the public. We love a universal alignment moment.

A final surprise in the Landmark Hotel

Amy and I said our fake goodbyes and scurried off to the Landmark Hotel to hide in the Artesian bar with Dillon’s mum and sister and Trey’s parent’s and Aunt (with his sister on FaceTime and present as a cardboard cutout!) As D&T entered the bar to ‘Congratulations!’ the tears came all over again. After hugs and a couple of photos of the group Amy and I left them for real this time to sit down with a cocktail and enjoy their evening in London.

It’s such a privilege to be able to document proposals - especially ones that have had the huge amount of thought, planning and attention to detail as this. I bow down to Dillon’s vision and am so happy I was able to help him execute a little park of it. If you are planning a proposal and would love it documented like this, we have a special package just for you!