Surprise Restaurant Proposal/Engagement Photoshoot - West Village, Manhattan (NYC)

Ah, my first surprise proposal shoot, and an eventful one at that: my equipment was stolen from me during this session! But more on that later.
Proposal shoots require a good deal of planning and coordination between the photographer and the proposer, especially if it’s a surprise! The big question was set to be ‘popped’ over dessert at the beautiful One If By Land, Two If By Sea restaurant in the West Village. The groom-to-be had notified the restaurant that he would be proposing, and got permission from them to have a photographer capture the event. I then had to coordinate with the restaurant regarding what kind of equipment they would let me bring, where the couple would be sitting, and where I would be able to set up where I would not be giving myself away to the bride-to-be, the other diners, and the staff. It was a VERY dark restaurant and they forbade the use of a flash, so I had to rent a lens with a much larger aperture in order to be able to capture the shots in what was almost and total lack of light. After much finagling, I was finally able to secure my position, and patiently wait for the big moment. The groom and I kept in touch during the dinner via text to make sure we were both on the same page with regards to the timing, since proposals are often quite short you need to be able to get as many photos as possible as quickly as you can right when the moment happens.
The proposal went off without a hitch, she said yes, the restaurant cheered, and we got our shots.
After dinner, we went outside to take some engagement/couples style shots to add to their special evening.
One of the shots required us to be running in and out of the street to avoid traffic as a few of images were of them standing in the middle of the road. This being the case, I had to leave some of my equipment nearby on the sidewalk as I couldn’t carry it all on me due to how quickly we needed to be in constant motion. During one of our middle-of-the-road sets, a random passerby STOLE my equipment that I had on the sidewalk. And although I wouldn’t notice for a couple of minutes, I didn’t even realize they were gone until the perpetrator RETURNED them back to me and apologized for having nicked them! Needless to say, all 4 of us were really taken by surprise by this whole turn of events, and while the evening could have ended very badly for me, it ended up being very strange and serendipitous, especially for New York City!
The couple and I had such a great time, really bonded over our session, and they loved their final photos so much that they later asked me to shoot their wedding!

Here are a few of my favorite shots from this very special evening:

To see more examples of this style of photography, take a look at my couples and engagement portfolio >>

All images in this blog post were shot on a Nikon D750, using an AF-S Nikkor 70-200mm f/2.8 lens (rented from K&M Camera), and individually post-processed in Adobe Lightroom using my own custom presets.


Jinnifer Douglass is a full-time freelance photographer based in NYC, shooting both digital and film for individuals and brands such as Google, Door Dash, Make Up For Ever, Squarespace, and more! Specializing in portraits, food, and special events, she works to make every piece of your social and website content ‘Insta-worthy’ with high resolution, full-frame DSLR photography and expert Lightroom editing. Interested in chatting? Leave a comment below, or send an email to hello@jinyc-photo.com!