A Professional Photographer's Guide To Capturing Surprise Proposal Pictures [Boston Proposal Series]

Author Cristina LaPenna
Date Feb 15, 2021

A few weeks ago I wrote a blog post about different ways that you could pull off getting the perfect picture of your surprise proposal, which included everything from asking a random person to making use of a camera in the ring box.

But, to get the highest quality pictures and have the best chance of them coming out exactly how you always imaged them to, a lot more goes into getting the photos behind the scenes than you would think! So, we went more in depth about what it is like to hire a professional photographer – your own personal “wingman” to capture the moment that you will relive for a lifetime.

I sat down with Jason Corey of Jason Corey Photography to get every detail about what working with a professional photographer for your surprise proposal is like, and based on his experience and local Boston knowledge, he offered some useful advice. The only thing trickier than capturing the big moment perfectly is doing it secretly.

  1. Have you ever helped with capturing a surprise proposal before? If so, how many proposals have you helped with?

I’ve captured 4 surprise proposals and have assisted in coordinating two.

Credit: Jason Corey Photography - Surprise Proposal Photos

  1. Do you find that you are being asked to take photos of surprise proposals more often than you usually would in the past?

I do feel the idea of capturing a surprise proposal is on the up-and-coming. Many “future grooms” or “significant others” usually aren’t thinking about the aspect of capturing the proposal and are more focused on the style of ring, what they will say, location, etc. I am not contacted often for a surprise proposal, roughly about two a year. Although every time I am, it’s an exciting adventure!

Credit: Jason Corey Photography - Surprise Proposal Photos

  1. How do you plan with the significant other where you will be to take pictures of the surprise proposal?

    First and foremost, I ask if there’s a location in mind that is significant to their relationship. I believe this should be the most important aspect and should be taken care of right off the bat. Once a location is set in stone, a great deal of research goes into finding what would work to pull off a successful proposal. I like to plan a walking route that the couple will take, just so I’m aware of their location and can position myself accordingly to remain inconspicuous while capturing the “lead-up” to the proposal.

  2. Keep in mind, during the proposal even if one of us is a foot in the wrong position, or angled a different way, the images could be entirely obstructed or at an unflattering angle. If possible, I try and scope out the location with the significant other prior to the proposal. This ensures we’re both entirely on the same page & we’ll know exactly what the finished product will look like. If scoping out the location is not possible, the significant other & I will resort to figuring out the best route for both of us via a map of the location.

  3. Credit: Jason Corey Photography - Surprise Proposal Photos

  4. Do you hide? If so, where do you hide usually and how do you plan out where to hide?

I don’t essentially hide, but remain rather inconspicuous & in the shadows. I’ll shed off some of my gear to look more like a photographer simply photographing birds or even the scenery. I do try to snag a few shots of the couple beforehand, but quickly and not too often to raise suspicion. I try and plan a route for the couple to walk through, say over a certain bridge or walkway, just so I can then be in a perfect spot to capture the “lead-up” to the proposal. Photographers are everywhere, so if the couple does notice me, the LAST thing that the “future bride” or “significant other” will be thinking is “he’s here to capture my proposal!”

Credit: Jason Corey Photography - Surprise Proposal Photos

  1. Do you reveal yourself at the end to take more pictures after the proposal? How do you do this so it doesn’t feel awkward?

What usually will happen after is an impromptu mini-engagement shoot, where I’ll take some posed & candid photos of that couple within the location. It’s important to me that the couple enjoys their surreal moment of getting engaged, so I will wait a few minutes before actually walking up to them to reveal myself and show them the amazing images of course!

Credit: Jason Corey Photography - Surprise Proposal PhotosCredit: Jason Corey Photography - Surprise Proposal Photos

  1. Can you recommend a location, day or time that is better to propose at in terms of capturing the best photos possible?

I always prefer outdoor rather than indoor. A location with not a lot of foot traffic (unless that’s what the significant other would like) and a good amount of space is ideal. For any outdoor photography, mid-day should be avoided. The time I prefer to shoot is late afternoon/early evening, when the sun is nice & low in the sky (golden hour). The sun gives off a nice yellow-orange side light during this time, creating a nice romantic feel to some images. In the summer, around 6-7pm is preferred, when the 5pm rush of foot traffic has subsided.

Credit: Jason Corey Photography - Surprise Proposal Photos

    1. Do you recommend to the significant other to wear a certain color for the pictures?

    As I do with all my engagement shoots, I recommend avoiding bright whites and deep blacks – but this is totally optional. I prefer having my couples wear whatever outfit they like the most!

    Credit: Jason Corey Photography - Surprise Proposal PhotosCredit: Jason Corey Photography - Surprise Proposal Photos

  1. What are some things that you do to make sure that the pictures come out perfectly?

Planning, planning, planning. I can’t stress this enough. Planning where both the significant other & I will be during the proposal & lead-up to the proposal is what will make or break the images. We both must account for weather, light, foot traffic, and normalcy of actually stopping at a certain location to propose. I will try to have the significant other signal me with something normal (taking off sunglasses, dropping a bag) so I know that’s my queue and he/she about to pop the question. The perfect location, light, composition, and emotion will result in a perfect capture of the proposal. This is a one shot gig, so planning is everything.

Credit: Jason Corey Photography - Surprise Proposal Photos

  1. Can you offer any creative ideas for a couple that is looking to do a surprise proposal?

Location is key - Choose a location that has personal significance to the two of you. Maybe a first date spot, or a location you & your significant other frequent. A location with some nice greenery or beautiful architecture is always a plus! There are many different ways to pop the question rather than just getting down on one knee; maybe have somebody hold up a “will you marry me” sign, or hire a band to play…get creative and really WOW your significant other, plus it’ll make the images look that much sweeter. If the significant other would like their proposal FILMED as well, I have a large list of videographers that would love to capture their special moment.

Credit: Jason Corey Photography - Surprise Proposal Photos

  1. Are there any stories or situations you could tell us to avoid in order for the surprise proposal to go smoothly? How did you handle this?

There was one time where the “future groom’s” phone died as soon as they arrived to the location, so I didn’t have much of an idea where they were – And more importantly wasn’t sure why he wasn’t answering my texts! Luckily we already had a route that they’d walk down set in place, and I was able to track down their location & follow them to the proposal spot.

  1. For more information about planning your surprise proposal with Jason Corey, contact Jason via website - www.jasoncoreyphoto.com or email - Jason@jasoncoreyphotography.com All images are the property of Jason Corey Photography


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