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How to Plan a Surprise Proposal | Pittsburgh Photographer

I never in a million years thought I would be on the front lines of a surprise proposal. You see it in the movies, you read about it in all the gushy romance books but having the chance to photograph a surprise proposal gave me all the feels. Working with RJ and planning out the logistics was so much fun and a pleasant break from my regular work with families and branding.

Two weeks before the surprise RJ and I hopped on the phone to talk logistics. There'd be nothing worse than planning this beautiful surprise only to find out you and the photographer weren't on the same page. I have put together 5-tips for planning a surprise proposal with a photographer.

Jules & RJ arriving onsite for the surprise!
Jules & RJ arriving onsite for the surprise proposal!

Tip #1 Meet with the photographer to discuss details.

Planning a surprise proposal takes more planning than a general session. Your photographer is going to be a great resource to use when planning out how the surprise proposal will go. The photographer will help you brainstorm possible ways to plan the surprise as well as what to do when something goes wrong. I recommend meeting your photographer in person or speaking over the phone.

When you talk with your photographer, have as many details as possible and have your questions ready. You can my guide How to Plan Your Surprise Proposal to help you ask the right questions.

Surprise proposal in Pittsburgh, Pa with woman and man laughing.
Surprise proposal in Pittsburgh, Pa.

Wait, that's not a ring.
Wait, that's not a ring. RJ tricked Jules with a fake out proposal before he popped the real ring.

Tip #2 Build in buffer time.

Buffer time is KEY! What do I mean by buffer time? When you are planning a surprise proposal planning for the unexpected is key! My suggestion is to add on at least 30 minutes to your timeline or to create a window of time that something will happen.


Dinner is 5-6:30 Proposal will be at 7 in Mt. Washington

Plan to arrive between 7-7:30, schedule the photographer to arrive 15- minutes prior and leave a large enough window of time in the event you encounter slow service, traffic, trouble parking.

Another thing to consider is building into the contract a payment schedule in the event you need the photographer to stay work longer. You can both negotiate the added cost for each added 15 minutes.

Surprise proposal in Lawrenceville, Pittsburgh.

Jules reaction to a fake ring.
Jules reaction to a fake ring.

Tip #3 Prepare for the unexpected.

Plan for the unexpected. During your consultation with your photographer, be ready to have a backup plan. What will you do if it rains, someone gets sick, the location you picked has too many people.

Your photographer should have suggestions, and you most certainly want to make sure you have a thought-out a backup plan.

Surprise proposal, couple looking down at ring in Pittsburgh Pa by LeeAnn K Photography.

Engagement ring close up by LeeAnn K Photography

Couple kissing by LeeAnn K Photography in Pittsburgh PA

Tip #4 Take it slow.

During the proposal itself TAKE YOUR TIME. Soak at the moment and make it last. Doing this will not only help you calm your nerves, but it will also give the photographer the time to catch every moment. When you pop that question and go in for the kiss, remember to take it all in. When we feel nervous and excited our natural reaction is to move quickly, but you won't regret slowing down.

Surprise proposal picnic setup in Pittsburgh, PA by LeeAnn Stromyer

Tip #5 Plan ahead of time.

The moment you start to think about your surprise proposal is the moment you should reach out to potential photographers. Many professional photographers book out 3-4wks in advance. Reaching out early to photographers will give you enough time to pick the one you love verse the one you like.

Couple taking a shot after surprise proposal! Photo by LeeAnn Stromyer in Pittsburgh Pa

Popping champagne for a celebration!

Champagne bottle popped, couple celebrating engagement!

Engagement photo by LeeAnn Stromyer in Pittsburgh Pa

Engagement photo by LeeAnn Stromyer in Lawrenceville, Pittsburgh

Engagement photo by LeeAnn K Photography in Pittsburgh Pa

Are you ready to book a photographer for your surprise proposal?

Click the button below to fill out my contact form. Surprise proposals start at $499 this includes your proposal planning session, 60 minutes of shoot time, and a set of 30 edited images. Packages go up from there and can include more shoot time, extra help in planning the proposal, and prints from your session!


Hey friend!


I'm LeeAnn a Pittsburgh-based personal brand photographer helping womxn and queer-owned businesses create memorable brands with unique captivating photography.  

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