Surprise Autumn Proposal

David & Maddy – October 11, 2020

Proposals are such raw, meaningful moments that getting the privilege of photographing them is one of my very favourite opportunities. They are so precious no matter what, but they REALLY hit hard when the people getting engaged are close to your heart! In this case, this beautiful couple are none other than my husband Andrew’s younger brother David and his new fiancée, Maddy! It was so surreal to fly across a field snapping photographs as David got down on one knee, knowing that this sweet girl in raptures was now going to become my new sister!!

David’s proposal was even more gripping than normal because David and I didn’t get to do an in-depth walk-through at the location in advance like I usually do with proposals! I was gone all weekend being the second photographer for a wedding, so for a decent amount of the weekend we were excitedly texting back and forth with plans and sending photos to give context and Google map coordinates! It was so much fun and made for a wild experience with secret phone calls and messages all weekend behind Maddy’s back!

David put so much thought and care into his proposal and throughout it all it was so clear how much he values Maddy and wanted to make it perfect for her! The date of the proposal was very meaningful to them, as it landed exactly on their 1-year anniversary, and the location was special as well; this was their secret spot to come and dance together whenever the mood struck them!

Maddy didn’t know how to dance before she met David, so to give her some privacy to learn, David found this little road off the beaten path to take her to dance surrounded by farmer’s fields!

This dancing date started out just like the others, with David parking his car to the side and setting up his speaker to give them music. They started dancing and I got into position to snap a few quick shots without giving away my hiding place, which was a fair distance away from the proposal spot.

I waited silently, obscured behind hay and tall grass, for the moment when David would drop down to one knee.

And then it happened!

As soon as I knew that Maddy was completely focused on David and wouldn’t even notice me, I jumped up and ran to get closer, higher-quality images of this moment! Maddy was moved to tears and David looked like the happiest man alive, so I knew without a doubt that she had said, “Yes!”

After a few minutes, I ran up to them and we laughed and cried together as the surrealness of it all made us all a little crazy with joy! We were walking on sunshine and loving every second of it!!

Once we had a chance to regain our composure, we took a few minutes to document their very first pictures as an engaged couple! We are going to have a full-length engagement session once the winter hits, but in the meantime we couldn’t resist celebrating their new relationship status with a short but sweet photo session!!

David & Maddy, Andrew and I love you guys so much and are so excited for you to take this next step in your relationship!! We know there are great things in store for you and we are so excited to see how God continues to bless you as a couple. I can’t wait to capture your official engagement session this winter!!

Enjoy a few of my favourites from your proposal!

  1. Victoria Sawka says:

    Congratulations. Love these pictures.

  2. Helen Belanger says:

    Congratulations David and Maddy the last one to leave the nest! Jillian thanks for sharing beautiful pictures

  3. Susan Hodges Marlowe says:

    Such a perfect proposal but that doesn’t surprise me with David! Congratulations and many many blessings over you both. Beautiful photos from an amazing photographer. Just perfect!

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