September 23, 2020

Anna & Justin | Okaloosa Island, Florida Proposal Photographer

Iā€™m Stephanie, a wedding + lifestyle photographer based in Destin, Florida and Warrenton, Virginia. Whether Iā€™m by the mountains in Virginia or the ocean on the Florida Gulf Coast, my soul feels at home, surrounded by rural living and the raw beauty of nature. I genuinely love what I do, and feel so passionate to share the enthusiasm and joy of these celebrations with you!

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Anna & Justin | Okaloosa Island, Florida Proposal Photographer

This post is EXTRA special. One because a SUPER sweet proposal happened recently!!! Two (spoiler alert), Anna said YES!!!! Three, this is the exact place where Alex proposed to me too. šŸ™‚ When Justin reached out to me about a proposal on Okaloosa Island in Florida, I couldn’t say “YES” fast enough!! There’s something about proposals that get my heart racing … Although, I’m sure not quite as fast as Justin asking the question. šŸ˜‰ But it’s such an exciting, quick moment that occurs, and I want to make sure the plan executes as smoothly as possible. šŸ™‚ I could tell through our email exchanges that Justin also wanted to make sure everything was perfect as well. So “Operation Sunset Proposal” was set and ready to go!

Anna & Justin | Okaloosa Island, Florida Proposal Photographer

We cautiously watched the weather alllllll day Thursday hoping to have a beautiful sunset. After some potential evening storms were threatening that chance, we decided to postpone to the following day ā€¦ I don’t know HOW in the world Justin held himself together for another evening!!! HAHA! Somehow, he managed. šŸ™‚ Anna was curious why he was so bummed about the weather, but she continued enjoying their vacation time. Friday came, and the weather was perfect for “Operation Sunset Proposal!!!” And I could hardly wait to meet them! As soon as they walked up, Anna looked like a super sweet southern bell! And goodness, they were both not only as sweet as can be but also one GOOD looking couple! Don’t you agree?! šŸ™‚ Check out their proposal story below and be prepared to have your heart MELTED!!!!

The session started like any typical session…

As we got started, I couldn’t tell if Justin was nervous, but I was nervous for him!! HAHA! I knew that it was going to play out perfectly no matter what happened, though. šŸ™‚ So we found a little private spot on the beach and photographed with Justin’s bag hiding the ring within reach. Justin and I ran through the playbook through our emails, so he knew when it was GAME TIME! But we wanted to trick Anna and play the first part of the session like a typical session ā€¦ And it worked. šŸ˜‰ HEHE!

And then we tricked her!!!

I asked Anna to step five steps in front of Justin and NOT to peek because he would sneak up and attack her with a BIG bear hug! šŸ™‚ During her anticipation, Justin cautiously dashed to the bag behind her and pulled out the ring. He got down on one knee and waited for her. After Anna waited for him to attack her for a SOLID minute, she started to wonder what was taking him so long … So she caved in and peeked over her shoulder. As soon as she saw him on one knee, she threw her head down in disbelief, ran to him, and crashed down to her knees with tears in her eyes. **GUYS. I have chills and eyes filling up with tears all over again writing this because it was the SWEETEST reaction!!!** See how everything played out below!!! All THREE of us were in tears!!! I think she was a little excited. šŸ˜‰

CELEBRATION TIME!!!

We spent the remainder of the proposal on Okaloosa Island, Florida, playing in the glowy light! It was the perfect magical evening that we all hoped to have. <3 Even if Anna didn’t realize what Justin had up his sleeve. šŸ˜‰ They ended the evening by celebrating at McGuire’s Irish Pub (so fun) and calling family/friends. The perfect ending to an unforgettable vacation!!! šŸ™‚

CONGRATS, JUSTIN & ANNA!!!!

Thank You!!!

Thank you, Justin, for entrusting me with photographing this VERY special occasion!!! WOW! I’m still in awe … You two are as sweet as can be, and I know your family and friends have to be THRILLED for you!!! I wish you both the very best and hope to see you guys again in the future!!! šŸ™‚ CONGRATS!!!!


Stephanie Messick Photography, LLC is a Navarre, 30A, Destin, Okaloosa Island, and Florida Panhandle Beach Proposal, Lifestyle, Wedding Photographer, also serving Northern + Central Virginia. Learn more HERE or contact her HERE and ask about the Destin, Florida Portrait Photographer Special!

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