Jessica and Avery

Orange Beach, Florida



Photographer | Justine & Wayne | @justine_cunningham

Jewelry | Kendra Scott | @kendrascott

From the Photographer

Jessica and Avery were traveling to Orange Beach with family and wanted a destination engagement session. Their proposal is amazing. He proposed in a helicopter with Marry Me? spelled out with people on the ground.

Let’s start at the beginning. How did you two first meet?

We both went to Crossville High School. He graduated in 2013 and I graduated in 2014. So technically we have known each other our whole lives. I always had a crush on him, but never actually let it be known. He on the other hand would always come sit on my desk and aggravate/flirt with me, but nothing ever actually came of it. In 2013 (his senior prom, my junior prom) we were awarded “Best Dressed” together and I guess you could say that’s where things started! A few months passed and we ended up going to a rodeo with a mutual friend and haven’t stopped seeing each other since!


What makes your relationship special? Tell us some things that you both value in your time together. What makes your relationship unique?

We both share a huge passion for animals! Most of our quality time is spent working around the farm. He completely understands my love for everything with fur and embraces it to the fullest. If I ever get a crazy idea to get a new animal, whether it be a Dog, Goat, or Hedgehog, if I don’t bring one home first, he will! Lol


How did you know your partner was the one? When did you first know this in your relationship?

I don’t know that there was ever just a “This is it” moment. To know Avery is to love Avery. He has the best personality, and he’s one of the most thoughtful, & loving people I’ve ever met. As time went by we grew closer and our love got stronger. He became my best friend and I became his. Avery’s dad did say “He knew something had to be different about me because no girl had ever came first to Avery working on the farm, but when he started dropping things that needed to be done to come see me and take me out, he knew!”


Give us all the details about the proposal. How and where did it happen? Was it a surprise? What was the planning process?

So a little back story… We had been working on remodeling our house day in and day out for weeks and were both stressed to the max! So at the beginning of the week Avery said “I promise Saturday we will go out to eat and celebrate since next week is our 5 year anniversary.” Friday night rolled around and Avery was super late coming in from work, but I didn’t think much about it! Little did I know he was at a local field writing out “Marry Me?” with paint that they use to paint baseball fields with!! Saturday morning I woke up and could not wait to get off work and go on our date. Of course I wore my new outfit and got all dolled up, only for me to get to his house and him say “I think we’re just gonna got out with my parents tonight.” WHAT!? I’ve waited all week for this day and now we aren’t going!? I was mad, obviously. Little did I know, we couldn’t go on our “date” because it was raining! Fast forward to Sunday morning, Avery texted me and told me to get ready and come to his house. So of course I did just that (still pretty upset I didn’t get my date night). Once I got there, we got in the truck and headed to go get something to eat. At this point, Avery would not dare tell me where we were going to eat at. I thought he was just trying to do something special to make up for the night before! As we headed down the road, Avery handed me a blanket and made me cover my eyes with it. We drive for what felt like an hour. We finally reached our destination and the anticipation was killing me, but he still wouldn’t let me see where we were. Avery guided me into a building then took the blanket off my head and I was in a little local airport. We then shook hands with the pilot and rushed to get on the cutest little private airplane! I thought to myself “this is it!!” Once we got in Avery handed me a tiny little black box (what I thought was a ring) and said “Happy 5 Year Anniversary.” It was a pair of diamond earrings. It completely caught me off guard because I knew there was no way he was going to give me earrings and a ring. We flew over the lake for awhile and Avery suggested I tell my parents I’m in a plane! So I was texting all my family and friends showing them what a sweet date I was on. Then the pilot said, “I’m not really familiar with this area, what are we flying over?” So I looked out the window and then I saw it. In HUGE letters written in a field below, Marry Me? I turned and looked and seen my sweet boyfriend holding the most perfect ring I could have ever dreamed of!! And to top it all off, the question mark in the field was made of all our friends and family down there waving at us!! It was the most magical day I could have ever asked for!!


We’re all about the bling… Tell us all about that ring!

My ring is 1.25 karats! The setting is Rose Gold! The center diamond is Emerald cut and it is surrounded by a halo of smaller diamonds!


Are you excited to start planning your wedding day? Do you have any ideas in mind yet?

Planning the wedding is an adventure in itself, but has been nothing short of a dream come true! We are getting married October 5, 2019 at Dry Creek Chapel in Leesburg! We absolutely can not wait.