Hailey and Caleb

Wedding Proposal Ideas in Carter's Mountain Orchard

How We Met

Caleb and I met in a very odd way. I had followed him on social media for years without ever really knowing who he was but I had mutual friends who did. At the time, I was having fun in high school and partying with friends every chance I got and was not looking for any kind of relationship. It all started with a “like” on his photo on Instagram. He then returned the like on one of my photos and we went back and forth for a few days until I finally broke the ice and messaged him. (yes I went after him). We exchanged numbers and that day he asked me to come to a party as his friends house that night. I was at the river in Richmond with my girlfriends and rushed home as fast at I could to get ready that evening with stomach full of butterflies. He picked me up in this very modded out car which I thought it was the coolest thing considering my small town was full of jacked up trucks and nothing like that. We went to dinner and that night we went to his friends house for that party and I knew, as crazy as it sounds that I literally was looking at the love of my life on our first date. We clicked INSTANTLY and were absolutely inseparable from that night on. We talked every single day, all day for about 3 months before he asked me to be his girlfriend. He asked me with red roses and a card on June 14th, 2014.

how they asked

Caleb and I moved in together June 2015. That fall we both went for the very first time with another couple to Carter’s Mountain Orchard to pick apples. That one fall began a tradition of us going every year. This year, would be the best year of my life this far. Our mutual friend, Chelsea who is an amazing photographer made a Facebook status that said “I really want to go apple picking this year, maybe Carter’s Mountain? and winery hopping. any of our friends want to join along? pictures will probably be a thing.” so of course I jumped onto that!! Little did I know, Caleb and Chelsea were planning this all along to get me to think it was another trip just like every year with another couple. The weather on that day, October 15th, 2017 was absolutely perfect. We were snapping random pictures in the orchard and I didn’t think anything of it, I mean she’s a photographer and loves to take pictures. They made a code word “The lighting is good” so he knew that it was a good setting to ask. She said that code word and he dropped down on one knee with the most gorgeous ring I have ever seen and said the sweetest things to me, then asked me to marry him!! My best friend Emily had known this whole entire time, planning with him for months for this day. She even helped him pick out the ring! She drove all the way up to the mountain and surprised me that day, minutes after it happened. It was the most amazing day of my life thus far.

We went winery hopping afterwards and celebrated our engagement all day. I couldn’t have thought of a better way.

Special Thanks

Chelsea Rose
Emily Holt |