Tennessee boy meets Florida girl. Skylar was just moving to Florida from Tennessee to start his college education and Jessica was starting a new semester, both at Santa Fe College in Gainesville, FL. Still not have met each other, they were both invited to a "start of the school year" party which was in the apartment complex that Jessica was living in at the time. Jessica was playing beer pong with one of her college roommates when Skylar walked in in his yellow Polo button down, khaki pants and brown Cole Haans. They caught eyes and said hello to each other but then continued doing their own thing. Skylar then came back up to Jessica, introduced himself then asked if he could do a “celeb shot” for her beer pong game, which he did but missed so that was the end of that encounter. Jessica and her roommates were planning to have a party that coming Friday so she decided to invite his roommate, not knowing they were roommates at the time. Friday came and walked in Skylar, in a different colored button down and his brown Cole Haans. Again, he walked up to Jessica saying hello and from there, the rest was history. Jessica’s best friend Forest was in town that weekend and after seeing their first encounter that night, she instantly knew that Jessica needed to get to know this Tennessee boy. Over the next 8 months, Skylar and Jessica became the best of friends. Then on Friday, March the 13th, he asked her to be his girlfriend.

Jessica’s family had planned their Christmas trip to return to her extended family’s mountain house in Wyndham, New York and Skylar knew this was the perfect timing to start their happily ever after. He had attended this same trip two years prior. While skiing and snowboarding together, Jessica and Skylar stopped at an overhang to take a picture with the little town of Wyndam in the background. They both thought the views were breathtaking and little did they know, this would be the spot Skylar asked Jessica to spend the rest of their lives together. Fast forward to the big day, while riding the lift up the mountain, he realized that this said overhang was no longer there. Change of plans, he found a new overhang which he decided was where he was going to pop the life changing question. Everyone but Jessica was aware of what was about to happen. While Skylar and Jessica were riding the lift up together to go down a slope, her brothers Christopher and Eric called her over to the overhang to take a sibling picture together. Skylar and Jessica were up next for a few pictures to capture the moment. While taking their pictures, Skylar asked Jessica to turn towards the beautiful view. He began expressing his love for her and in this moment, Skylar got down on one knee asking her to be his wife. Jessica may not remember all that was said due to being overcome with excitement and happiness, but most importantly she knows that she said YES! Skylar truly made this moment special by having her brothers present during the proposal. After skiing down the slope, she found her parents, Skylar's parents and some extended family awaiting their arrival to congratulate them. The start of their engagement was congratulated with Ring Pop cupcakes and champagne.