Amelia had just moved to Charleston and was trying to make new friends. Two acquaintances (now friends) invited her to join them on their friend's boat one weekend. Sure enough, it was Drew and his MasterCraft. They somehow convinced Amelia to water ski for the second time ever right after driving by an alligator. Drew and Amelia bonded over their love for the water. Amelia quickly became Drew's first mate that season, as he coached her to wakeboard and drive a ski boat.

Amelia and Drew typically spend their weekends boating and skiing. On a sunny June weekend, Drew suggested that prior to putting the boat in the water, they visit a Trappist Monastery along the river where they boat. The monastery is known for its gardens and beautiful scenery, which is open to the public. Drew also recommended dressing up for the occasion, to which Amelia obliviously obliged, not questioning Drew's choice of nicest shorts and polo. Drew had an idea of where he wanted to propose to Amelia, but found the area crowded (all of 4 people) upon arrival, so they continued to tour the grounds. They soon found themselves in a secluded area with a beautiful view of the water through the trees. Here Drew surprised Amelia and asked her to marry him. She said Yes!