It was the day of Madison's high school graduation party and Kiera ended up bringing Kelsey along. After the party was over, Kelsey and Winston immediately exchanged numbers and were texting each other nonstop. With Winston at Kingswood Oxford and Kelsey at Hamden Hall, they would find ways to bump into each other when their schools would play each other in football or basketball. From there, they would go on movie dates, meet each others families and eventually both graduate from St. John's University. After graduation, their life together took off and they began to travel the world.

It was the dinner of Kelsey's dreams! Wine, friends, good food, all that was missing was...the ring! Winston had planned the perfect surprise and just as they sat down at the table he realized the most important piece of the night was still hidden back at the hotel. Thank god for long strides and with a good distraction he was able to recover without Kelsey noticing a thing. After the dinner concluded, Winston made a toast that would end up being the question of a lifetime.