A day that changed Kasey and Riley’s lives forever. This day was the day they matched on the social media app, Tinder. Although Kasey’s grandmother Ruth has always warned her to never date a Midshipman at the Naval Academy, she took a chance on Riley and decided to meet him for a first official date! After waiting at the table for his date to show for about 40 minutes, Riley was ready to accept the fact that he had been stood up because he was not aware of Kasey’s notable ability to be punctual. Nevertheless, she strolled into the restaurant with the poise and confidence of a true Annapolitan unaware of how close Riley was about to call it quits. After this date, they were more open with each other than they had ever been with anyone else they had endured a first date with. The couple knew that there was something special between them. Not long after this, Kasey and Riley took the plunge and became an official couple March 16, 2017.

Riley wanted to propose to Kasey in a way that would be private and meaningful for his future bride. He was aware of how shy Kasey is around people and would be frazzled if the proposal happened in a flashy and public way so he decided to keep it “low key”. He decided that he would take Kasey to their old spot where Kasey would come visit him when he was trapped on the Yard and share a meal together. On August, 24 2019, Riley asked an clueless Kasey if she wanted to go on a picnic. He smuggled the ring into the bag of food and asked one of his old friends that doubled as a photographer to take pictures of them from afar. After being so nervous he could barely stomach his first bite, Riley got on a knee and popped the question. Kasey quickly looked around and noticed an elderly lady sitting on the bench next to them watching and immediately broke into a sweat and a blush. Needless to say, Kasey could hardly form any words due to her shock which left Riley on one knee long enough to question if she would say yes. She eventually gave him a solid and “confident” ok which was good enough for Riley. They quickly finished their picnic and raced to tell the world that their lives were going to change forever!