Once upon a time, Carlye was scrolling through the dating app OkCupid when she stumbled upon a picture of a cute guy named Derek. She was charmed by his blue eyes and sweet smile, so she swiped right and was pleased to discover that they had matched. Although she was not usually so bold on the dating app, Carlye decided to send the first message to Derek. She put much thought into her initial message, and she finally settled on making a joke about Derek's horrible taste in baseball teams (she had seen a picture of him wearing a Red Sox hat in his profile). Derek took the playful banter in stride and reminded her that the Red Sox had just won the World Series the year prior. Putting their differences aside, the two began talking and never stopped. A few weeks later, they had their first date at Trackside Brick Oven Pizzeria in Wallingford. Carlye and Derek spent the evening conversing over topics such as the final season of Game of Thrones, their favorite Disney movies, and many other topics all while enjoying a large pizza. Derek was enthralled by Carlye's witty and sometimes dark sense of humor and Carlye admired Derek's warm, kind-hearted personality. By the end of the night, both Carlye and Derek agreed that they would meet again.

A few days before Derek proposed, he suggested to Carlye that they go out to Trackside Pizzeria for dinner on Saturday since they had not been there in a while. Considering they had not been there since their first date four years earlier, Carlye found this suggestion suspicious. However, when Saturday came, unforeseen circumstances (a flat tire, a touch of dehydration, and an unexpected early closing from the restaurant) had them changing their plans. The two went to Sicily Coal Fire Pizza in Middletown instead, and since Derek seemed completely unconcerned with the abrupt change of plans, Carlye no longer suspected a possible proposal. The two sat at a table right next to the hostess stand and spared no expense in food and drinks. While eating a pizza practically the size of their table, Carlye indulged in one of her favorite date night activities: asking Derek cheesy first date questions. This time she asked him what his hopes and dreams were. Derek, with a mouthful of pizza, told her to ask him again later. After dinner, Carlye repeated, "So, what are your hopes and dreams?" Derek smiled sheepishly and chuckled, "Well, I do have one hope and dream." Carlye watched, her heart beating frantically, as Derek stood from his seat and promptly bent down on one knee. He took a ring from his pocket and asked, "Will you marry me?" Carlye said yes, half-sobbing, half-laughing as the hostesses behind Derek jumped up and down, screaming, "Congratulations!"