When they first met in Mrs. Norley's algebra class, Cassidy and Kady each had very different trains of thought, but they both inevitably parked in the same station: "I want to follow this wonderful crazy person around for the rest of my life." Cassidy doesn't remember their first conversation, only the overwhelming sense that Kady was the kind of person that she wanted to be around, even if that meant braving the insanity of social interactions with strangers and the growing pains of newly forged friendships. Kady remembers exactly how her first conversation with Cassidy went; she was creating an intricate beaded bracelet under her desk while she was supposed to be listening to the teacher lecture. Kady swears that that was the moment that she fell in love, but Cassidy maintains that what she was probably feeling was closer to fascinated confusion and the butterflies in her stomach went up the wrong tube.

For approximately three of the six years that Kady and Cassidy had been together before they got engaged, they knew that they wanted to get married, but the time was never right. Up until 2021, Cassidy was away at college while Kady entered the workforce and the entire time, they both stressed about how they would propose. Who would get the honor of popping the question? Would it be on a date? Out in public? Would it be dramatic? Would they have a photographer? Each question left them stressed and avoidant, deciding to put off marriage until they'd been living together for at least a year, with stable jobs and a mortgage and 3 pets and medical insurance in their own names. Their proposal ended up actually happening in a cluttered dining room after less than a year of living together. Cassidy simply showed Kady a couple ring choices on Etsy with a very pragmatic, "I can't choose and you deserve nothing less than what will make you happy, so I need you to pick your favorite." Cassidy picked her own ring a week later and they each got down on one knee in that same dining room and agreed to live life with each other in the way that would make them happiest, not the way in which things are "meant to be done".