In the summer of 2021, after planning to start with a different airline company in Texas, Kevin got a job offer to fly with Delta Connection, which required him to move to Minnesota for several months of training. He was able to enjoy some of the beautiful Minnesota summer while living in a hotel and studying day in and day out. In the midst of learning how to fly a CRJ-900, he somehow found the time to spread his wings and meet some locals. Alyssa spent 5 (cold) years living in Minnesota for her surgical training at Mayo Clinic. During her final year there, she was excited to dedicate a lot of time to her job and take in everything that training at Mayo had to offer prior to moving to Chicago for pediatric otolaryngology fellowship. When she was least expecting it and began to embrace the idea of waiting until she was in Chicago to meet someone, she met Kevin. Kevin had a rather unoriginal pick up line ("I wish you were my doctor [heart eyes]") but there was something about him that drew Alyssa in. They met at a coffee shop near the MSP airport as Alyssa was headed out of town for an ENT conference in Los Angeles. Kevin says that he knew she was "the one" as soon as she stepped out of her car. Alyssa knew as soon as Kevin, a man from Kentucky, told her that he was a Patriots fan. Somehow she had found a unicorn; a southern boy living in Minnesota who shared her same love for Boston sports. At the end of their first date, despite both being nervous to reveal this information, Kevin shared that he would soon be based in Cincinnati, and Alyssa that she would be moving to Chicago in July. Although the possibility of a long distance relationship loomed, neither were discouraged. The entire time Alyssa was in Los Angeles, she was texting and talking with Kevin. As soon as her plane landed back in Minnesota, she was on her way to see Kevin again. This continued and blossomed in the days and weeks that followed. They both celebrated the big and little wins as Kevin started his first commercial airline job and Alyssa wrapped up residency. Before they knew it they were moving to Chicago together with their cat child, Stella.

During a trip to Alyssa's hometown in Massachusetts, Kevin asked Alyssa's parents for their permission to marry her, and of course they said yes. A few months later Kevin and Alyssa were back in her hometown for her sister’s baby shower. At the end of the shower, Alyssa's dad said he wanted to show her a new addition to the local library, the same library she used for all her book reports as a child and spent days in studying for the MCAT and USMLE exams. He walked her over to the library and Kevin was standing outside with music playing and rose petals on the lawn. When he got down on one knee, it was an immediate yes from Alyssa.