Kevin and Serena grew a lot closer through the beginning of medical school thanks to their mutual friend, Brenton. He connected several people to the same study group, where Kevin and Serena began to know each other. During a bowling outing with friends, Kevin made a bet with Serena that he could beat her at bowling, and loser would treat the winner to 3 meals.

Kevin lost. To this day, he claims it was on purpose to have an excuse to take Serena out on dates. Serena thinks he is just bad at bowling, but it was sneaky and sweet.

They dated throughout medical school. Together, Kevin and Serena survived the challenges of medical school, three board examinations, a pandemic, and a residency match process leading them to Cleveland, Ohio.

In December, Kevin and Serena went on vacation to Maui, Hawaii. Kevin planned a multi-day scavenger hunt, filled with fake-out possible engagements, including a luau, a road trip, hiking (complete with Kevin kneeling on the ground to tie his shoe), and a helicopter ride. By the end of the trip, Serena was fairly convinced the engagement would not happen this time.

On December 15th, 2022, Kevin took Serena to the beach behind a waterfront restaurant while they "waited for their table" and proposed.

She said "Yes".