Michael and Jess met each other in October of 2017. They both rowed at the Naval Academy, Michael for the Heavyweight team and Jess for the Women's team. Although they didn't talk much at the boathouse, they would sometimes walk the mile back from the boathouse to dinner together. Michael says that he remembers Jess' laugh that could be heard throughout the boathouse, and Jess says that Michael was the sweetest and funniest person she met.

Although Michael and Jess had many study dates that were definitely not dates according to Jess, Michael "officially" asked Jess out on March 5th, 2018. On their first date, Michael "accidentally" took Jess out to the most expensive Italian restaurant in Downtown Annapolis. He balanced the next date by ordering pizza and watching Talladega Nights in his room.

Best. Day. EVER! It was an extremely cold (11 degrees) morning in Angel Fire, NM. If you know Jess, you'll know that she is not a morning person. That morning, Michael woke Jess up to watch the sunrise. He put on her coat and beanie while she was still half-asleep, and made some cinnamon rolls and coffee. They were bundled up (OUTSIDE) on the porch, watching the sun come up over the mountain, when suddenly Michael says "I can't wait any longer" and starts getting down on his knee. Jess is obviously very confused because she is still sleepy, but starts bawling once she sees the ring. She can't really remember what Michael said because she was crying, but she is sure it was great. Jess managed a "yes!" in between sobs, and it was the best morning they ever had.