Tommy and Kelsey can't pin down exactly when they first met. They ran in similar circles in secondary school and at church, but Tommy first noticed Kelsey's sweet and bubbly personality during Junior year of high school. He decided to ask Kelsey to the fall Homecoming dance, but she was so surprised by his impromptu invitation that she initially turned him down and requested that he ask again with more ceremony (in keeping with prom-posal tradition). After the dance, Kelsey and Tommy continued their on-and-off flirtation for several months until the Lakeville South Chorale spring break tour to Austria. Throughout their travels and many performances, Kelsey discovered how much she admired Tommy's passion for singing, his quirky sense of humor, and his dashing good looks. On the plane ride back to the USA, Kelsey managed to switch seats with a friend so she could sit next to Tommy. They made their relationship official on April 19, 2013 after one of the performances of Lakeville South High School's Les Miserables, in which Tommy and Kelsey were both chorus members. Tommy was Kelsey's first kiss.