Josh first met Kelsey as the lead carpool driver for a group of new teachers in Baltimore. They instantly got along well bonding over sarcasm and burping contests (Josh is still yet to win one). They have been on a number of adventures together as Kelsey helped guide Josh west of the Mississippi for the first time. She also receives credit for getting Josh to switch from cargo pants to jeans and for introducing him to the drinking game Boom. Kelsey is in her 11th year of teaching and currently resides in Milwaukee.