On the first warm day of spring following an endless Chicago winter, Eileen decides it's time to get a fresh start in her life by applying for her first job since her kids were born. Shannon ultimately overhears her mom's plan and riles up the rest of the family after misinterpreting Eileen's true intentions. Meanwhile, Pat realizes he might not be ready for the single life just yet, even though his patrol partner, Archie, thinks otherwise. And as Kenny wonders who he will date next, Jimmy takes it upon himself to help him explore the newfound world of online dating.