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

After realizing Pat left his police badge at home, Jimmy convinces Kenny and Shannon that he should use Pat’s badge to pretend he’s a police officer so they can receive free perks around town. Meanwhile, when Pat tells Eileen about an upcoming date he’s going on, she takes matters into her own hands when it comes to a potential suitor in her dating life.

We step into the O’Neals’ messy dating lives as Eileen and VP Murray’s secret dating life is about to be unraveled, Kenny jumps into the world of gay dating apps but feels discouraged after not getting enough swipes to the right, and Jimmy goes too far to declare his love for Lacey. Meanwhile, Aunt Jodi meddles with Shannon’s love life after mistakenly thinking she needed her help.