Frank’s latest sexual escapades get him into trouble with the Hopkins Academy PTA. Fiona struggles with her decision to bail Ian out of jail, while he continues his Gay Jesus antics inside. Lip juggles taking care of Xan with a potential romance. Debbie fights for equal pay at work, and Carl has to prove himself at military school. Kev and V have trouble with the twins without Svetlana.

Fiona makes a play for a risky investment opportunity, ignoring Ford’s advice. Frank discovers the financial incentives of local politics. Carl bolsters his West Point application in unexpected ways. Debbie struggles to find allies in her battle against sexual harassment. Ian is overwhelmed by the growth of the Gay Jesus movement. Kev and V try to find the perfect preschool for the twins.

Frank faces obstacles in his new role as a campaign manager. Fiona prepares to close her real estate deal. Carl enlists V to help him get a West Point recommendation from a congressman. Xan’s medical emergency puts Lip in a compromising position. Debbie gets closer with her partner in crime. Ian embarks on a spiritual journey.

Election day puts Frank and Fiona in a head to head battle as they each try to round up votes for their candidates. Lip has to make an important choice about Xan’s future. Debbie gets in over her head with Alex. Carl’s killer instinct is put to the test. With his trial looming, Ian struggles to decide how to plead. 100th episode!

Frank meets his match in a fellow participant in the Hobo Loco competition. Fiona has a dark encounter at Patsy's that scares her into cleaning up her act. Debbie throws herself into home improvements as she gets closer with Kelly.

The finals of the Hobo Games have arrived, and Frank faces off against his friend and greatest opponent while Ingrid grows anxious about his commitment to their future family. Lip prepares to officially adopt Xan, but his plans collide with Fiona’s partying. Debbie starts developing feelings for someone surprising, and Carl excels at the shrimp shack.

When a blackout hits the South Side, Kevin and Veronica come up with a plan to bring the neighborhood together. Carl grows suspicious of Debbie’s attempts to get closer with Kelly. Fiona receives guidance from an unexpected person and Lip has to deal with the fallout from Xan’s DCFS visit.