In the season five premiere, it's summertime again in Chicago. Fiona balances her job at Patsy's Pies with a crush on her older boss, Sean (Mulroney). After saying goodbye to college and Amanda (recurring guest star Nichole Bloom), Lip heads back home where he struggles to fit in with his old Southside friends. But he's not the only thing in the neighborhood that's changing. With realtors buying up property, there's even a new trendy yoga studio that's popped up. Meanwhile, Frank, still recovering from his liver transplant, is living at Sheila's and working on a secret project in her basement, while Sheila (Cusack) works upstairs to get rid of a problematic Sammi (Bergl) and Chuckie (guest star Kellen Michael).
Fiona is finally officially off house arrest, while Lip starts his first day of work for Tommy (recurring guest star Michael Patrick McGill). But manual labor turns out to be much harder for Lip than he thought…and the brutal hazing from his co-workers certainly doesn’t help. Meanwhile, a manic Ian plans his revenge against a homophobic military funeral protest with Mickey and Mandy Milkovich (recurring guest star Emma Greenwell).
The gentrification of Chicago's Back of the Yards neighborhood continues as Frank enlists Carl to scare off potential investors who are buying up more property in the neighborhood, while pleading with Sheila not to cave and sell her home. Meanwhile, Frank sets the owner of a junkyard up with his daughter, Sammi under shady pretenses in exchange for new brewery equipment.
When Frank arrives at Lou's to pick up his six-figure insurance settlement, he's shocked to discover that he's already collected it. Meanwhile, Lip visits Amanda and her family at their luxurious house in Miami.
Fiona and Gus must navigate the awkwardness of their quickie wedding. But Fiona's plans to announce her marriage at a family dinner become unraveled when her coworker Jackie OD's on heroin. Meanwhile, Frank, who promised an irate Sammi a new trailer once he got his insurance money, avoids her by staying with the still grieving family of his donor liver.
Fiona is thrown into chaos by the return of Jimmy/Jack/Steve, but she must deal with an even larger crisis first as Ian, in a full psychotic break, steals Mickey and Svetlana's baby, Yevgeny, and takes him along on a road trip. But Jimmy is relentless in his pursuit of Fiona who, despite her recent nuptials, eventually gives into their fiery chemistry and long history.
William H. Macy
Frank Gallagher
Emmy Rossum
Fiona Gallagher
Ethan Cutkosky
Carl Gallagher
Shanola Hampton
Veronica Fisher
Steve Howey
Kevin Ball