Fiona spends her summer with a new guy and bartending, while Debbie runs a daycare at their home. Meanwhile, Kevin realizes his extended weed-growing left him with a huge electrical bill and Frank borrows his youngest son Liam to help him pay a debt.

As Sheila conquers her agoraphobia, a worried Frank finds a new financial plan in fellow bar patron Dottie, whose declining health and city pension make her an ideal match; Fiona juggles her job, the kids and her burgeoning love life, and Jasmine tries to help by setting up Fiona with a sugar daddy.

Fiona hopes her moral compass isn't leading her astray when she reconnects with her married high school crush, but when she finds an abandoned purse with over five hundred dollars inside, she assumes her luck is finally changing.

Fiona deals with the consequences of sleeping with Craig when his angry wife shows up at the door; Debbie develops a stress-rash and Fiona wonders if she's putting too much responsibility on the kids; Sheila has made it all the way to the hair salon and Frank realizes his days in the Jackson household are numbered.

Frank tries to claim Eddie\'s insurance benefits and pension, despite being a prime suspect in his passing; Fiona attends a ritzy wedding with Richard and lies about her background; Lip is devastated by Karen\'s rejection; Carl rents Frank\'s room to a hooker.

Grammy Gallagher shows up on a medical furlough and tries to track down a former meth lab protege that owes her money; Sheila plans Karen's wedding reception; Fiona double dates with Steve and his Brazilian girlfriend, and discovers that Steve is married; Ethel reacts to Clyde's passing; Frank discovers the identity of Eddie's insurance beneficiary.

Fiona walks into Steve and his new girlfriend Estefania on Jasmine's end-of-summer blowout. In the meantime, Frank tries to get rid of Grammy, while Fiona enjoys her company. Lip prepares a prenup for Jody and Karen.

With Grammy near passing, Frank exits the house but walks in on Ian and Mickey locked in passion at the Kash and Grab; when Lip drops out of school, Fiona proposes a deal where they both earn their diplomas, but Lip acts out and gets himself expelled when he realizes that Karen plans to sell their baby to the highest bidder.

Monica shows up again and Frank tries to get his hands on the inheritance. Meanwhile, Jody and Sheila think they are haunted.

Fiona starts to plan for her future now that Monica is back but her reprieve may be short-lived as Monica falls apart, spends the squirrel fund and gets arrested; Steve conspires to reunite Estefania with her true love so that he can be with Fiona; Lip and Ian learn the true identity of Mandy's baby; Sheila takes in a homeless crack addict.

It's a typical Gallagher nontraditional Thanksgiving that includes a sleeping attempt by Monica, Carl shooting a bald eagle, and Karen going into labor; Steve agrees to allow Estefania's boyfriend to steal his identity; Lip sleeps with a businessman named Ned; Frank tries to get his share of his mother's money from his brother Clayton.

A lonely Frank schemes to break Monica out of the psychiatric facility. Jimmy earns his way back into Fiona's good graces and asks her to meet his family while Ian runs into Ned again. Eddie's insurance check arrives.