In the Season 2 premiere, despite her breakup with Steve, Fiona tends bar at a local hotspot with Veronica, hangs out with a successful young business executive, and enjoys her youth; Debbie runs a daycare with Carl; Ian takes over at the Kash and Grab when Kash leaves town; Lip runs a Little League book and helps Kev out with their annual ice cream/pot truck; despite Eddie's disappearance, Sheila takes small steps to finally leave the house; Frank loses a bet and surrenders Liam as collateral.
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; Veronica takes some old folks from the home on an excursion; Lip worries about Karen's growing relationship with Jody; Ian tries to land a recently released Mickey a job at the Kash and Grab; Debbie wants her own room; Carl moves into the van.
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; Frank is willing to do just about anything to stay in Dottie's good graces, even marry her; after Harry's passing, Debbie becomes obsessed with death; Kevin thinks about buying the Alibi; Lip meets with a colonel to glean information for Ian about West Point; Jody asks Frank for Karen's hand in marriage.
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; no longer having sex with Karen, Lip tries to dig up dirt on Jody; Ian continues on the path to West Point; Carl house-sits with his friend, Little Hank; Ethel meets Malik, a boy on Kevin's youth basketball team.
Frank tries to claim Eddie's insurance benefits and pension, despite being a prime suspect in his death; 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 to find her old meth lab pal who owes her money.
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.
Frank discovers Ian and Mickey's relationship. Meanwhile, Jody and Sheila take care of Grammy who is dying. Lip wants to leave school and Fiona tells him about her plans to go back and get a GED.
Monica shows up again and Frank tries to get his hands on the inheritance. Meanwhile, Jody and Sheila think they are haunted.
While Monica stirs things up, Fiona tries to plan her own future.
While Fiona's planning a nice Thanksgiving, Monica's becoming more depressed than ever. Frank realizes that it's time to get her back on her meds, but he might be too late.
In the season finale, Jimmy/Steve has earned his way back into Fiona's good graces and wants her to meet his family. And Frank plans to break Monica out of the psychiatric facility.