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.