Sam's newfound self-confidence is shaken when she learns her new boss is a blast from the past. Meanwhile, Felicia errs in how to congratulate her boyfriend on his promotion. And Olivia makes a life-changing decision.
In flashbacks to her dad's shiva, Sam is at odds with Carol while grappling with their own grief and dealing with her judgy Aunt Alice. In the present, Sam and James reunite at an AA funeral and fall into old patterns.
For the first time in forever, with a new job and a new potential love interest, Sam thinks she has a life worth celebrating and throws herself a birthday party. Brit tries to convince everyone that she and Joel have the "perfect divorce."
On her wedding day, Brit's jitters lead her to make an unexpected decision. Carol and Bob take their relationship to a new level. Sam learns the truth about James and is shaken to the core about what her future might hold.
Sam questions if she can move on at work from her old self while also trying to navigate a relationship with a "normie." Carol snoops around Sam's room and makes a terrible discovery. Joel and James have a night out.
At Olivia's baby shower, Sam is forced to accept that she needs a new sponsor but doesn't hit it off with Olivia's suggestion; Carol visits Felicia and the two discover they have more in common than they thought.
Sam faces her hardest challenge yet: avoiding alcohol on St. Patrick's Day in Boston; Brit gives Sam an unexpected chance to rekindle their friendship; James and Mindy track down his lost keys while battling St. Patrick's Day temptations.
Sam and Alex prepare for their first romantic weekend away while Brit struggles to cope with singlehood in surprising ways. Elsewhere, Carol reluctantly tries Al-Anon, and James seeks help from an unlikely source.