Sam embarks upon her first terrifyingly personal hook-up as a sober person with the help of Felicia, who has big plans to jump-start Sam’s dating life. Meanwhile, Carol “accidentally” plants a small seed of doubt in Brit’s mind about Joel.

A public flame-out forces 20-something alcoholic Sam to move back home with her overbearing mother, Carol. Surrounded by all the triggers that made her drink, Sam tries to move past her worst self and figure out her best self. Kinda.

An awkward run-in with her former best friend and her ex inspires Sam to own up to her past mistakes, both emotionally and financially. Meanwhile, as she resets her relationship with her mom, Sam is horrified to learn Carol is dating.

Sam tries to win over Brit by making an amends at her birthday party. Unfortunately, Sam wasn’t invited and neglected Felicia. Meanwhile, when Sam’s probation officer stops by, Carol struggles to explain Sam’s “situation” to her friends.

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 scores a victory when she lands a job interview in New York with an unlikely ally, only to discover how scary it is to write while sober. Concerned that her daughter needs help, Carol breaks a boundary and introduces herself to Olivia.

Sam and James travel to New York. While there, Sam is confronted with memories of who she was before sobriety and must decide whether she can risk being Old Sam again. Olivia and Stephanie take an important step in their IVF journey.

In this flashback episode, an inebriated James meets a drunken “Katrina” (Sam) in a bar on Thanksgiving. After getting kicked out, the two embark upon their own one-night holiday celebration. James’ time with Sam spurs him to make a change.

After celebrating a milestone with a bang, Sam decides it’s time to make amends with Carol. When a fight with Joel makes Brit reexamine the future, she turns to an unlikely ally: Felicia. Meanwhile, James conceals a destructive secret.

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.

After Sam learns that Carol has invaded her privacy, the two have an explosive fight, leaving Bob to try to mediate. And just as things are going well with Peter, Felicia gets an unwelcome visitor from her past.

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.

Sam gets the opportunity to interview Bob the Drag Queen, but she sabotages her chance when she and Alex have their first fight. Meanwhile, Carol is forced to take her Al-Anon program seriously, and James tries to reconnect with Mindy.

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.

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 struggles with whether or not to come clean to Alex about recent events. Meanwhile, James finds strength in his community, and Bob fights for Carol.

Sam continues her search for her higher power. Brit and Joel throw a divorce party. Felicia considers next steps in her relationship with Peter.

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'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.