Ep 4. It's a Shame About Ray

Hannah and Ray go on a road trip to pick up a chair that Hannah purchased on Craigslist. The two get into a heated argument about Ray's recent breakup and Hannah's attitude towards it. Meanwhile, Shoshanna and Jessa spend the day together and attend a warehouse party where Jessa makes the acquaintance of a mysterious stranger. Marnie receives a job offer from Booth Jonathan, whom she had a brief fling with in season one, and struggles with whether or not to accept it. Adam invites Hannah over for a day of alone time but is interrupted by Caroline, his sister, who has just been released from rehab.

The episode begins with Hannah frantically calling Ray to come pick her up after her bike was stolen. Ray begrudgingly agrees to go get her and they head back to her apartment where she shows him the most recent addition to her apartment, a couch from Craigslist that she loves. However, she still wants a chair to complete the set and after browsing online, finds one in Pennsylvania that she insists on getting. Ray agrees to go with her to pick it up, prompting a rocky road trip where they argue over his recent breakup with his girlfriend and Hannah's insensitivity towards his feelings.

Meanwhile, Shoshanna and Jessa spend the day together and attend a warehouse party. Jessa attracts the attention of a mysterious artist, Thomas-John, who she hits it off with over shared interests in art and drugs. They end up spending the night together and Jessa is smitten with him. Shoshanna, on the other hand, has a panic attack while drunk and ends up stuck in a closet until Marnie comes to her rescue.

Back at Hannah's apartment, Marnie receives a job offer from Booth Jonathan, a highly successful artist whom she had a brief fling with in season one. Marnie is taken aback but ultimately decides to consider the job offer seriously. She later meets with Booth at his studio where they discuss her role in his new project. The meeting is tense but ends with Booth offering Marnie the job.

Finally, Adam invites Hannah over for a day of alone time, but his plans are interrupted by the arrival of his sister, Caroline, who has just been released from rehab. Caroline is unpredictable and erratic, and Hannah is uncomfortable around her. The day ends with Hannah and Caroline arguing, leaving Adam to mediate.

The episode concludes with each character feeling uncertain about their future- whether it be accepting a job offer or deciding whether or not to pursue a new romantic interest- and the implications of these decisions on their relationships with one another.