When Hannah finds out that her parents have decided not to financially support her anymore, she doesn’t take it lightly. She’s two years out of college, but she still can’t manage to pay her bills without their help, mostly because all she has at the moment is an unpaid internship. She lives with her BFF, Marnie, who’s dating her college sweetheart, Charlie. However, she’s not that attracted to him anymore and contemplates the idea of moving on.
Meanwhile, Jessa just arrived in New York and is rooming with her cousin Shoshanna, the one who’s still a virgin and enjoys putting together vision boards. Jessa thinks she’s pregnant, but later finds out it was a false alarm. And by later I mean while she was hooking up with a random stranger and blowing off her abortion appointment.
The girls go through a lot of adventures during the course of the season. Hannah asks for a full-time position, but she’s let go instead. We meet her friend with benefits, Adam, an oddball of a guy, who will later become her boyfriend. Shossanna loses her virginity to Ray, Charlie’s best friend. Marnie breaks up with Charlie, but finds herself pining after him when he moves on too soon.
However, the biggest surprise of the season comes from Jessa. After engaging in an emotional affair with the father of the girls she babysat, she gets hitched in the very last episode with another guy, during a surprise wedding.
Fed up with her roommate, Marnie decides to move out. Adam and Hannah get into a terrible fight and break up.
While the beginning of the season is pretty bright, lining up new challenges for the foursome, it goes terribly dark sometime during the middle. Hannah starts off in a good place: she’s now roommates with Elijah, her ex-boyfriend from college, who’s actually gay. She takes on some freelance work, does cocaine in the name of art, hosts a “grownup” dinner party, and finally realizes that she wants to be happy.
However, after she gets an e-book deal, she starts to show symptoms of OCD, which only get worse towards the end of the season. She cuts her own hair and hides her anxiety from her parents, while facing a lot of pressure from her editor to meet her deadline. Meanwhile, Adam is dating another girl, Natalia; despite this slight little detail, he and Hannah reconnect at the end of the season.
As for the other girls, Shossanna begins to date Ray and they basically end up living together, but their relationship eventually deteriorates. Jessa’s marriage falls apart and she’s MIA by the season’s end. As for Marnie, she loses her job and becomes a hot mess. She has sex with Elijah, which causes an even larger drift between she and Hannah, so she’s basically navigating season two with no boyfriend, no job, and no BFF. She briefly dates an artist, but it doesn’t work out. Then, she tries to reconnect with Charlie, who’s now the owner of a successful startup, and the two rekindle their relationship in the last episode.
At the beginning of the season, Marnie is recovering after yet another breakup with Charlie, Hannah is much better due to Adam’s help, Shossanna is reevaluating her life following her breakup, and Jessa is in rehab. Hannah, Adam and Shoshanna go on a road trip to check her out and bring her back to New York.
Hannah is living with Adam now, but their routine is disrupted when Adam’s sister moves in. Our protagonist’s life further complicates when her editor dies and she finds out that her e-book deal won’t pan out after all. She takes a job at GQ, but she ends up quitting in order to devote herself entirely to her artistry. When Adam is cast in a Broadway show, their relationship starts to go south, as he feels the need to spend more time by himself. At the end of the season, Hannah finds out that she was accepted in a prestigious writers’ workshop in Iowa and decides to enroll and move away.
Elsewhere, Jessa spends the season struggling with her addiction. She eventually gets a job working for an artist, Bedelia, and agrees to help her kill herself. During the act though, Bedelia changes her mind, so Jessa calls 911.
Marnie starts to sleep with Ray, but he eventually calls it quits. She then meets Desi, a musician who seems interested in her voice. The two start to collaborate, and Marnie slowly falls for him, despite the fact that he has a girlfriend.
As for Shosshanna, she ends the season on a low note. Besides finding out that she won’t graduate, Marnie also tells her she slept with Ray. Shosshanna begs Ray to take her back, but he politely refuses.