Hannah, a 24-year-old aspiring writer living in NYC, is blindsided when her parents cut her off financially. Subsequently fired from her unpaid internship, she seeks comfort from Adam, the eccentric actor she sometimes sleeps with when she can get him to respond to her texts. Meanwhile, Hanna's best friend and Type-A roommate Marnie hosts a dinner party for their bohemian British friend Jessa, who has returned from who-knows-where to move in with her younger, 'Sex and the City'-obsessed cousin Shoshanna.
Jessa and Marnie struggle with issues surrounding an appointment as a women's clinic and Hannah deals with an STD scare.
Marnie meets a potential romantic match and Jessa finds a job. Meanwhile, Hannah confronts an ex-boyfriend from college.
Hannah gets stressed when she receives a text message from Adam and, while babysitting, Jessa gets distracted. Meanwhile, Ray and Charlie get nosy and Shoshanna gets together with a guy she met at camp.
Fed up with her boss' behavior, Hannah decides to make a move on him. Meanwhile, Marnie wonders about her relationship with Charlie and and Jessa wants to ensure she has the last word.
Hannah visits her parents in Michigan for their 30th anniversary, and winds up going on a date to a fund-raiser for a local family who suffered a tragic loss.
At a raging party in the Bushwick section of Brooklyn, Hannah sees a different side of Adam; Jessa lures the sender of an anonymous text message; Marnie finds out what Charlie's been up to for the past two weeks; and Shoshanna gets a hand from Ray when she needs it most.
Jessa and Marnie meet an eligible bachelor who is not all he seems and Hannah gets more involved in Adam's life.
Hannah's lack of income forces her to take a job at Cafe Grumpy and her mood is not improved by discovering a former classmate has achieved literary success. Meanwhile, Jessa's former boss confronts her and Shoshanna starts internet dating.
While Hannah questions whether she should be with Adam, Jessa throws a mystery party.