Aspiring writer Hannah is blindsided when her parents cut her off financially. Hannah's best friend and roommate, Marnie, hosts a dinner for their friend Jessa, who has returned to NYC to move in with her cousin Shoshanna.

Hannah reveals her AIDS phobia when she realises Adam might not be practicing monogamy. Jessa avoids Marnie's meticulously planned day at a women's health clinic, where Shoshanna confesses a humiliating secret.

Hannah meets up with an old flame to find out how she contracted HPV, uncovering much more in the process. Marnie's boss introduces her to a cocky artist who piques her interest, while Jessa gets a baby-sitting gig.

Adam sends Hannah a "sext" message that puts her in a tailspin. Meanwhile, Hannah's boss gets touchy at her office job, Shoshanna reunites with a boy from camp and Jessa gets distracted while watching her charges.

Hannah decides to better her story by propositioning her boss but later retreats to Adam who has a different idea about their relationship. Marnie & Charlie assess their relationship & Jessa is out to reconquer an ex.

Hannah's parents fly her back home to celebrate their wedding anniversary. Though they hope she'll go on their date, she gets one of her own instead, and catches up with high-school friends who are mourning a tragedy.