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Hannah contacts her college boyfriend to find out how she contracted an STD, but learns perhaps even more shocking news from him. Meanwhile, Marnie is smitten with a pretentious artist at a gallery opening; and Jessa lands a babysitting job.
An appointment at a women's clinic doesn't go according to Marnie's detailed plans, mostly because Jessa will find any reason not to show up. Meanwhile, Hannah is preoccupied by an STD scare; and Shoshanna makes a startling revelation.
Adam's risqué text message sends Hannah over the edge; Jessa gets distracted while babysitting; Shoshanna reunites with a guy she knew at camp; Ray and Charlie stick their noses where they don't belong.