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.

Hannah tries a different tack with her boss to counter his inappropriate office behavior—she propositions him. Meanwhile, Marnie does some soul-searching about her relationship with Charlie; and Jessa wants the last word with an ex.