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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.
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.
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.