Naomi has constant flashbacks to her rape and begins taking sleeping pills in order to sleep through the night. Mr. Cannon invites Silver over to his apartment to watch his new documentary and secretly slips something in her drink. Meanwhile, Teddy wakes up from a night of drinking and realizes he hooked up with someone. Dixon learns that, despite what he assumed, Ivy is a virgin. Annie confronts her boss, Katherine about her awkward behavior and is shocked when she makes her an offer she may not be able to refuse.