Many of Hannah's friends and acquaintances are at crossroads in their respective relationships. After their few sexual encounters, Marnie and Charlie will find out if they are indeed on the same page of what that sex actually means. Shoshanna isn't sure if she can handle Ray's negativity anymore - what he sees as his critical thinking - or if she can even tell him what she is feeling in the matter. Ray, on the other hand, takes indecisive action to be who he thinks he needs to be for Shoshanna. And after their one disastrous sexual encounter, Adam and Natalia get back on track with what Natalia is looking for in a boyfriend, but it may not be quite who Adam truly is as a person. Meanwhile, Hannah's life is spiraling downward out of control. David threatens to sue if she doesn't produce the pages for which she received her advance. She won't admit that her inability to write is not a cause of her ear issue, but rather that her ear issue and her inability to write is a manifestation of ...