Reeling after a nasty run-in with Natalia at Ray's new coffee and pizza place, Hannah and a reluctant Adam host dinner at their apartment with Marnie, who is living at home in New Jersey and still raw from her breakup with Charlie, and Shoshanna, who is alternating nights of sexual freedom with academia after her breakup with Ray. Meanwhile, Jessa pushes buttons, and new friend Jasper illuminates her daddy issues.

When Caroline, Adam's eccentric and emotionally toxic sister, shows up unannounced, Hannah offers her a place to stay, despite Adam's protests. Marnie's control-freak tendencies reach full tilt at Hannah's 25th birthday party. Ray settles into his role as manager at the new restaurant, but has a harder time keeping cool around Shoshanna.