Marnie micromanages her upstate wedding to Desi; Shoshanna is tasked with carrying out Marnie's wishes; Fran has an awkward moment with Adam; a dejected Ray steps in to help Desi
Fran moves in with Hannah due to his unstable roommate; Jessa and Adam spend time together at the carnival; Hannah visits her dad; Elijah has a new love interest; Ray's coffee shop is losing customers.
Shoshanna finds her beloved new life in Japan threatened, Adam and Jessa's complicated friendship continues, and, upset at finding photos of his ex-girlfriends on his phone, Hannah sends nudes to Fran.
Hannah and Fran have an exaggerated argument and she is left feeling hesitant about their relationship, Desi makes another thoughtless decision without consulting Marnie, and sparks begin to fly between Jessa and Adam.
Hannah and her mother head to a retreat, with surprises in store for both, Abigail visits Shoshanna in Tokyo, and Jessa takes an important step in her relationship with Adam.
Hannah gets into trouble outside New York, Marnie meets an obstacle, Jessa and Adam are left holding Caroline's baby, while a dejected Shoshanna returns from Japan.
A newly inspired Hannah prepares for a writing event, Marnie asks Ray to go on tour with her, Shoshanna basks in her newfound success, and Jessa and Adam's relationship starts to crack.