After visiting her aspirational long-distance boyfriend in Italy, writer Arabella returns to London, where she is greeted by a deluge of frantic messages from her literary agents. With a matter of hours left to finish a draft of her second book, she plans to pull an all-nighter - but is soon tempted to join a friend on a night out.

Lunch with Terry gets Arabella thinking about the hazy events of the previous night, prompting her to probe Simon for answers. Growing increasingly desperate to put together the pieces, Arabella drops by Simon's apartment – and, later, finds herself at an unwelcoming doorstep. Meanwhile, Terry has a lousy audition, and a concerned Kwame rushes to Arabella's side.

Three months earlier, Terry visits Arabella in Ostia, Italy, where she's living large on her agents' dime. After procuring party favors, Arabella and Terry each have a wild night of their own.

Back in London and two months after the incident, Arabella meets with a therapist who encourages her to find relaxing and creative ways to cope with her trauma. Still anticipating the first draft of Arabella's book, her agents assign another client, Zain, to help her with the writing process. Kwame introduces his modest new love interest, Damon, to a stranger he met online.