A newly single Annie jumps back into the dating world with mixed results, and has a traumatic encounter at the doctor. Fran and Emily take their relationship to the next level. The Thorn faces serious cutbacks.

Amadi sets Annie up on a disastrous blind date. Fran is sick of working from home and takes a job at a salon. Bill and Vera make a big announcement about their future.

Annie demands more hard-hitting assignments at the Thorn's annual creative retreat. Fran has trouble making friends at her new job. Annie, Fran, Ruthie, and Maureen have a girls' night out to help Annie get her mind off Nick.

For her first big investigative piece, Annie visits a separatist community outside of Portland. But is she out of her depth? Fran and Emily make a sex tape. Annie tries to move things forward with Nick.

Annie faces backlash over her separatist article, and realizes she might deserve it. Fran introduces Emily to Nigerian food, and her mother.

Annie tries to make amends after a professional disaster, while Gabe forces her to write a profile of him to promote his memoir. Annie reconnects with someone she initially wrote off. Fran visits Emily's parents' house for dinner and learns a big secret.

Annie, Will, Fran, and Emily spend a weekend at the Oregon coast, and Annie and Fran reminisce about the early days of their friendship.

The Thorn staff hears rumors that the paper has been sold. Annie crosses a boundary of someone she cares about and puts their relationship in jeopardy, while Fran and Emily have a big fight. Fran and Annie lean on each other and wonder about their future.