A newly single Annie jumps back into the dating world with mixed results, and Fran and Emily take their relationship to the next level.

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, and Annie, Fran, Ruthie, and Maureen have a girls' night out to help Annie get her mind off Nick.

For her first big piece, Annie visits a separatist community outside of Portland. Plus, Fran and Emily make a sex tape, and 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, and Gabe forces Annie to promote his new memoir. Plus, Annie reconnects with someone, and Fran 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 puts a relationship in jeopardy, and Fran and Emily have a serious fight.

Reality comes crashing down during Annie and Ryan's camping trip.

Annie interviews her troll, Fran is heartbroken about Vic, and Annie learns that going freelance might not have been the best move.

After a month of being her own boss, Annie is starting to crack. Ryan joins her at a roller-skating party to reconnect with her old friends.

Annie returns to The Thorn but has been relegated to the Freak of The Week Column. Meanwhile, she takes Ryan to dinner with her parents.

Annie goes with Fran to her cousin's traditional Nigerian wedding. Annie reconnects with Fran's brother Lamar and is forced to question whether Ryan is really a good match for her.

Gabe gives Annie a meaty article to write about a women in business convention. Though Annie thinks it's a way to monetize feminism, Gabe guides her to a conclusion about society.

Annie meets the publisher of The Thorn and the interaction makes her realize that she's been selling herself short in her personal and professional life.

Annie finally deals with the parts of her life that still challenge her Ryan and her mom. Fran realizes that she doesn't need to depend on relationships.

When the morning after pill fails and aspiring journalist Annie winds up pregnant, she weighs the pros and cons of having a child with her hook-up buddy.

Annie's writing her first article, going on her first date with Ryan and, finally, asking more from the people in her life than she has before.

Annie isn't going to let a troll ruin all her recent success. She invites Ryan to a work event to introduce her boyfriend into her life.

Annie posts a body positive article to the paper's website that explains exactly what it's like to be a fat woman in today's world.

While Annie deals with the fallout from her "Hello, I'm Fat" article with Gabe and her troll, Ryan guides Bonkers through an accidental mushroom trip.

Annie's been putting herself out there more than ever and her life is becoming a tornado of both good and bad.