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. The decision-making process forces Annie, with help from her best friend Fran, to figure out who she is and what she wants from her life.
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. Things are looking up, until an internet troll appears and tries to drag her self-esteem back down where it started.
Annie isn’t going to let her troll ruin all the success she’s had recently. So, she invites Ryan to a work event, excited to introduce her boyfriend into her life.
Annie and Fran attend the Fat Babe Pool Party. Annie is so empowered by the experience and so furious with her boss, Gabe, that she 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. She is forced to confront her boyfriend, her boss, her roommate, and even her troll.
Annie and Ryan escape the potential wrath of the Troll and go camping. But reality comes crashing down when Annie finds out her dad is alone and her mom skipped town to Vancouver.
Annie starts her freelance career by interviewing the Troll. Fran is heartbroken after she finds out Vic is not exclusive. When no one reads Annie's article, she realizes going freelance may not be as positive a move as she thought when she quit The Thorn.
After a month of being her own boss, Annie is starting to crack. She can't find work and she misses her old friends from The Thorn. Ryan comes with her to Ruthie's roller-skating birthday party to reconnect with her old friends and face Gabe.
Annie comes back to The Thorn. She's lost her footing there and now is relegated to the Freak of the Week column. But she's in a great place with Ryan and takes him to dinner with her parents. The newly single Fran takes herself out on a solo date.
Annie goes with Fran to her cousin's traditional Nigerian wedding. Fran reconnects with her parents and has to deal with their old issues. Annie reconnects with Fran's brother Lamar and is forced to question whether Ryan is really a good match for her.
Gabe finally gives Annie a meaty article to write – about a women in business convention. Initially impressed, Annie realizes that it's really a way to monetize feminism. Gabe guides her to the conclusion that society just wants to put women in boxes.
Annie receives an invite to Gabe's monthly salon. There she meets the publisher of The Thorn who is impressed with her work. Annie sees that she has been selling herself short in her work life and her love life and maybe needs to push herself further.
Annie finally deals with the parts of her life that still challenge her—Ryan and her mom. Fran realizes she doesn't need to be dependent on relationships, she just needs to celebrate herself.
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.
