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.
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 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.
