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.
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 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.
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.
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