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After learning Gabi has a new boyfriend, Elena worries about maintaining her role in the family. Bobby meets his match on the tennis court, and Sam helps Gabi deal with the loss of her favorite sandwich when it's abruptly taken off the lunch menu.
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.
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