Bailey goes to a wedding with Holly and all her relatives think they're married. Julia's new editor hasn't answered her about her book, so she tries to find her and not just sit and wait. When she finds her, she tells Julia that another book with the same story of hers has been published, so her book won't be published anymore. Thurber, the family dog, is sick. Claudia takes him to the veterinary. Charlie and Kirsten are in a double date with Daphne. Charlie quits his job after his boss says no to his projects, but when they talk, he gets back. Bailey and Claudia decide to put Thurber to sleep, and the whole family spread his ashes in the park, saying goodbye for the last time to the long-time friend.

When Bailey returns to Holly, her sister Fiona visits her and Bailey spend time with her to find out just what he wants to do with his life. Charlie seeks help from Bailey, because he has too much work. Bailey agrees later. Julia tries to get away from her writer's block by having sex with Adam. Claudia and Todd come closer.

A rival company is closing down, so Charlie and Bailey decide to take their clients. Suddenly, Mitch has a heart attack and Charlie decides to slow down the production line. One of the new clients offers Bailey a chance to get back to Business school. Mitch tells Charlie not to give up what they've worked so hard to built. He dies and Charlie thinks that it would be better to keep it a small company, so he can have more time for his family. Charlie asks Bailey to join him in the company. Julia has to decide what to do with her life. She is offered to be a speaker in a women conference, but turns down to get a new job as a columnist in a women magazine, where she has to write about futile things. Justin opens her eyes on what she is missing, and she decides that she should go to the conference. Bailey keeps pressuring Will and they have a fight. Holly decides to annul the wedding and move back to England, and Will decides to move back to college. Claudia is accepted for both Stanford an