In November 2015, Jim Kittsworth was at Whitefeather & Associates working a case while listening to music and drumming along with his fingers. He was interrupted by the head paralegal Paula Proctor who complained that he was being to loud. Tim told her it needed to be that way because if he couldn't hear the base his rhythm would be off. Jim then shot Paula with a nerf dart from his toy gun which made Tim laugh. He gave Tim a high five when he apologized to Paula but called her by the name 'Pamela' so he could take it back. When Tim continued the joke by calling Paula that name too he fist bumped with Jim over their sophomoric antics. He came to regret his he treated Paula when Darryl put her in charge of the office.
First she had him and everyone else at the firm give up thier cell phones. When Tim was in the break room drumming a beat on the table Paula repeatedly hit his hands with folders. After Darryl returned to the office, Rebecca complimented Paula on how she got the office working efficiently. Tim chimed in and started teasing Paula again by calling her Pamela once more. He looked to Jim for a fist bump but instead his friend surprisingly defended Paula, Tim reprimanded Jim for calling her the wrong name and Tim awkwardly backed off. Together Paula and Jim started making fun of him and had a laugh at Tim's expense. Paula then told Jim to wash her car and Tim walked off confused by what he witnessed ("Josh and I Are Good People!").
Sometime later, Tim and the rest of the staff were called to a meeting in the boardroom by Darryl. He had an announcement to make and asked Tim to give him an improvised drumroll as a lead in. Tim did as he was asked and Darryl told his employees that he was coming out as a bi-sexual (♫ Gettin' Bi ♫). Tim and his co-workers were unfazed by the announcement and he asked his boss if he wasn't just gay. He then stole the spotlight away from Darryl by pointing out an article he on his tablet about Rebecca. She had gotten national attention due to her recent court case against Greater City Water and become something of a celebrity. Afterwards, Jim went to Rebecca's office to let her know the mayor of West Covina was there to see her ("Josh is Going to Hawaii!").
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