Darryl Philbin - Seasons 8-9

Seasons 8-9

During "The Incentive", it is established that Darryl is dating his ex-wife Justine, although the relationship seems short-lived when she seems to take an interest in an employee of Darryl's in "Lotto". During which, the warehouse employees win big in the lottery and quit their jobs on the spot, prompting the sales staff to pick up the slack and try to get orders out on time. Darryl was originally part of the bet by using his own birthday as the lucky numbers before opting out when Jo promoted him to work in the office. Coupled with Justine's interest in someone else, a despondent Darryl self-sabotages his job when the branch desperately needs new warehouse staff. When he and Andy try conducting a group interview, it ends in disaster when he makes disparaging remarks to Andy's frustration. Darryl tries to get himself fired by Andy, before admitting that he wanted the branch manager job, as he believed it was his. However, Andy, who had asked about Darryl's potential to become branch manager before he accepted, is direct and tells Darryl that he gave up the ambition by not continuing with college courses (under Deangelo's brief management) and prioritizing his personal life over a potential career, as well as pointing out that Jo Bennett really liked Darryl and saw potential in him. Although Andy promises that he can help Darryl continue his education if he chooses, and the two reconcile. Darryl says in a talking head interview that lottery balls won't define his future, but two black balls and he hires a new warehouse crew. Darryl also plays along with Andy's new nicknames, referring to Erin as E-dog after she calls him D-Dog.

In "Garden Party", Andy hosts a garden party to impress both the CEO and secretly his parents. Darryl overhears a conversation via a baby monitor, where Andy is browbeaten by his father over his job status. He later confides to the camera that he understands why Andy tries to prove himself to everyone. When Andy tries to leave early as the garden party turns into a staff barbecue, Darryl prevents him from leaving by giving him food and in turn, cheering him up.

In Gettysburg and Trivia Darryl, along with Jim, supports Andy as he struggles with being manager. He appears to accept the fact that Andy was chosen over him.

Darryl seems to like the new warehouse worker, Val, in several episodes including Doomsday and Special Project. In After Hours, Val's boyfriend Brandon gets jealous of her and Darryl, to which Val claims there is nothing going on. Darryl, however, says a relationship between the two is not ridiculous after encouragement from Pam and Andy.

In Free Family Portrait Studio, Darryl let's former warehouse workers Calvin and Hide to come back to work after their investment in an energy drink for Asian homosexuals falls through. Darryl also let's Val and Brandon know that he is pursuing her, to which Brandon insults Darryl, who takes it in stride. Val, impressed with his bravado, holds his hand in a portrait with him and his daughter Jada.

In Roy's Wedding, it is implied that he and Val are together. In Andy's Ancestry, it is revealed that Andy gave him the title of Assistant Regional Manager and he is excited to find ways to increase productivity, but ultimately grows increasingly dissatisfied as Andy is too concerned about his personal issues to listen to his job suggestions. He tells Jim in the warehouse that he wants to quit. Jim tells Darryl about his sports marketing job opportunity in Philadelphia and offers him to join. Darryl then convinces Jim to tell Pam about the opportunity before proceeding. In "Dwight Christmas", Darryl suspects that Jim forgot about his offer to take him to his Philadelphia job, and as a result, gets extremely drunk and prepares to tell Jim off. Before he can, Jim reveals he talked to his friends about giving Darryl a job interview.