James is Ryan's old college buddy. After graduating, the two both went to work for Ryan's dad, Henry but when Ryan quit, James went back on their plan and stayed at the company.
James first appears in Avoidance when he notices Kristen and Ryan are having lunch together. He tries to strike a conversation with his old friend but Ryan is uncomfortable and unwilling to participate. Kristen on the other hand is eager for human interaction and tries desperately to befriend him. Before leaving, James invites Ryan to go for a beer with him later on.
Wilfred asks who James is and Ryan informs him that he and James were best friends in college and worked at his father's firm together. Ryan and James both hated working under Henry and planned to quit and start their own firm but when Ryan left, James changed his mind. Ryan refused to talk to him since.
Ryan is at first planning on standing him up but after Wilfred ejaculates on him, a distressed Ryan decides to go. At the bar, James continues to make inside jokes with Ryan as an attempt to rekindle their relationship.
Ryan and James meet a final time in the episode and James admits that he was blackmailed into staying at the company. Henry told him that if he left, he would smear James' reputation so that he would never experience a successful career again. Now that the two are back on good terms, James warns Ryan to beware about the lengths Henry is willing to go to in order to get his son back.
James appears once more in Secrets at Jenna and Drew's wedding to tell Ryan that all the evidence in the case of finding out who sold secrets from Ryan's company to a rival one points towards Ryan. He says that Ryan's dad wants to help clear his name by becoming his lawyer. Their interaction is interrupted when Kristen comes over and hands James her baby before running away.