Freelance photographer Trip (Tommy Dewey), Katie's secret boyfriend, returns from Syria. Carol, whose negativity Katie blames for previous breakups, discovers the relationship but likes Trip; Katie suspects Carol investigated him. Katie learns Trip is a wealthy heir, while Carol had learned his mother is deceased, enabling her to take over that role. Katie realizes her misgivings about Trip are her own, and she breaks up with him; he is disgusted by Katie and Carol's behavior, anyway. Chuck decides to prove his masculinity by field reporting from South Sudan, but Justin discovers Chuck is a coward, whose war zone footage is so embarrassing it drove his previous editor from the business. After Justin and Greg mock him, Chuck terrorizes them with firecrackers, exposing their own fears and purposefully earning a travel ban from HR.