Ben and Sarah choose to bring their physical relationship to a halt when Sarah begins dating a co-worker who she thinks might be boyfriend material. Elsewhere, Aaron takes his relationship with Riley more seriously than she does and shows up to meet her for what he believes to be a dinner date, but quickly realizes things aren't what they seem.

When Aaron becomes depressed over an ex-girlfriend getting engaged, Ben and Fitz decide to take him out for a night on the town, only to end up arguing over a girl. Meanwhile, Sarah tries to befriend Riley and her wild lifestyle by hesitantly attending a party that makes her question her conservative ways.

Ben runs into an ex and reaps the benefits of her short-term memory loss. Meanwhile, Fitz fears his lesbian mother is lonely and tries to find her a girlfriend, but is surprised to find that she is already in a relationship. Elsewhere, Riley dates a man with a breast-feeding fetish.

Sarah struggles to get off the "Booty Call Track" and onto the "Relationship Track" with paramedic Evan, while Ben works toward the opposite with a girl he met over the weekend. Back at the loft, Fitz, humiliated by Aaron's extravagant gift on their "Roommate-aversary," tries to take Aaron on a fun, low-cost night out.

Aaron learns a girl he mentored in junior high has become a porn star; a doctor bribes Sara for help impressing Riley; Fitz and Ben visit a friend at the hospital.

Ben asks Aaron to invest in a new business venture; Sarah encounters some obstacles while dating a cute journalist; Riley tries to help Fitz become Chicago's number one bachelor.

Ben and Sarah go on their first double date together with another set of friends who show fluctuating interest in them. Elsewhere, Riley's new boyfriend introduces the concept of "full disclosure,” and a reluctant Aaron mediates a "truth off" between Riley and Fitz to see who is better at handling brutal honesty.