Jack agrees to have a drink with Diane after a stressful workday. Phyllis and Damon are having dinner at Yves' when Damon begins to charm Phyllis as she starts to reveal Newman's business secrets. Just as she is about to spill, she spots Jack and Diane together. Phyllis is angry that Jack would turn her invitation to dinner down but later go out with Diane. At Kevin's apartment, Lily and Kevin get intimate as Kevin turns on the charm. A worried Neil tries to reach her on her cell phone but she doesn't answer. J.T plucks up his courage to ask Colleen to a concert but is crushed when Colleen's date, Eli, arrives. At the hideaway, J.T plays his guitar and sings but is surprised when Colleen enters.