Joan is the subject of office gossip and jokes after she begins dating a younger man who works in the mail room. She is embarrassed by the attention, and winds up hurting Chris's feelings. William is upset when Chris usurps his spot as pitcher on the company softball team. Maya fears that the persistent Stan will expose their involvement to Darnell.

Joan engages in surprisingly risky behavior after she begins dating a younger man, Chris. However, her friends urge her to re-consider the relationship after she inadvertently takes ecstasy at a night club. Meanwhile, Toni hires William as her attorney and tries to monopolize all of his time with trivial matters.

Joan decides to waive her ""three-month"" rule and sleep with Chris, but then receives a phone call from Sean. When she learns that Sean is back in town, she dumps Chris and expects to reunite with Sean. However, he stuns her by revealing that he is engaged. William expresses an interest in Lynn's co-worker, only to find that she is a lesbian with a crush on Lynn. Maya considers telling Darnell about her affair with Stan, but her friends talk her out of it. He soon discovers the truth in an unexpected way.

Joan fears she has hit an all-time low after she holds a ""Bring Your Ex"" party, but doesn't get a single phone number. She eventually winds up swearing off men to train for a marathon. Maya still struggles to get Darnell to talk to her after a month apart. William threatens to throw Lynn out of his house unless she lands another job. Toni laments the lack of drama in her life.