Joey and Phoebe conspire to arrange awful dates for both Rachel and Ross, hoping that appreciation of their former relationship will cause them to reunite.

Catherine takes the point in the investigation of an escalating series of peeping tom incidents. The crew is racing to stop the attacker before his crimes become more serious assaults. Meanwhile, Sara reopens the dormant case of her friend, a district attorney. The DA is facing surgery to remove a bullet she got in an attack that killed her husband three years prior.

Jack suffers Karen's wrath when he is seduced into friendship with her manipulative British romantic rival, who has set up house with Karen's ex-husband. Meanwhile, Will and Grace try to re-connect their lagging friendship with a competitive night of board games with their friends.

After taking care of a wounded prostitute and bringing her case to the attention of social services, Chen confronts her past by telling Pratt about giving up her baby for adoption. Romano is furious after Anspaugh notifies him he's not allowed to take part in surgeries. Kerry is promoted in favor of Romano, due to Alderman Bright's aid. Susan has a blind date. And while Carter is out of town, Abby receives word that Eric's private plane is missing and she refuses to contact Maggie.

The team investigates the disappearance of a flight attendant who may have been having a relationship with one of the pilots. They soon discover her car with blood and a knotted stocking in it. Eventually the team is forced to use untraditional methods to find the truth behind her disappearance.