In the opening scene, Chandler assists Joey in rehearsing for an audition that involves smoking a cigarette. Joey, a non-smoker, coughs after attempting to smoke, prompting Chandler, a former smoker, to demonstrate the “proper” technique. However, Chandler becomes addicted to smoking again after taking a few drags. Throughout the episode, the group attempts to persuade him to quit, which frustrates Chandler. He defends his smoking as a personal flaw and accuses the others of hypocrisy, pointing out their own irritating habits (such as Monica’s snorting, Joey’s knuckle-cracking, Phoebe chewing her hair, and Ross’s over-pronunciation).
Meanwhile, Phoebe discovers that her bank has mistakenly credited her account with an extra $500. Despite the group encouraging her to keep the money, Phoebe decides to return it. However, instead of taking back the money, the bank gives her an additional $500 and a football phone. Phoebe, unwilling to keep either the money or the phone, gives both to Lizzy, a homeless woman. In a twist of fate, Lizzy buys a soda for Phoebe, who discovers a severed thumb floating inside. The soda company compensates Phoebe with $7,000.
Monica is hesitant to introduce her new boyfriend, Alan, to the group, fearing they will ridicule him and drive him away as they have done with her previous dates. To her surprise, the group finds no fault with Alan and enjoys his company. Alan even convinces Chandler to quit smoking during a brief phone call, after the group’s failed attempts. However, Monica does not share the group’s enthusiasm for Alan and decides to end the relationship. Ironically, Alan confesses to Monica that he cannot stand the group. To spare their feelings, Monica keeps this revelation to herself.
Chandler attempts to quit smoking using patches but ultimately gives up and decides to buy cigarettes. Phoebe offers him the $7,000 she received in exchange for him not smoking again, to which Chandler agrees.