The season begins with Ross and Rachel now happily dating with a variety of fun, inconsequential stories, like Rachel’s Princess Leia role play and Ross and Rachel attempting to give Chandler boyfriend lessons. Rachel, encouraged by Joey (Matt LeBlanc) and Chandler to quit waitressing, leaves her job to pursue a career in fashion. When venting her job woes to Monica, a customer named Mark mentions a vacancy in his department at Bloomingdale’s that, eventually, Rachel gets. Ross becomes jealous and paranoid, believing her new boss has amorous intentions.
When Rachel’s forced to work on their first anniversary, Ross arrives at her workplace with a picnic basket and generally barges in, gets in the way, and makes a mess of the situation. They argue and Rachel suggests that they take a break.
After their fight, Mark comes over to Rachel’s apartment in a gesture of platonic comfort. During a phone call, Ross hears Mark’s voice in the background and becomes convinced his suspicions are true. He hangs up and, depressed and drunk, has sex in a woman he meets, Chloe. He later listens to a voicemail from Rachel in which she explains that she doesn’t want a break after all and wants to be in a relationship with him. Ross tries to hide his drunken error, but fails miserably.
Rachel splits with him after learning the truth. Their relationship really falters, argument after argument, until they agree to a mutual détente: They’ll be civil for the sake of the group dynamic. Ross begins to date a woman named Bonnie who Phoebe knows—that is, until he learns that Rachel still has feelings for him. He must decide between Bonnie and Rachel while the friends are at the beach house.