Überraschend taucht Melanie bei Pacey auf. Ihr Onkel bietet ihm die Möglichkeit, an einem Segeltörn zu den griechischen Inseln teilzunehmen. Anders als vermutet, zeigt Danny Verständnis, als Pacey deswegen kündigt. Nach einer heißen Liebesnacht mit Melanie überdenkt Pacey seine Pläne noch einmal. Kaum dass Dawson und Jen unter einen Dach wohnen, gibt es erste Unstimmigkeiten. Kleine Alltagsprobleme und Jens Erfolg beim Radio trüben das Liebesglück der beiden.
Dawson and Jen realize that living together is not as much fun as they hoped to be. Between ruined toothbrushes and bathroom overcrowding, they're getting on each other's nerves. Jen faces a new challenge at work after she turns her regular show into an advice show. She mainly gives advice to other girls with problems, and makes statements on men that hurt Dawson's feelings. She comes home expecting a fight, but Dawson surprises her saying he won't fight or lie or cheat on her. Meanwhile, Melanie (Pacey's summer flame) shows up offering Pacey a job working with her uncle's new boat around the Greek Islands. After a lot of thinking, Pacey decides not to go, since he has developed a successful life in Boston working at the Civilization. Jack moves into the fraternity house and gets his own room, but has some problems staying there after he discovers he was supposed to be rooming with another guy who felt uncomfortable living with a gay guy. And Joey decides to give Elliott Sawyer another
Pacey reçoit la proposition de retourner en mer. Il hésite.
Jack est effondré: son premier jour au sein de la confrérie ne se passe pas comme prévu.
Les relations entre Jennifer et Dawson sont tendues...
Mentre Pacey si trova a scegliere tra una passione nuova e una vecchia, Dawson e Jen cercano di trovare un equilibrio all'interno della loro storia.
Jen e Dawson tentam se ajustar a sua nova vida, já que agora estão morando juntos na casa da avó dela. Além disso, o relacionamento dos dois fica estranho quando eles discutem sua vida sexual no rádio, onde Jen reencontra Charlie. Pacey descobre que talvez ele possa ir velejar nas ilhas gregas e fica dividido entre a viagem e sua nova vida em Boston. Jack decide se mudar para a fraternidade, onde descobre que um de seus amigos não quer dividir o quarto com ele.
Mientras Pacey debe elegir entre una nueva y una antigua pasión, Dawson y Jen intentan hallar el equilibrio en su nueva relación.