Gail drops a bomb on Mitch and Dawson, saying that she might be pregnant, but she is conflicted whether or not to keep her baby. As a result, Dawson seeks solace with his growing hobby of photography and confiding in Gretchen about his troubles. Meanwhile, Joey seeks advice from Jen because she has the feeling sexual intimacy with Pacey is approaching. Jen tells her to go to the clinic as prevention. Bessie finds out and berates Joey about the risks of sex. Also, Jack and Andie are coaching a little league of soccer kids, and he soon lands in an awkward situation when a teammate's older sister starts to flirt with him. He feels pressured to tell her that he's gay, but he soon regrets it when most of the parents turn out to be homophobic.

A sailboat owned by Capeside High's pompous Principal Dave Peskin, with "Class of 2001" written on the sail, and with his pet dog aboard, is found in the school swimming pool as part of a major school prank. As a result, Mitch Leery and Principal Peskin are after the guys who did it in which Dawson, Pacey, Jack and Drue are main suspects. Since, the dog that was on the boat instantly recognized Jack, Pacey had access to the yacht club and Dawson had access to the school keys. Each one has alibis for that day; Jack was at the soccer field with Jen to help plan a game. Dawson was cleaning Mr. Brooks parlor where he discovers that the that the old man was a former filmmaker from the 1950's. Pacey was with Doug on a routine police patrol where they squabbled about Doug's well being. Drue, despite his denials, is revealed as the culprit. But at the end, Joey finds out that Dawson, Pacey and Jack all teamed up to pull it off and to get Drue into trouble.