Dawson invites Joey, Andie, and Pacey to spend Spring Break in the mountains of Vermont at his Aunt Gwen's home. But the trip is filled with tension as Joey and Pacey continue to battle about their feelings for each other and Andie becomes intrigued with the gang's childhood friend, Will, who is visiting. Back in Capeside, Jen, working as the hostess at Gail's new restaurant, Leery's Fresh Fish, becomes surprisingly territorial when a waitress, named Shelley, flirts with Henry who's now working there as a busboy. Also, Gail and Mitch question their current situation over being partners in the restaurant.

In this unusual episode that replays the same day's activities from three different perspectives: after Pacey unveils his new sailboat, named 'True Love', he and Joey vacillate on the ways to tell Dawson about their feelings for each other. But each time they decide to tell Dawson about them being romantically involved, they chicken out. But when both Pacey and Joey get together and decide to tell Dawson about them, Dawson's angry reaction is what they hoped they wouldn't get: Dawson reveals that he already knows when Jen had earlier that day told him about Joey and Pacey after assuming that they told Dawson. Meanwhile, Andie, who thought she was over Pacey enough to date, accepts a date with Capeside visitor Will, but their first date is ruined when she also learns about Joey and Pacey now a couple. Pacey also leaves the trouble-making Buzz with his brother Doug for the entire day as Andie deals with her feelings for will, Also Jen deals with Henry who wants to take their relationship to the next level.

As Capeside prepares for the Annual Spring Regatta boat race, Dawson and Pacey compete with each other for the winning trophy, only Joey is tired of feeling like the prize. Meanwhile, after many weeks of mixed messages, Gail makes the first move with Mitch. After Jen finally forgives Henry for his one-track mind, he gives Jen the most romantic night of her life with a moonlight picnic atop a building overlooking the bay.