Jen tries to work out why Henry seems distant and surprisingly gets some insight on the matter from Jack.
Reality never hits harder than when summer's over, and that time has come for the new senior class of Capeside High. As if going back to school and facing college admissions weren't bad enough, Pacey finds out that he took off on his summer sail before discovering that he failed three of his junior year classes. Jen not only has to deal with a long distance relationship, she gets dumped by Henry and worse yet, she gets the news from Jack. While she lashes out at the bearer of bad news, Pacey panics about his future and tries to hide his failure from Joey. Joey, meanwhile, is worried about how to pay for the ivy league college she hopes to get into, and gets busy wrangling a job at the town's tony yacht club.
A fresh breeze blows into town in the form of Gretchen Witter, however. Pacey's big sis seems to have a few problems she may be running away from, but this also appears to make her the perfect advisor for her brother and his confused friends. Not only does she set Pacey straight that if he thinks he's failed now, he'll have truly bottomed out if he doesn't level with Joey, but she brightens Dawson's day as well. As someone he used to have a crush on, she's now able to remind him a bit of the things that make his blood run a little quicker, stirring the torpor he's settled into.