#401 - Coming Home
 Joey and Pacey return from a blissful and romantic summer traveling the east coast aboard Pacey's boat, the "True Love." Now they have to face their senior year at Capeside High and before classes begin, they must confront their friends and the one question that's on everyone's minds…Did they or didn't they? Regardless, a lot has changed and the lovers wonder if Capeside was better off without them. Dawson has every intention of avoiding the happy couple forever, but Jen orchestrates an encounter between them at an end of summer party. While struggling with the fact that her boyfriend, Henry, has suddenly been sent away to school, Jen helps Dawson realize that he must confront his feelings and his friends' relationship sooner or later. While all may not be forgiven, the bond between Dawson and Joey has not yet been forgotten.
Meanwhile, Pacey's life is shaken up when his sister, Gretchen (Sasha Alexander), returns to Capeside and Andie gets a lesson in authentic French kissing from an exchange student (Jason Daniel Roberts, "The Real World's" Danny). 
#402 - Failing Down
 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.
However , a fresh breeze blows into town in the form of Gretchen Witter. 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.
#403 - Two Gentlemen of Capeside
 The winds of change are blowing through Capeside as a violent storm threatens lives and forces an unlikely hero to come forward. While the Farmer's Almanac may have predicted foul weather, skies are clear and it seems like a beautiful school day. When Dawson and Joey get excited over a current reading assignment, "The Two Gentlemen of Verona," a story similar to their own, Drue suggests that the two prepare a debate about the merits of the play. However, Drue's plan backfires and he too gets stuck working on the assignment with Dawson and Joey at the Yacht Club. Unfortunately, this means Joey can not take a celebratory sail with Pacey to mark his first "A" of the school year. Instead, Jen decides to voyage out with Pacey in an effort to lift her spirits. However, their jaunt turns disastrous when a violent storm with hurricane force winds tempts the fate of the "True Love" and the safety of those aboard.
Dawson Leery finds himself in the ironic position of having the best chance to rescue castaways, as only he might be able to predict what Pacey's next move will be. Meanwhile, Andie's emotional problems come back to haunt her during a college interview with Mrs. Valentine, an alum from one of her back-up schools. But while Mrs. Valentine may doubt her abilities, there is no doubt that she's the best person to have around during a crisis situation.
#404 - Future Tense
 The pressure is on as Capeside's class of 2001 faces the college application process and battles the "senior slump." Andie's applications are signed, sealed, and delivered in hope for early acceptance into Harvard, while Jack looks forward to the football season. However, an accident during practice lands him in a sling making him a permanent bench warmer - and his sister's constant nagging about the future does not help his pain. In a twisted attempt to gain popularity, Drue throws his old friend Jen a "retroactive" birthday party. As Jen well knows, while a lot has changed a "birthday" present from Drue proves that he's still bad news.
Meanwhile, Joey's in a crisis over the discovery that she's ranked fourth is her class. Panicked that her hard work won't pay off and that her goals may be out of reach, she takes consolation in a few too many drinks at Drue's party, forcing Pacey to take charge. And, Gretchen Witter becomes the newest bartender at Leery's fresh fish, which may give confused Dawson a good confidant.
#405 - A Family Way
 Gale sees no relief in sight from her bout with the flu until a pregnancy test reveals her true condition. Dawson is less than trilled that the Leery family may be adding another member, until he learns that his parents are planning to terminate the pregnancy. Feeling hurt and confused, Dawson confides in Gretchen who seems particularly uncomfortable with this topic. Finally Gretchen reveals her reason for returning to Capeside--she too got pregnant while at school and had a miscarriage. Not wanting to face similar issues and fearing that she may no longer be able to fend off Pacey, Joey decides to visit a free clinic to become more sexually responsible. Unfortunately, Bessie jumps to the wrong conclusion when she stumbles upon Joey's birth control stash.
Meanwhile, Andie convinces Jack to become a pee-wee soccer coach in order to augment his extra-curricular activities. However, the plan backfires when the advances of a player's older sister force Jack to reveal his sexual identity and bigotry resurfaces.
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