||Like A Virgin
||29 SEPTEMBER 1999
| Dawson returns from spending the summer in Philadelphia with his mother. Meanwhile, Joey, who has frozen Dawson out all summer, realizes she is still reeling from their break-up; Jen gets more than she bargained for when she takes on the fascist head cheerleader; Mitch accepts a new position as Capeside High's varsity football coach; and although Pacey tries to be brave, he has had a lonely summer without Andie.
||6 OCTOBER 1999
| Dawson is recruited by his dad and Principal Green to produce a film for the football pep rally, but the stars of the film end up being Dawson and his lady friend Eve, not the Capeside Minutemen. Meanwhile, Pacey has enlisted Joey for assistance in bringing Andie back to Capeside, but their long-awaited reunion doesn't go exactly as Pacey had intended; and Jack comes to an unexpected understanding with his father who has returned to Capeside to be with Jack and Andie.
||None Of The Above
||Davis & Schneider
||13 OCTOBER 1999
| Dawson is stunned when Eve presents him with a sneak peak at the PSAT test and everyone is tempted to cheat including Joey, whose scholarship is dependent on her SAT scores, and Andie, who is desperately fighting for acceptance to Harvard. But when the test is stolen, it's Pacey that Dawson accuses. Meanwhile, Jack is insistent that the football team is purposely beating him down because he is gay.
||20 OCTOBER 1999
| Father and son are at odds when Dawson moves forward with a news piece for his mom's Philadelphia station using Mitch's star player, Jack, as his subject matter even though Mitch is vehemently opposed. Meanwhile, Joey and Pacey find themselves in cahoots when they must pay the price for ditching class; Andie jumps to conclusions and panics about the reasons Principal Green wants to meet with her; and Jen goes to great lengths to remove herself as head cheerleader but is shocked at the end results.
||Fattore & Kapinos
||27 OCTOBER 1999
| Dawson plays detective when Eve's mysterious ways, including breaking and entering and stealing, cause him to wonder about her reasons for being in Capeside, but the secrets he uncovers may drastically change the lives of others close to him. Meanwhile, Joey's misgivings of Rob lead her to crash his date with Andie but her good will backfires on her; and Jack goes against Jen's wishes and sets up a rendezvous for Henry.
||Secrets & Lies
||Berlanti & Gansa
||10 NOVEMBER 1999
| Dawson is torn about telling Jen the scandalous secret he has about Eve and even more distressed when his mom unexpectedly returns from Philadelphia. Meanwhile, Andie accuses Joey of sabotaging her chance to reunite with Pacey; and Jen shocks the entire town with the entertainment she has hired for the Annual Homecoming Queen Gala and shocks the very shy Henry even more when she asks him to be her escort.
||Escape from Witch Island
||17 NOVEMBER 1999
| In a bone-chilling installment, Dawson recruits Joey, Pacey and Jen to be his guerilla crew on a documentary for history class about Witch Island, a local spot shrouded in mystery for its reputation for being haunted by witches. They are haunted by tall tales of witches and love lost that has Dawson and Joey questioning their own romance and Jen and Pacey considering a new kind of friendship. Back at school, Andie takes her job on the school disciplinary committee a little too seriously when she tries to take back the halls of Capeside.
||Guess Who's Coming to Dinner
||24 NOVEMBER 1999
| When Jen's mom unexpectedly arrives in Capeside on Thanksgiving morning, Dawson confronts her about her secret past, and makes a decision to help bridge the gap between the estranged mother and daughter. Meanwhile, Jen continues to pursue a new type of friendship with Pacey, and Mitch and Gale make known the future of the Leery family.
||Four to Tango
||1 DECEMBER 1999
| Dawson is suspicious of Pacey's awkward behavior and misconstrues his actions when he learns Pacey has been spending time with Joey. Meanwhile, after rethinking the offer, Pacey cannot move forward with his no-strings-attached relationship with Jen, and Andie urges Jack to meet a gay student from a neighboring town who contacted him via the internet after seeing Dawson's news story.
||First Encounters of the Close Kind
||15 DECEMBER 1999
| Dawson, Joey, Jack & Andie spend the weekend at a Boston university for an advanced look at college and Dawson's entry in a student film festival. Joey's weekend guide is not what she expected; Andie's pursuit for an advanced admissions interview, leads her to some inspirational advice from an unlikely source; and Jack takes a chance and explores the local gay community.
||Barefoot At Capefest
|12 JANUARY 2000
| Dawson experiences an identity crisis when Principal Green's daughter Nikki emerges as another aspiring young director, and Joey experiences her own crisis when Dawson won't open up to her about the pain of his parents' divorce. Meanwhile, Jack's first efforts to hit on another guy are rebuffed, Pacey and Andie uncomfortably find themselves sharing the same afterschool activity, and Jen realizes that she may have passed up the chance at something special with Henry.
||A Weekend In The Country
||17 JANUARY 2000
| Joey's friends and their families work together to make sure that the opening of Potter's Bed & Breakfast is a success and that she and Bessie don't lose everything they have after Pacey surprises them with a visit from a prestigious travel critic. Throughout the weekend, Jen admits her concerns to Grams about getting close to Henry; Jack considers moving back home after hearing Andie's loving plea; and Dawson tries to understand the connection between his parents even after their divorce.
||26 JANUARY 2000
| Dawson makes the radical move of dropping out of film class to spend some time re-evaluating his teenage years. Back at Potter's, Joey is torn between attending Pacey's opening night and her date with A.J. who has come to Capeside for the evening. At the play, Andie must take over as director when the faculty director takes ill; and Jen agrees to meet Henry, but she throws him another block by bringing Grams as her date.
||The Valentine's Day Massacre
||2 FEBRUARY 2000
| Joey questions Dawson's state of mind when he and Pacey decide to lead their friends to a secret location party hosted by a group infamous for their complete and utter debauchery. Back at home, Jack's ex-girlfriend arrives from Rhode Island nursing a broken heart but is unaware of Jack's coming out last year and Jen's first date with Henry is a Valentine's Day she won't soon forget.
||Crime and Punishment
||Fattore & Gansa
||9 FEBRUARY 2000
| Joey is chosen to be part of a group of students to paint a school mural, but when hers is defaced before the unveiling, Dawson offers words of encouragement while Pacey takes action and risks suspension when he goes in search of the culprit. Meanwhile, when Andie's PSAT scores rank among the best in the country, she gambles with everything she has worked for and comes clean to Principal Green about the previously stolen test; and Pacey moves in with Deputy Doug when their sister and her kids move back into the Witter house.
||To Green, With Love
|16 FEBRUARY 2000
| Joey relies on the support of Pacey and A.J. to rally the students in protest against the school superintendent after he forces Principal Green to resign for expelling the student who destroyed Joey's mural. Meanwhile, Dawson and Gale both go back to their respective places in back and in front of the camera to produce a piece about the ongoing school protest which ruffles more than a few feathers of the school board hierarchy.
||1 MARCH 2000
| When Joey turns to Pacey for rescuing after she flees Boston halfway through her visit with A.J., the two old friends may finally confront their growing feelings for each other. Meanwhile, to avoid suspension, Pacey becomes a mentor to a young boy and must contend with a little version of himself with a big attitude; and behind Gale's back, Dawson asks Mitch to help with the opening of her new restaurant.
||5 APRIL 2000
| Pacey hopes taking Dawson to their favorite childhood camping spot will help ease the pain when he tells Dawson about his new feelings for Joey. Meanwhile, Joey deals with the emotional fallout from her kiss with Pacey by spending girls' night out with Jen and Andie, but to Jen's surprise they stumble upon a birthday party for Henry that she wasn't invited to.
||26 APRIL 2000
| Dawson invites Joey, Andie and Pacey to spend Spring Break in the mountains at his aunt'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. Meanwhile, back in town, Jen becomes surprisingly territorial when another woman flirts with Henry.
||The Longest Day
||3 MAY 2000
| In a story that replays the same day's activities from three different perspectives, Joey and Pacey vacillate on the ways to tell Dawson about their feelings for each other. But when the truth does come out, Dawson's reaction is the one they hoped they wouldn't get. 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.
||Show Me Love
||Tigelaar & Henderson
||10 MAY 2000
| As Capeside prepares for the annual spring regatta, Dawson and Pacey compete for the winning trophy, only Joey is tired of feeling like the prize. Meanwhile, after many weeks of mixed messages, Gale makes the first move with Mitch, and after Jen finally forgives Henry for his one-track mind, he gives Jen the most romantic night of her life.
||17 MAY 2000
| Dawson, Joey and Andie prepare their own unique prom when they learn that the committee has scrutinized Jack's selected date. Dawson, who has invited Joey to be his date, uses the special evening to try to win her back and make Pacey jealous; Andie persuades Pacey to be her escort but her evening ends by consoling him about his love life; Jen becomes outraged with Henry when he reveals he is leaving Capeside for the summer.
|24 MAY 2000
| After an emotional day filled with love, tears and wedding vows, Joey ultimately much choose between her love for Dawson and her new feelings for Pacey. Across town, Grams talks about love and regret with Jen, while Jack and Andie make a decision to drive all night so that Jen can see Henry one last time.