After Dawson, Joey, Jen and Pacey individually commit various violations at school, they all get stuck together for an eight-hour Saturday of detention, along with Abby Morgan, a trouble-making imp, where tensions still run high between all of them when Dawson and Pacey turn against each other, and Joey offers a tearful, partial explanation for her personal anger towards Jen.

Hoping to get over his breakup with Jen, Dawson and Pacey join Billy in a boys night out to Providence. Meanwhile, Jen handles damage control after Joey becomes the subject of a rumor at school when a jock tells everyone that he and Joey are physically involved.

Dawson gets in trouble with Joey when he reads an entry in her diary about her true feelings about his fantasy life of filmmaking. Meanwhile, Dawson is so self-involved with repairing his love life that he forgets Pacey's 16th birthday. As a result, Pacey, who also failed his drivers' ed test, decides to throw himself a pier party bash with a little help from Andie. Jack McPhee, Andie's older brother, gets a job at the Ice House restaurant which Bessie runs. Meanwhile, Abby Morgan begins to become a negative influence over the lonely Jen by taking her out carousing for guys and drinking. Also, Gayle confides in Grams, and Mitch with a friend, about their troubled marriage.

An economics class project pairs Dawson and Jen as husband and wife, as well as Pacey and Andie as a married couple. Jen, with a little of Abby's help, tries to take advantage of this project to get closer to Dawson, while Pacey gets to know a little more about Andie's background from Jack. While doing this project, Joey learns that as a single parent, she has a better chance of success in life, but does not see the same for Bessie who begins pressuring her to work harder at the Ice House. Also, Mitch and Gale's marriage continues to deteriorate to a point where neither one wants to be around the other.

Tamara Jacobs, the former Capeside High English teacher who left town to avoid a scandal after her affair with Pacey was almost exposed, shares an awkward reunion with him as she's temporarily back as a real estate agent, who is trying to sell Mitch a warehouse which he hopes to open his own restaurant. The encounters triggers old emotions in Pacey and curiosity in Andie who asks Dawson for advice on Pacey's likes and dislikes. Meanwhile, Joey finds a new joy in art and takes the time visiting a gallery with Jack who shares her newfound love, but Dawson does not have the same interests. Also, Abby tries to get Jen to help her flirt with an attractive seaman, named Vincent, who rejects Abby's over-played advances, but accepts Jen's more softer approach.

Emotions run high during the monthly night of the full moon when parental problems cast a pall over Dawson and Joey's new romance as Dawson finds himself stuck in the middle of Gail and Mitch's hostile feud over people they invite over; he with Miss Jacobs over the property and she with a new co-worker. Meanwhile, Pacey is troubled when he tries to meet Andie's elusive parents, and sees first-hand the home life that Andie avoids which involves her delusional mother unable to let go of Andie and Jack's older brother whom died the previous year. The rife between Jen and Abby increases as Jen invites Vincent over to her house for a date. Left alone to run the Ice House, Joey and Jack share a 'tender moment' during a power outage.

Dawson is rocked by two setbacks in his life. First he learns that Mitch and Gail have decided to separate. Then later at Capside's formal Homecoming dance, he learns about the kiss between Joey and Jack, setting off a chain of fireworks and events that shatter his lifelong friendship and newfound romance with Joey. At the same time, the night gives Jen a chance to use Joey's mistakes to try to get back together with Dawson, but it doesn't work. Also, Pacey tries to be honest with Andie, but ends up breaking her heart when he flirts with cheerleader Christy Livingstone.

Andie decides to run for student body president and asks a reluctant Joey as her running mate. But Andie's run lands her on a campaign trail of tears when the devious Abby learns and begins advertising her dysfunctional family situation. Meanwhile, Jen helps Dawson take steps to deal with his powerlessness over his parent's divorce by taking him out on a delinquent spree of pranks as well as a moonlight swim in the nude. Also, Jack shuts out Joey for he does not want to talk about his family problems with her or anyone.

A series of 'horrifically epic' tryouts for his latest movie project, now involving a teen romance, prompt a steamy dialog between the two stars Chris and Abby, while director Dawson and producer Jen decide that they may have to recast Abby's role. Meanwhile, Jack poses in the nude for Joey for her art class' project sketch, who feels herself drawn towards intimacy. Also, Pacey sets out to fulfill Andie's dream date on his own with a romantic dinner, and a encounter in a hotel room.

Abby and Chris find an anonymous love note at school and set out to find who wrote it. Abby figures out that the author and intended recipient apparently had sex the night before and, in her true devious fashion, she sets out to expose the affair. The three suspect couples are: Dawson and Jen; Joey and Jack; Andie and Pacey. Abby and Chris work from clues about Joey's night of sketching after discovering her drawings of a nude Jack, while angry Dawson sets out to find Joey and Jack, while Pacey becomes distant towards Andie after their romantic dinner. In a true Gothic themed mystery novel backdrop complete with a thunderstorm and lighting, Abby and Chris gather all six suspects into a classroom after hours to bring out the author and which couple, if any, went "all the way".

The gang explore uncharted waters when the girls, Jen, Joey, Andie and Abby spend a day with Gail doing a TV report on teenage behavior amid the tensions between all of them over Jen and Joey's continuing feud and Abby's continuing insensitivity. Meanwhile, Dawson and Pacey explore their own uncharted waters when they go on a father-son fishing trip with Mitch and Pacey's grumpy and critical father, Sheriff John Witter, as well as Jack whom Pacey invites to tag along which brings out more tension between Dawson and Jack.

On Dawson's 16th birthday, he, Pacey and Andie follow her therapist's advice and throw themselves into an unabashed night of recklessness where both Dawson and Andie get drunk at the jazz club and end up on stage singing the blues. Meanwhile at the Leery house, Joey is organizing a surprise party for Dawson. But the longer the guest of honor is a no-show, the more she is subject to surprises of her own. Abby and two of her girlfriends crash the party and taunt Jack over his recent 'coming-out.' Jen and Ty finally face up to their potentially irreconcilable differences in which they break up for good. Also, Gayle and Mitch come to decisions about how to raise their son in light of their divorce.

Dawson's confidence as a filmmaker is shaken when his new film class teacher, Nicole Kennedy, a Hollywood movie studio executive on sabbatical in Capeside, speaks her mind and tells him the painful truth about his new romance movie and its faults. Meanwhile, the future is unsure for Joey when she visits a Gypsy fortuneteller at the annual Capeside Fair, who advises her to be open to every new opportunity that crosses her path. Shortly after, Joey stumbles into Colin Manchester, a gorgeous photographer who brings out Joey's free-spirited side during a wild photo shoot. Also, Jen tries to persuade Grams to go out with an old flame, and Pacey becomes more uncertain about where he stands with Andie.

With Joey's father back in town after being paroled from prison, he persuades Bessie to expand the Ice House to cater weddings. Needing help, they enlist the services of the gang as staff. Andie tells Pacey that she hates weddings, but he loves them, while Joey doesn't think her ex-con father should be seen around Capside. In a comedy of errors, Jack and Dawson battle to help a scared bride, Andie and Pacey scramble to fix the wedding cake, while Mitch shows up with his new girlfriend Nicole Kennedy making Gayle sad, and Dawson angry. Also, the trouble-making Jen and Abby crash the ceremony to steal some food and liquor for another night out which eventually leads to tragedy.

In the aftermath of Abby's death, all of Capeside is attempting to 'whitewash' her life. But all the hypocrisy is making Jen angry knowing that Abby's 'good life' was all a scam. At Abby's funeral, Jen delivers part of the eulogy where she embarrasses Grams by announcing that Abby taught her the falseness of God. Meanwhile, Abby's clueless mother asks Andie to deliver the eulogy after mistakenly thinking that they were friends. Joey is afraid to attend the funeral which brings back bad memories of her own mother's funeral while Dawson persuades her to overcome her fears. Also, Gail tells Dawson that she has accepted a job offer as an TV executive in Philadelphia.