#100 -- Pilot
Best friends Dawson and Joey have been spending the night together since they were little kids in the quiet town of Capeside, but at 15, this ritual takes on complicated elements that change and intrude into their comfortable relationship. Though Dawson pretends to think about nothing but filmmaking, Joey knows that sexuality is bound to hit him over the head soon, and to her dismay, it does so with force when the blonde and lovely Jen appears next door visiting from New York. Meanwhile, their friend Pacey, who is rather a social outcast, decides to exercise his budding hormones by conducting an improbable flirtation with an older woman who turns out to be his English teacher. The only sexually satisfied people seem to be Dawson's parents, who still vigorously lust for each other, but behind whose passion may lurk an ugly secret.

#101 -- "Dance"
As Dawson struggles to complete his film by the festival deadline, he decides to mix business with pleasure by casting Jen, with whom he now has a budding romance. This continues to irritate Joey, for reasons she won't truly admit, even to herself. Dawson soon finds he has some competition in Cliff, an upperclassman who's not as "enlightened," but is handsome and popular for his football prowess, and is stunned when Jen accepts Cliff's invitation to the dance. Although not one to attend dances himself, Dawson now feels compelled to rush in and make an utter fool of himself. Pacey, meanwhile, moves forward with increasing confidence in his secret quest for romance with his teacher.

#102 -- "Kiss"
Dawson struggles to create the perfect setting for his first kiss with Jen, and Joey argues that all the scheming and planning to make the moment ideal is proof that Dawson is living in a Hollywood dreamland. His weekend plans with Jen are foiled again, as he is enlisted to be the production assistant on a film project for the class that he's desperate to join, but Dawson finally gets his romantic moment with Jen, who realizes at the last minute that everything is just a little too contrived. Meanwhile, Joey meets and falls for a handsome and wealthy boarding school student, who is equally taken with her. Pretending to be someone she's not to impress him, Joey jeopardizes her chances with him. Meanwhile, Pacey continues to doggedly pursue Ms. Jacobs, who shows signs of cracking under the pressure.

#103 -- "Discovery"
Dawson is surprised to find scandalous footage of Ms. Jacobs and an unidentified man making love outdoors, after he accidentally leaves his camera on location, and running, overnight. Panicked, Pacey reveals to Dawson that the tryst is between he and Ms. Jacobs. Meanwhile, on the eve of Dawson's parents' 20th anniversary, Dawson discovers that his mother has been having an affair with her co-anchor and Joey has known about it. Hurt and confused, Dawson wants desperately to tell his father. To further confuse matters, Jen reveals that she had been leading life in the fast lane in New York, which is why her parents sent her away. Completely put off, Dawson doesn't know how to respond to the fact that Jen is not a virgin.

#104 -- Hurricane
As a hurricane approaches Capeside, emotions run as high as the winds. Worried that her son may be on to her, Gale has her worst fears confirmed and realizes that she now has no choice but to come clean to her husband. Accusations and mistrust don't stop there, however, as neighbors Grams and Jen come over to Dawson's house to weather out the storm and clash with Joey's pregnant sister Bessie and her fiance, Bodie. And Dawson, who is already at the end of his rope over his mother's infidelity, lashes out at Jen over his own disillusionment with the fact that she is not a virgin. Meanwhile, Pacey is annoyed when he ends up at Tamara's house not alone, but in the company of his brother Doug, the dutiful cop.

#105 -- "Baby"
The miracle of life surprises everyone, as Bessie and Bodie's baby decides to make an early entrance. Finding her very pregnant sister on the side of the road, a panicked Joey transports her to Dawson's house to wait for an ambulance. A bad traffic accident and limited resources delay the ambulance, and it becomes very clear that Bessie is going to give birth on Dawson's living room floor. Desperate, Joey enlists Jen's grandmother, a registered nurse who disapproves of the interracial couple's decision to have a baby, much less one out of wedlock, to help with the birthing. Meanwhile, Pacey's affair with Miss Jacobs is leaked to the high school rumor mill, with news of the scandal traveling all the way to the school board. In an uncharacteristically mature move, Pacey gallantly saves Miss Jacobs' job and reputation, only to be given a heart-breaking blow.

#106 -- "Detention"
Dawson, Pacey, Joey and Jen all wind up spending an 8-hour Saturday in detention at Capeside High under the supervision of Mrs. Tingle, the school librarian. Abby Morgan, a fellow trouble-maker, stirs the pot by initiating a telling game of truth or dare to break up the monotony of the day. Afraid that Jen isn't physically attracted to him, Dawson's insecurity causes him to fight with Pacey. Matters are only complicated by the drawn-out truth or dare kiss between his best friend and his girlfriend. Later, Jen airs her frustration about not being accepted in the small town and frankly questions Joey about the friction between the two of them. While coolly composed most of the time, Joey panics when her intense feelings for Dawson threaten to boil over after she is dared to kiss him.

#107 -- "Boyfriend"
Jen is caught off guard when her old boyfriend Billy from New York pays a visit to Capeside to try to rekindle the relationship that abruptly ended when she left the city. Jen ditches school to spend the day with Billy, sending Dawson into a mire of insecurity about their relationship. Clearly conflicted, she tells Billy it's over, but the underlying passion in a good-bye kiss convinces him otherwise. Meanwhile, Pacey presses Joey about her feelings for Dawson. While she continues to deny her attraction, her actions make her true feelings perfectly clear to everyone but Dawson.

#108 -- "Roadtrip"
Dawson is miserable after being dumped by Jen, and Billy convinces him to ditch school to go to a club in Providence with Billy, where they can have their pick of eligible college co-eds. When Pacey catches wind of the plan, he invites himself along. All the way to Providence, Pacey chides Dawson about being too much of a nice guy, and Dawson sets out to prove him wrong. Surprising even himself, Dawson successfully picks-up his dream girl of the evening at the club, but with his mind still on Jen, he stops short of a rebound affair. The evening ends with a confrontation between Billy and Dawson, who both still want Jen back. Meanwhile, Joey accepts a ride to school from Warren, a brash football player, who then spreads a rumor that they slept together. Jen convinces Joey to take revenge and comes up with a plan to put Warren in his place. But, when Joey pretends to be pregnant, the lie gets out of control.

#109 -- "The Scare"
Dawson orchestrates a few schemes carefully designed to scare the tar out of his friends on Friday the 13th, and a timely news story about an at-large serial killer only increases the fright factor. Dawson plans to conclude the ominous day with a spooky, adrenaline-laced seance. Meanwhile, Jen reluctantly agrees to a date with Cliff, who vainly turns to Dawson for advice on how to impress her. And, Pacey invites a sexy and unbalanced stranger, whose crazed boyfriend threatens to deliver real danger to Dawson's door. All converge on at the Leery house for some heart-pounding fun, but when the power goes out, the phone lines are cut and loud noises cannot be explained, all look to Dawson for reassurance, only to realize that the terror at hand may not be Dawson's doing.

#110 -- "Double Date"
Unable to accept his breakup with Jen, Dawson seeks solace and advice from Joey, who must continue to mask her own feelings. Pacey abets Dawson in coming up with a save-face way to becoming "friends" with Jen that proves to be more than a bit misguided. Acting nonchalant about Jen's upcoming date with Cliff, Dawson goes so far as to pretend that he has a date for the same evening, and then suggests they make it a foursome and Dawson has to come up with a date-fast. Dawson's date immediately suspects she's being used but Dawson is able to allay her fears-for a while. Once the foursome hit the local carnival, however, the ugly truth rears its head for all to see. Meanwhile, to their mutual displeasure, Pacey is forced to spend remedial marine biology time with Joey, but a their project wears on, Pacey's attitude toward his lab partner takes an unexpected turn.

#111 -- "Beauty Contest"
Capeside's annual Miss windjammer contest gets turned on its ear when it draws some unexpected contestants. Jen persuades Joey to enter in hopes of winning the $5,000 prize for her college tuition. After being demeaned by his father Pacey is determined to move out of the house and get his own place. In the hopes of winning rent money, and also to further irritate his family, Pacey too, decides to challenge the rules and be the first male ever to enter the competition. As Jen begins to regret breaking up with Dawson, he starts to see Joey in a new light, while Jen becomes increasingly jealous.

#112 -- "Decisions"
Joey is given the opportunity of a lifetime when she is chosen to represent the highschool for a year in France. Escaping Capeside has been her life's dream, but now that Dawson sees her in a more romantic light, she is terribly torn. Adding to the stress, it is Joey's turn to visit her father in prison for his birthday and she decides to confront him with all of her anger and hurt. When Pacey decides to clear the air with his brother, Doug, he learns that Doug's relationship with their father is not as perfect as he'd believed. Meanwhile, Jen and Grams are elated when Gramps comes out of his coma, but when his conditions worsens they find common ground in their anguish. When Jen then seeks comfort from Dawson, Joey is horrified to find them in what appears to be a compromising position.