#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.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.
#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.
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