#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.
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