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Pacey and Jen ultimately call quits on the friends-with-benefits situation before anything happens.Henry and Jen's relationship is the main focus of her storylines, as well as her increasingly loving relationship with Grams, and the new experiences that Jen have with Henry, who provides her the kindness, respect and love that she had thus far never had, and been afraid to experience.Her heart isn't in it and Jen occasionally re-circulates with Dawson, Joey and Pacey, as well as befriending Jack Mc Phee.Jen also eventually finds a connection with his sister, Andie.After realising Joey's feelings for Dawson, Jen abates but also learns that Joey actually likes her.Faced with her ex-boyfriend from New York suddenly appearing in Capeside, Jen's memories of her life with her parents come flooding back and she breaks up with Dawson and says goodbye to Billy for good.
Later, Jen falls back into her bad girl ways, befriending the school's bad girl Abby Morgan, attempting to steal Dawson from Joey, and getting drunk at parties.She meets Dawson, Pacey and Joey, but doesn't share the reason why she's in Capeside, instead putting up a sunny demeanor.Although her fear and bewilderedness at her life shows itself in her hesitation to date Dawson, whom she has quickly developed strong feelings for.After Pacey breaks up with Andie, he too, is destitute and while trapped on Witch Island with Joey and Dawson, the two proceed to make out, deciding to pursue a friends-with-benefits relationship.
Jen's mother, Helen, unexpectedly shows up at Grams' house for Thanksgiving dinner.
Jen becomes Head Cheerleader and Homecoming Queen, after a mock cheertryout intended to ridicule the institution.