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She starts seeing a therapist to speak about all her issues from her past, which culminates in a visit to her father.We learn during this visit about the incident that escalated her wild behavior - when she caught her dad cheating on her mother and sleeping with a teenage girl.Jen moves in with the Leerys and phones her parents to see if she can return to New York, to no avail.Luckily, Jack is there to support Jen in this trying time and eventually Jen approaches Grams about starting over – with Jack in tow.

Life in Capeside this way proves lonely and Jen quickly wants Dawson back, amidst her Gramps awakening from his coma, only to pass away, leaving the already heartbroken Jen devastated.

Dawson Leery (ex-boyfriend)Pacey Witter (fling)Ty Hicks (ex-boyfriend)C. Braxton (ex-boyfriend)Chris Wolfe (sexual liaison)Charlie Todd (ex-boyfriend)Henry Parker (ex-boyfriend)Drue Valentine (fling)Billy Konrad (ex-boyfriend)Cliff Elliot (ex-boyfriend)Vincent (fling) Jen grew up with her parents in New York and her parents sent her to live with her conservative Christian grandmother (whom she calls "Grams"), and they often clash.

As the series progresses, Grams loosens up and becomes more tolerant and loving.

After the death of Mitch Leery, Dawson invites Jen to the Hookset Film Festival in New Hampshire after he learns that his father entered him in the competition, using his film about now-deceased-director A. After sleeping together, Dawson and Jen begin a relationship, but she breaks it off after realizing that it doesn't feel right.

During the gang's spring break trip to Florida, Jen finds Joey spending time with Charlie and tries to warn Joey about him and speaks with Jack about his drinking problem. when she gets drunk before a gig with Emma's band at Hell's Kitchen. J.'s sexual misadventures only after he tells her that he no longer dates.

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