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While Jack seemed certain of his interest in art, and later moreso himself overall as he came to terms with his sexual orientation, he later seems unsure of what he wants in his romantic relationships and also less close-knit with the Capeside gang, save for Jen with whom he manages to reconnect in late Season 5 and the final season. The two have a very close relationship, talking more like friends than siblings at times and end up sharing a friend group as well.Whilst Jack is more reclusive emotionally and socially in the beginning Jack and Jen first meet on a blind date and become close friends when Jen is kicked out of Grams' house and Jack offers that she move in with him.She kisses him back and eventually breaks up with Dawson, shortly after starting to date Jack.The two have a relationship for a while, until Jack comes to terms with being gay.Jack meets Tobey in Season 4, who becomes his first boyfriend.
Although Jack rectifies his academic career, as that is something he wishes to do at the end of Season 5, he is portrayed in relationships as someone who doesn't really want to be in a relationship, but he still has one with David (which does not end well for that exact reason).
Jack befriends Jen and she briefly moves into Jack's house with him, after Andie leaves to receive medical attention, and the two end up moving in with Grams.
Jack's relationships with Jen and Grams changes his life.
From Season 3 onwards, he has a home and steady core of support in his life, his friendship with Jen akin to that of Dawson and Joey – soulmates who connect deeply.
Although Jack and his father mend their relationship and start anew, Andie leaves for Italy and sees his family less frequently for the remainder of the series.
Jack and his younger sister, Andie, arrive in Capeside in 1998 beginning their sophmore year at Capeside High School.