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On her day of graduation, Felicity asks a longtime high school crush, Ben, to sign her yearbook; after she reads his message, in which he says that he would have liked to have known her better, Felicity changes her lifelong college plans to follow Ben to a New York school. There, she meets her quirky (and smitten) resident advisor Noel and her first new friend Julie.
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When Felicity learns a male called the admissions office requesting a copy of her application essay, she assumes it was Ben — the subject of said essay — and sends him a copy. Meanwhile, Felicity's parents pop up in New York again.
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Felicity's excited about attending her first college party, and plans to invite Ben — so long as Julie doesn't mind. Meanwhile, Felicity butts heads with a professor, and meets a fellow competitive student Elena.
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After Noel acts on his feelings for Felicity and kisses her during a game of Boggle, the two decide to go on a "maybe date" to discuss the future of their relationship. Julie befriends an aspiring filmmaker.
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After Felicity and Ben are held up, he seems especially spooked and calls on her for late-night chats, one of which includes an invitation to a Halloween party.
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Ben is accused of cheating after Felicity rewrites his paper without telling him; and Julie fears she won't understand a Russian film that Zack is taking her to see.
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Noel tires of hearing about Felicity's goings-on with Ben and forbids her to talk about it with him. Julie and Zack's relationship intensifies. Elena reveals she may be leaving school. Julie's date pushes her too far. Felicity tries to mend fences with Ben. Felicity urges Julie to report the date rape and get counseling, but Julie thinks she caused the incident. Meanwhile, a prospective student visits.
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Noel tires of hearing about Felicity's goings-on with Ben and forbids her to talk about it with him. Julie and Zack's relationship intensifies. Elena reveals she may be leaving school. Julie's date pushes her too far. Felicity tries to mend fences with Ben. Felicity urges Julie to report the date rape and get counseling, but Julie thinks she caused the incident. Meanwhile, a prospective student visits.
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Felicity's hurt when Noel downplays their friendship to his girlfriend, Hanna, who's visiting for Thanksgiving but may transfer to New York. Meanwhile, Elena begrudgingly visits her dad; and Ben can't locate his plane ticket.
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Though finals and Christmas break are fast approaching, Felicity spends most of her study time literally wrapped up in Noel; and helping Ben prepare for a poetry test. Meanwhile, Sean tries to sell fruit to students in the library.