Season 2, Episode 1: Sophomoric
　　Original Air Date—26 September 1999
　　Felicity starts her second year at college with a possible new relationship, and the aftermath of her decision to cope with. Elsewhere, housing shortages cause unusual living arrangements.
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　　Season 2, Episode 2: The List
　　Original Air Date—3 October 1999
　　Ben worries about Felicity's expectations of him, Sean and Julie throw a party, and Felicity tries unsuccessfully to counsel one of her charges.
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　　Season 2, Episode 3: Ancient History
　　Original Air Date—10 October 1999
　　Felicity's decision about her hair leads to even more life changes, Julie looks for an apartment, and Noel takes an art class.
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　　Season 2, Episode 4: The Depths
　　Original Air Date—17 October 1999
　　A stalled subway train forces Felicity and Julie to confront each other, Noel and Ruby go to an art show, and Ben stands up to a client.
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　　Season 2, Episode 5: Crash
　　Original Air Date—24 October 1999
　　Noel and Elena become obsessed with a video game, Felicity goes out on a blind date set up by her professor, and Ben is confused by Maggie's actions.
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　　Season 2, Episode 6: The Love Bug
　　Original Air Date—7 November 1999
　　Felicity, Ben, and Noel each deal with uncertainties in their individual relationships, and Mono hits campus just in time for mid-terms.
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　　Season 2, Episode 7: Getting Lucky
　　Original Air Date—14 November 1999
　　A stray dog Felicity picks up on the street impinges on everyone's lives, and provides her with plenty of excuses for not taking the next step with David.
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　　Season 2, Episode 8: Family Affairs
　　Original Air Date—21 November 1999
　　Holiday gatherings are difficult for Felicity and Ben. Ben, because he has to work a party given by Maggie's husband, and Felicity feels pressure from an unexpected family visit and from David.
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　　Season 2, Episode 9: Portraits
　　Original Air Date—19 December 1999
　　Felicity and Noel struggle against feelings for each other while worrying how their actions will affect their grade, Ruby makes a surprise visit, Julie meets a music producer, and Ben is on short-time to complete a final in American Lit.
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　　Season 2, Episode 10: Great Expectations
　　Original Air Date—16 January 2000
　　Felicity's father accepts a position in town, and his never-ending presence begins to grate, Ben reconsiders his decision about Felicity, and Julie begins to doubt the intentions of Erik.
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　　Season 2, Episode 11: Help for the Lovelorn
　　Original Air Date—23 January 2000
　　This episode, a tribute to The Twilight Zone, follows Felicity as she tries to heal her broken heart and strange doings at The Clinic.
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　　Season 2, Episode 12: The Slump
　　Original Air Date—6 February 2000
　　Ben and Felicity are forced into counseling for their prank at the pool, Elena gets a new lab partner, and Noel's argument with Ruby is more serious than he thought.
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　　Season 2, Episode 13: Truth or Consequences
　　Original Air Date—13 February 2000
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　　Season 2, Episode 14: True Colors
　　Original Air Date—20 February 2000
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　　Season 2, Episode 15: Things Change
　　Original Air Date—27 February 2000
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　　Season 2, Episode 16: Revolutions
　　Original Air Date—5 April 2000
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　　Season 2, Episode 17: Docuventary II
　　Original Air Date—12 April 2000
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　　Season 2, Episode 18: Party Lines
　　Original Air Date—19 April 2000
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　　Season 2, Episode 19: Running Mates
　　Original Air Date—26 April 2000
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　　Season 2, Episode 20: Ben Was Here
　　Original Air Date—3 May 2000
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　　Season 2, Episode 21: The Aretha Theory
　　Original Air Date—10 May 2000
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　　Season 2, Episode 22: Final Answer
　　Original Air Date—17 May 2000
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　　Season 2, Episode 23: The Biggest Deal There Is
　　Original Air Date—24 May 2000