Season 2 |
| 23 :02x01 - Sophomoric (Sep/26/1999) | | Felicity returns to college for her sophomore year as a RA, but is still forced to share a room with Meghan. Ben listens to Felicity's tapes to Sally which confirm his worst fears. | |
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| 24 :02x02 - The List (Oct/03/1999) | | Ben breaks up with Felicity, but she is able to get them back together again; however, Felicity realizes that she is compromising herself for Ben and breaks it off again. Felicity decides to chop off all her hair. | |
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| 26 :02x04 - The Depths (Oct/17/1999) | | While stuck on a subway together, Felicity and Julie are forced to deal with their strange relationship. Noel goes on a date with one of Felicity's advisees, Ruby, and Ben hits it off with Maggie, an older woman he meets at work. | | Guest Stars: Amy Smart as Ruby | |
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| 28 :02x06 - The Love Bug (Nov/07/1999) | | Ben realizes that his new crush has a husband. David breaks up with Felicity over her feelings about Noel. Ruby learns of Noel and Felicity's history. | | Guest Stars: Amy Smart as Ruby, Henri Lubatti as David Sherman | |
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| 30 :02x08 - Family Affairs (Nov/21/1999) | | When Felicity decides to stay in New York for Thanksgiving, her parents make a surprise visit. Noel and Elena host Thanksgiving dinner at their apartment, where Felicty and Noel cause friction with David. | | Guest Stars: Henri Lubatti as David Sherman | |
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| 31 :02x09 - Portraits (Dec/19/1999) | | Ben writes a final paper for the wrong novel, Sean tries to find an investor for his new condiment, Smoothaise, and Julie meets with an interested music producer. | | Guest Stars: Henri Lubatti as David Sherman, Amy Smart as Ruby, Adam Rodriguez as Erik Kidd | |
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| 32 :02x10 - Great Expectations (1) (Jan/16/2000) | | Felicity finds out that her parents have separated. When Ben learns that the University swimming program has been cancelled, he and Felicity break into the pool and get caught by security. | | Guest Stars: Adam Rodriguez as Erik Kidd, Amy Smart as Ruby | |
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| 33 :02x11 - Help for the Lovelorn (Jan/23/2000) | | Felicity goes to "The Clinic" to nurse her broken heart in this send-off on the classic "Twilight Zone" television series. | |
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| 34 :02x12 - The Slump (2) (Feb/06/2000) | | In the aftermath of the pool break-in, Ben considers dropping out of school and touring Europe, while Felicity learns about the state of her parents' relationship from her father. | | Guest Stars: Amy Smart as Ruby, Donald Faison as Tracy | |
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| 38 :02x16 - Revolutions (Apr/05/2000) | | Felicity becomes the ringleader of a sit-in to make the morning-after pill available to students in the health clinic. | | Guest Stars: Amy Smart as Ruby | |
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