Season 2
Artwork
| # | Image | Title | Aired |
|---|---|---|---|
| 1 |  | Sophomoric | Sep 26, 1999 |
| 2 |  | The List | Oct 3, 1999 |
| 3 |  | Ancient History | Oct 10, 1999 |
| 4 |  | The Depths | Oct 17, 1999 |
| 5 |  | Crash | Oct 24, 1999 |
| 6 |  | The Love Bug | Nov 7, 1999 |
| 7 |  | Getting Lucky | Nov 14, 1999 |
| 8 |  | Family Affairs | Nov 21, 1999 |
| 9 |  | Portraits | Dec 19, 1999 |
| 10 |  | Great Expectations (1) | Jan 16, 2000 |
| 11 |  | Help for the Lovelorn | Jan 23, 2000 |
| 12 |  | The Slump (2) | Feb 6, 2000 |
| 13 |  | Truth or Consequences | Feb 13, 2000 |
| 14 |  | True Colors | Feb 20, 2000 |
| 15 |  | Things Change | Feb 27, 2000 |
| 16 |  | Revolutions | Apr 5, 2000 |
| 17 |  | Docuventary II | Apr 12, 2000 |
| 18 |  | Party Lines | Apr 19, 2000 |
| 19 |  | Running Mates | Apr 26, 2000 |
| 20 |  | Ben Was Here | May 3, 2000 |
| 21 |  | The Aretha Theory | May 10, 2000 |
| 22 |  | Final Answer | May 17, 2000 |
| 23 |  | The Biggest Deal There Is | May 24, 2000 |