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- Season 2 overviewSep 11, 2003-May 7, 200422 episodesSeason 2 episodes1. I Love You ... Soon Sep 11, 2003
- Holly accidentally tells Henry that she loves him; Val finds herself attracted to her new boss.
- 2. Boys' Club Sep 18, 2003
- Holly is too busy to comfort Henry when he has his teeth pulled.
- 3. When Holly Met Tina Sep 25, 2003
- Holly reluctantly befriends a client's teenage daughter; Val competes with her former boss.
- 4. The Loft Oct 2, 2003
- The girls need to find new office space and a new apartment due to financial strain.
- 5. Like a Virgin (Kinda) Oct 9, 2003
- Holly is shocked to learn that Henry has already lost his virginity.
- 6. No More Mr. Nice Guy Oct 16, 2003
- Val accuses Holly of neglecting Henry in favor of spending time with Vince.
- 7. I'm Sorry, So Sorry Oct 23, 2003
- Holly's plans are dashed by a friend's breakup.
- 8. Partially Obstructed View Oct 30, 2003
- Henry finds out Holly has scored front-row seats to see his favorite band.
- 9. Absence Makes the Heart Grow ... Never Mind Nov 6, 2003
- Val's trip takes an unexpected turn when she finds Peter in the adjoining room.
- 10. The Odd Couple Nov 13, 2003
- Holly feels pulled in different directions when Henry temporarily moves into Vince's apartment.
- 11. Regarding Henry Nov 20, 2003
- Holly searches the city for Henry after they break up; Vince finds out Holly's secret feelings.
- 12. The Incredible Shrinking Group Jan 9, 2004
- Holly asks Gary to set up a meeting with Henry; Val and Lauren try to give up sugar.
- 13. The Hospital Jan 16, 2004
- Holly and Vince share their first kiss; Val and Lauren vie for the attention of a doctor.
- 14. Your Cheatin' Heart Jan 23, 2004
- Holly rushes to tell Vince she spotted Henry with another girl.
- 15. Sky Rink Sucks Jan 30, 2004
- Gary's lying ex-girlfriend disrupts Holly and Vince's plans for Gary's birthday party.
- 16. Lunar Eclipse of the Heart Feb 6, 2004
- Holly decides that dating a cute guy will make Vince jealous; Val and Lauren's friendship is tested.
- 17. Val and Holly's Not Boyfriends Feb 13, 2004
- Holly consoles Vince, then misreads his response; Rick has a near-death experience.
- 18. The Interview Feb 20, 2004
- Holly puts Vince ahead of her future and skips her admissions interview to be with him.
- 19. The Big Picture Apr 16, 2004
- Holly questions her choice to end her relationship with Henry.
- 20. Rollin' in It Apr 23, 2004
- When Holly receives $2,000 from her grandmother, she decides to blow it on a hotel suite.
- 21. The Anti-Prom Apr 30, 2004
- Holly decides to throw a stress-free "anti-prom" party.
- 22. The Second Season Finale May 7, 2004
- When Henry and Vince each kiss her, Holly knows the time has come to choose between them.