- Aug/Sept 2005-June 2006: S dated the swimming team captain.
- Tue 10/8/2005: D first met S at a birthday party. This is the setting for his short story "10-08-05" that was published at The New Yorker.
- Aug-Sept 2006: Start of sophomore school year.
- Aug/Sept 2006-June 2006: B develops her eating disorder.
- Between Aug-Dec 2006: The Shepherd's Wedding.
- Thu 11/23/2006: Thanksgiving Day (Flashed back).
- Nov/Dec 2007-Feb 2008: Harold leaves Eleanor for Roman.
- Dec 2007-Jan 2008: S leaves for Connecticut.
- Aug-Sept 2007: Start of school year.
- Thu 10/11/2007: S arrives back from Connecticut, D+J arrive back from Hudson.
- Fri 10/12/2007: S's first day at school, B learns about N+S.
- Sat 10/13/2007: B's Kiss on the Lips party, Lincoln Hawk concert.
- Sun 10/14/2007: Bart Bass' annual brunch.
- Thu 10/18/2007: C catches S going to the center.
- Fri 10/19/2007: Ivy Week-end.
- Sat 10/20/2007: S+B reconcile.
- Sat 10/27/2007: C's "Lost Weekend", B+S's first day together.
- Sun 10/28/2007: B+S's fashion "shoot", C bails out N from Carter Baizen.
- Fri 11/02/2007: B's sleepover, S's first date with D.
- Sat 11/10/2007: Masquerade ball, Eleanor's party for her fashion line.
- Thu 11/15/2007: C informs B on his plans on Victrola.
- Fri 11/16/2007: D+S making out when V arrives via the fire exit.
- Sat 11/17/2007: B does burlesque routine at Victrola, lil J goes to Hudson.
- Sun 11/18/2007: B confesses her sins, J brings Alison home, B's birthday party.
- Mon 11/19/2007: B's birthday.
- Thu 11/22/2007: Thanksgiving Day, the Captain rushed to the Hospital, S, E, D, J learn Lily's past.
The Wild Brunch:
The Handmaiden's Tale:
Blair Waldorf Must Pie!:
Post-Thanksgiving: I haven't paid attention to these episodes (except the last two, although I've seen them all), so I'd have to watch these episodes again to have a good construction of a timeline.
Key: S = Serena, B = Blair, D = Dan, N = Nate, J = Jenny, C = Chuck, V = Vanessa, E = Eric