The seniors try to find out who is worthy of an early admission to Yale; Chuck pairs up with an unlikely ally in his war with Jack over Bass Industries.
Lily and Rufus move up their wedding, but complications threaten to tear them apart; Chuck discovers a secret Carter has been keeping from Serena; Dan and Vanessa are pulled into one of Georgina's schemes.
Olivia says something she regrets during a talk show appearance and tries to keep Dan from finding out; Nate suspects that his grandfather will stop at nothing to get Trip elected to congress.
Jenny sets her sights on landing the hottest escort for Cotillion. Dan is upset when Olivia (HILARY DUFF) contemplates leaving school. All-girl French band PLASTISCINES performs.
Serena is put in an awkward position when Lily invites Tripp and Maureen to join them for dinner; Blair suspects her mother of keeping a big secret; Jenny gets even with Eric in the most cruel way.