Lily recalls her past when in a flashback to 1983, the naive and sheltered 17-year-old Lily Rhodes got kicked out of her Santa Barbara boarding school. She ran away to Los Angeles where she tried to re-connect with her divorced and dysfunctional parents; her workaholic record producer father, Rick Rhodes, and the superficial Cece. Lily also met and hooked up with her outgoing free-spirited 19-year-old sister Carol. Carol was the so-called "black sheep" of the family who introduced Lily to the life of partying, as well as Owen, a busboy at Carol's place of employment. Eventually, they all got arrested after crashing a party hosted by the cynical and mean music producer Keith van der Woodsen (Lily's future husband) whom attempted to swindle Carol out of a music deal. In present day New York, Blair and Nate decide to attend their senior prom together. But the evening doesn't turn out exactly as planned, when the Mean Girls attempt to rig the votes for prom king and queen. But Chuck comes to Serena's rescue. Meanwhile, Serena becomes furious when she learns that Lily deliberately had her arrested for her defiance, while Rufus ponders his life and future without Lily, who he snubs for what she did to Serena, as does Eric, Jenny, and even Dan as well whom is forced to bail Serena out of jail himself.
In a flashback to the 80s, 17-year-old Lily Rhodes gets kicked out of boarding school and runs away to Los Angeles, reconnecting with her parents, Rick and Cece, and sister, Carol. Back in present day, Blair and Nate attend prom together, but the evening doesn't turn out exactly as planned and Chuck and Serena have a little something to do with that. Serena and Lily don't see eye-to-eye over Serena's recent run-in with the law.
- In a flashback to the 80s, 17-year-old Lily Rhodes (Brittany Snow) gets kicked out of boarding school and runs away to Los Angeles, reconnecting with her parents, Rick (Andrew McCarthy) and Cece (guest star Cynthia Watros, "Lost"), and sister, Carol (Krysten Ritter). Back in present day, Blair (Leighton Meester) and Nate (Chace Crawford) attend prom together, but the evening doesn't turn out exactly as planned and Chuck (Ed Westwick) has a little something to do with that. Serena (Blake Lively) and Lily (Kelly Rutherford) don't see eye-to-eye over Serenas recent run-in with the law. No Doubt performs in the episode as an 80s band called "Snowed Out." (No Doubt will also debut their cover of the Adam & The Ants tune 'Stand & Deliver' during this episode.) Penn Badgley, Taylor Momsen, Jessica Szohr and Matthew Settle also star. Marc Piznarski directed the episode written by Josh Schwartz & Stephanie Savage