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Title: The Sixteen Year Old Virgin (22 Mar 2010)
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| Episode cast overview, first billed only: | |||
| Blake Lively | ... | Serena van der Woodsen | |
| Leighton Meester | ... | Blair Waldorf | |
| Penn Badgley | ... | Dan Humphrey | |
| Chace Crawford | ... | Nate Archibald | |
| Taylor Momsen | ... | Jenny Humphrey | |
| Ed Westwick | ... | Chuck Bass | |
| Jessica Szohr | ... | Vanessa Abrams | |
| Kelly Rutherford | ... | Lily van der Woodsen | |
| Matthew Settle | ... | Rufus Humphrey | |
| Kelly AuCoin | ... | Doug Jarrett | |
| Laura Harring | ... | Elizabeth Fisher | |
| Desmond Harrington | ... | Jack Bass | |
| Caroline Lagerfelt | ... | Celia 'CeCe' Rhodes | |
| Kevin Zegers | ... | Damian Daalgard | |
 |
Stacey Linnartz | ... | Reporter #2 |
Despite being grounded, Jenny continues to see Damien who tells Jenny that he wants to have sex with her. Lily thinks to tell the secret that she has supported conceal, but after a call, she changes of mind. Dan and Vanessa explore a new stage of their friendship. Chuck is forced to make an extremely difficult decision about his hotel. Meanwhile, Serena and Nate have a fight that is reminiscent of past events. Written by CW Publicity
