This iconic episode centers on Dan and Serena's first official date and Jenny's high-stakes entry into Blair's inner circle. :
: Jenny Humphrey is invited to Blair Waldorf’s infamous sleepover. To prove herself, she gets caught in a dangerous game of truth or dare that involves "borrowing" a jacket from a high-end store and breaking her curfew. Gossip_girl_1x05
: Dan Humphrey goes to extreme lengths to impress Serena on their first official date, which ultimately leads to their first kiss. This iconic episode centers on Dan and Serena's