S1·E7 The Headmaster's Daughter

Mr. Elliot is making Ashley's love life difficult by scaring off all potential dates, until Chad comes along and she finally gets to go out. But then she finds out her father the headmaster paid Chad (or Bernie, his real name) to take her out. To get back at him, Ashley pretends to be going out with Lazzarini, which drives Mr. Elliot crazy. Also, Christian blew $400 that was supposed to go toward a ski trip on ski clothes for himself. To replace the funds, he and Jackson enter a contest sponsored by Ms. Dupre in which the winner will cater a faculty dinner. Their competition includes Lauren and Winnie.