Jen

Jen lives in your dorm and has a crush on you but would never admit it. You and her and a couple of friends (one gay, one girl) were playing poker. None of you had much money, so you bet challenges. The current wager was for the loser to spend the weekend in the winner's dorm room and would be required to honestly and completely answer any question the winner asked. If the loser refused to answer, they had an option to do a task, take off one piece of clothing or some other penality. She lost. You won. The weekend begins now.