Brandy Clark (Aubrey Plaza) just graduated valedictorian from her High School and preparing to go to college. To celebrate her friends Fiona (Alia Shawkat) and Wendy (Sarah Steele) take her to a kegger where she lays eyes on Rusty Waters (Scott Porter) and she determines that she must have him, but there is one slight problem, she is a virgin. In being that perfect student Brandy did not have time to pursue parties or boys so what does she do? She does what she has always done, make a list of all the different sexual acts that she has heard or can think of. With list in hand she sets out to broaden her experience and soliciting advice from Fiona, Wendy and her sister Amber (Rachel Bilson) .