Betsy Jobs (Kirsten Dunst) and Arlene Lorenzo (Michelle Williams (actress)) are two sweet-natured but somewhat ditzy teenage girls living in Washington D.C. in the early 1970s. Betsy comes from a wealthy family in the Georgetown (Washington, D.C.) area, while Arlene lives with her widowed mother in an apartment in the Watergate Hotel. One night, on a quest to mail a letter to enter a contest to win a date with teen idol singer Bobby Sherman, the two girls sneak out of Arlene's home, at the same time as the Watergate break-in. They manage to enter and leave through the parking garage by taping the latch of a door, accidentally causing the break-in to be discovered. They are seen by G. Gordon Liddy (Harry Shearer), who they believe to be committing a jewel robbery; they panic and run away. The security guard, startled by the taped door, calls the police, who immediately arrest the burglars.