Frank Allen, a professional speaker who lectures on time management has a perfectly ordered and scheduled life, down to the minute. When his wife sets his clock forward 10 minutes as a joke, his day is thrown off. Deciding that his strictly ordered life has done him little good, he begins to make multiple choice index cards, choosing one at random and doing what is written on the card.
Brandy Klark (Aubrey Plaza) is the brainy teen who's always home studying while her friends are out partying. Now, as graduation looms, she starts to realize just how much fun she's been missing out on. Of course Brandy's grades are impressive, but how is a girl who's barely even kissed a guy supposed to handle the freedom of college life? In order to get a leg up, Brandy compiles a list of all of the erotic extracurricular activities she's missed out on and attempts to cross them off one by one. When the task proves more demanding than the previously chaste teen had anticipated, she rounds up a crew of her closest friends to help undertake some hilariously unconventional college prep.
The film is the story of Singe and Kate, a couple from North Somerset, whose lives were turned upside down when Kate was diagnosed with an incurable breast cancer. Over her last few days, she created her list: writing her thoughts and memories down, to help the man she loved create the best life possible for their two sons, after she was gone.