Before the game begins, the number of human and computer players must be chosen, as well as the difficulty setting. There must always be at least one human player, and the total number of players (human plus computer opponents) can be no more than four. Players use the controllers to buzz in during the game; if more than two players are competing, they may either share the controllers or use the NES Four Score to allow each one to have his/her own.
Anticipation combines gameplay elements from Pictionary and Trivial Pursuit board games. The player is represented by one of four game pieces on a board: a pair of pink high-heeled shoes, a bugle, an ice cream cone, and a teddy bear. The game slowly draws a picture, and the first person to buzz in may try to guess it. A die counts down from six to zero while the picture is being drawn. As soon as a player buzzes in, the die and the drawing both freeze and the player has 25 seconds to spell out the answer. Making two mistakes, or running out of time, locks the player out; the drawing and the die countdown both resume, and the other players can then buzz in.
Four categories are in play per level, each corresponding to one of the four colors on the board (blue, green, pink, yellow). Correctly solving a puzzle credits the player with its color and moves his/her token by the number of spaces shown on the die; the next puzzle is played in the category for the color on which it lands. If no one solves a puzzle, a new one is played in the same color. Once a player has collected all four colors on a level, the token rises to the next higher level. The first player to complete every level wins the game.