Anticipation combines gameplay elements from Pictionary and Trivial Pursuit board games. The player is represented by one of four game pieces: a pair of pink high-heeled shoes, a horn, an ice cream cone, and a teddy bear. As the game slowly draws a picture, the first person to buzz in and guess the correct answer moves forward on the game board. The number of spaces the player moves depends upon the number on a dice, which counts down from 6 as the picture is drawn. Once a player correctly identifies a drawing for each of the four categories on a level, that player rises to the next-higher game board level. The first player to complete every level wins the game.
There are three levels on the Easy and Medium difficulty settings, and four on the Hard and Very Hard settings. From the third level on, the board includes gray "Feature Squares." Landing on one of these causes the player's token to fly around the board until a button is pressed; a puzzle is then played in the color that was hit. The fourth level has the same layout as the third, but with several gaps where spaces have been removed. Landing on a gap causes the player to fall back down to the corresponding position on the third level, but he/she retains credit for any solved fourth-level puzzles and must answer the remaining categories to climb back up.
Four different categories are used on each game board level, tied to the colors of the spaces (blue, green, pink, yellow). A controller with turbo button control (such as the NES Advantage) can be used to land a token repeatedly on the same Feature Square and force a puzzle to be played from a random category. These puzzles, which have a gray background, do not count toward a player's requirement to solve a puzzle in every category.