Nord and Bert Couldn't Make Head or Tail of It is a text adventure game revolving around puns and wordplays. Idioms and clichés have become real-world objects in the town of Punster, and the player has to sort them out in order to win. There are seven separate scenarios that can be played in any order, as well as the final one that can be accessed only after having completed all seven. These scenarios are:

- The Shopping Bizarre: Products in a grocery store have been replaced by nonsensical homonyms (such as "chocolate moose"), and the player has to revert them to their normal form.

- Playing Jacks: Equipped with an item called "Jack of All Traits", the player has to construct words beginning with "Jack" to solve puzzles.

- Buy the Farm: Clichéd expressions must be used in their literal meaning while exploring a farm.

- Eat Your Words: More literal idioms used in a diner.

- Act the Part: The protagonist is teleported into a 1950's-style sitcom, where he must perform visual gags.

- Manor of Speaking: The protagonist explores a strange house in a more traditional humorous Infocom-style manner.

- Shake a Tower: Letters in expressions have to be re-arranged to create humorous new meanings.

- Meet the Mayor: The final chapter of the game, mixing elements of the others as the protagonist faces the mayor of Punster.