Methods and systems that facilitate generating and presenting a crossword puzzle. Methods include obtaining, from a content source, a plurality of data items. Using the plurality of data items, a dictionary of clue-word pairs are generated. A crossword layout is generated using a random crossword layout generator. The generated crossword layout is input to a model that outputs a likelihood that the input crossword layout results in a valid crossword. If the likelihood that the crossword layout results in a valid crossword puzzle satisfies a first threshold, a plurality of words in a set of clue-word pairs from among the plurality of clue-word pairs is inserted into the crossword layout. If the plurality of words inserted into the crossword layout results in a valid crossword puzzle, the crossword puzzle is provided to a user on a user device using the set of clue-word pairs.