Considerable work during the past two decades has focused on modeling the structure of semantic memory, although the performance of these models in complex and unconstrained semantic tasks remains relatively understudied. We introduce a two‐player cooperative word game, Connector (based on the boardgame Codenames), and investigate whether similarity metrics derived from two large databases of human free association norms, the University of South Florida norms and the Small World of Words norms, and two distributional semantic models based on large language (...) corpora (word2vec and GloVe) predict performance in this game. Participant dyads were presented with 20‐item word boards with word pairs of varying relatedness. The speaker received a word pair from the board (e.g., exam‐algebra) and generated a one‐word semantic clue (e.g., math), which was used by the guesser to identify the word pair on the board across three attempts. Response times to generate the clue, as well as accuracy and latencies for the guessed word pair, were strongly predicted by the cosine similarity between word pairs and clues in random walk‐based associative models, and to a lesser degree by the distributional models, suggesting that conceptual representations activated during free association were better able to capture search and retrieval processes in the game. Further, the speaker adjusted subsequent clues based on the first attempt by the guesser, who in turn benefited from the adjustment in clues, suggesting a cooperative influence in the game that was effectively captured by both associative and distributional models. These results indicate that both associative and distributional models can capture relatively unconstrained search processes in a cooperative game setting, and Connector is particularly suited to examine communication and semantic search processes. (shrink)