What is difficult is not usually pleasurable. Yet, for certain unfamiliar figurative language, like that which is common in poetry, while comprehension is often more difficult than for more conventional language, it is in many cases more pleasurable. Concentrating our investigation on verb-based metaphors, we examined whether and to what degree the novel variations (in the form of verb changes and extensions) of conventional verb metaphors were both more difficult to comprehend and yet induced more pleasure. To test this relationship, we developed a set of 62 familiar metaphor stimuli, each with corresponding optimal and excessive verb variation and metaphor extension conditions, and normed these stimuli using both objective measures and participant subjective ratings. We then tested the pleasure-difficulty relationship with an online behavioral study. Based on Rachel Giora and her colleagues' 'optimal innovation hypothesis', we anticipated an inverse U-shaped relationship between ease and pleasure, with an optimal degree of difficulty, introduced by metaphor variations, producing the highest degree of pleasure when compared to familiar or excessive conditions. Results, however, revealed a more complex picture, with only metaphor extension conditions (not verb variation conditions) producing the anticipated pleasure effects. Individual differences in semantic cognition and verbal reasoning assessed using the Semantic Similarities Test, while clearly influential, further complicated the pleasure-difficulty relationship, suggesting an important avenue for further investigation.