Wit is a form of rich interaction that is often grounded in a specific situation (e.g., a comment in response to an event). In this work, we attempt to build computational models that can produce witty descriptions for a given image. Inspired by a cognitive account of humor appreciation, we employ linguistic wordplay, specifically puns, in image descriptions. We develop two approaches which involve retrieving witty descriptions for a given image from a large corpus of sentences, or generating them via an encoder-decoder neural network architecture. We compare our approach against meaningful baseline approaches via human studies and show substantial improvements. We find that when a human is subject to similar constraints as the model regarding word usage and style, people vote the image descriptions generated by our model to be slightly wittier than human-written witty descriptions. Unsurprisingly, humans are almost always wittier than the model when they are free to choose the vocabulary, style, etc.
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