Being able to predict whether people agree or disagree with an assertion (i.e. an explicit, selfcontained statement) has several applications ranging from predicting how many people will like or dislike a social media post to classifying posts based on whether they are in accordance with a particular point of view. We formalize this as two NLP tasks: predicting judgments of (i) individuals and (ii) groups based on the text of the assertion and previous judgments. We evaluate a wide range of approaches on a crowdsourced data set containing over 100,000 judgments on over 2,000 assertions. We find that predicting individual judgments is a hard task with our best results only slightly exceeding a majority baseline. Judgments of groups, however, can be more reliably predicted using a Siamese neural network, which outperforms all other approaches by a wide margin.