As other posters have said, it's a genuinely hard problem that touches on natural language quantification. You can find an excellent resource on the relationshi

As other posters have said, it's a genuinely hard problem that touches on natural language quantification. You can find an excellent resource on the relationship between english words here http://wordnet.princeton.edu/ http://wordnet.princeton.edu/. You could manually rank a set of adjectives and then use wordnet to find synonyms and generate some heuristic from there, but the bottom line is I think it's going to be a huge time sink unless you get someone with NLP experience involved.