This paper introduces Latent Relational Analysis (LRA), a method for measuring relational similarity. LRA has potential applications in many areas, including information extraction, word sense disambiguation, machine translation, and information retrieval. Relational similarity is correspondence between relations, in contrast with attributional similarity, which is correspondence between attributes. When two words have a high degree of attributional similarity, we call them synonyms. When two pairs of words have a high degree of relational similarity, we say that their relations are analogous. For example, the word pair mason/stone is analogous to the pair carpenter/wood. Past work on semantic similarity measures has mainly been concerned with attributional similarity. Recently the Vector Space Model (VSM) of information retrieval has been adapted to the task of measuring relational similarity, achieving a score of 47% on a collection of 374 college-level multiple-choice word analogy questions. In the VSM approach, the relation between a pair of words is characterized by a vector of frequencies of predefined patterns in a large corpus. LRA extends the VSM approach in three ways: (1) the patterns are derived automatically from the corpus (they are not predefined), (2) the Singular Value Decomposition (SVD) is used to smooth the frequency data (it is also used this way in Latent Semantic Analysis), and (3) automatically generated synonyms are used to explore reformulations of the word pairs. LRA achieves 56% on the 374 analogy questions, statistically equivalent to the average human score of 57%. On the related problem of classifying noun-modifier relations, LRA achieves similar gains over the VSM, while using a smaller corpus.