This study investigates the use of similarities in the form of analogy, metaphor, and simile by students and reviewers in an undergraduate architectural design review. In contrast to studies conducted in vitro settings, this study emphasizes the importance of studying analogies, metaphors, and similes in a natural setting. All similarity relationships were coded according to their type, the level of expertise, range, frequency, goal, value judgment, and depth. The results indicate that analogies, metaphors, and similes were used spontaneously and without any difficulty by both reviewers and students. Reviewers, however, were almost twice as likely to evoke similarities. Metaphor was the most frequently used similarity relationship among the three. It was found that there was a significant relationship between the level of expertise and type of similarity, with students more likely to use analogies and less likely to use similes. It was also found that goal is the most important factor, with a significant relation to all other variables, and that embodiment is often invoked in both students’ and reviewers’ metaphors. We conclude that design education should take full advantage of students’ natural ability to benefit from similarity relationships.