This presentation will examine the effectiveness of grouping materials together for comparison or contrast when teaching with primary sources. I will briefly introduce the audience to the types of instruction we do at the Newberry, and then demonstrate an instruction session using images from Newberry materials related to the Gilded Age in Chicago. We will consider each source individually, and then pair them together to evoke a discussion about the depth of information two or three items can lend to each other. We will also review what story or point of view might be missing from these sources, as well as the effectiveness of the demonstration and how it can be adapted for other topics, collections, or institutions.