Word problems are an integral part of any secondary mathematics curriculum and one purpose has been to prepare students for the real-world--for everyday events as well as workplace problem-solving. Prior literature suggests that word problems have not met this objective, in part, because the textbook problems do not mirror the kinds of problems commonly found in real life situations. In this dissertation, I investigate a sample of word problems from two contemporary non-traditional textbooks to uncover the aspects that may influence if and how the problems might be used in the classroom. I utilize a qualitative content analysis with a directed approach, using the literature to guide my initial codes and categories, and allowing other categories and subcategories to emerge during the analysis. I also conduct a numerical analysis of the data to reveal aspects which may be a common thread between the two books. These analyses allow me to answer the research question: Given that the two books chosen for this study have different approaches, what aspects of "realistic-ness" exist in the textbooks' word problems that encourage students to use their real-world knowledge of the context of the problems? This study suggests that changes to the manner in which problems are presented can be beneficial to re-negotiating the didactical contract. Textbook word problems should be posed in a variety of ways, breaking from the tradition of the three-component structure. Additionally, secondary mathematics textbooks should use scaffolding throughout the curricula to afford students the opportunities to grapple with problems as they would in the real world. This study recommends a digital database to organize and update problems with a real-world context. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]