This study examined the relationship between Situational Leadership Theory and empathy as practiced by elementary school teachers in western Kentucky. Teachers from five public school districts in west Kentucky were surveyed to determine their affinity to Situational Leadership Theory and empathy with the added component of helping father-absent boys. Kentucky has a high rate of father-absence as compared to the rest of the United States. However, neither the state-level department of education nor local school districts maintain records of the number of father-absent children. Therefore, research regarding the number of father-absent boys could only be gained through opinion-based questions completed by the teachers who formed the participant group. A series of three research questions examined the relationships between Situational Leadership and empathy, the relationship between teacher gender and empathy, and the relationship between the grade level taught by the teacher and empathy. Two supplemental questions also examined the relationship between teacher empathy and their opinion of the number of father-absent boys in their midst. A survey was distributed to teachers in five public school districts in western Kentucky. The survey contained self-assessments that measured Situational Leadership Theory (LBDQ- XII) and empathy (IRI). Two-Way ANOVA tests were conducted on data produced from a survey distributed to teachers. None of the ANOVA tests produced statistically significant results. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]