The current study adds to the literature--and addresses several identified limitations--about the relationship between therapist trainees' personality traits and their preference for a particular theoretical orientation(s). Therapist trainees (N = 197) in a Clinical Psy.D program at The Chicago School of Professional Psychology completed a paper and pencil survey assessing their theoretical predilections, as operationalized by the Counselor Theoretical Position Scale (CTPS)--a measure assessing epistemological factors common across psychological theories--and their personality styles, as defined by the Holland Personality Mosaic (HPM), a commonly available assessment of career personality based on the pioneering work of John Holland. The data was analyzed using Pearson's r correlation and three out of five hypotheses were supported. Namely, students in the sample were predominantly Social types as predicted, and high Artistic scores were correlated with the Intuitive and Subjective dimensions of the CTPS, respectively. Discussion offers a possible rationale for this pattern of results, including the lack of support for two hypotheses. Strengths and weaknesses of the research design are offered, as well as implications for future research and professional practice. [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.]