Since the 1960s the higher educational system in the United States has steadily lost its single-sex colleges; and as of 2008 only 51 women's and four men's institutions remain (National Center for Educational Statistics, 2008). Many of the previous single-sex schools have admitted members of the opposite sex, giving in to the national trend of coeducation. Given that single-sex education has become an anomaly, what factors compel these remaining institutions to hold on to their founding missions and continue to educate men or women exclusively? What factors influence students to matriculate at these colleges and what factors influence them to remain enrolled? This dissertation explores these questions at two single-sex colleges: Hampden-Sydney and Sweet Briar. First, a discussion regarding these schools' decisions to remain single-sex is examined. Second, using a qualitative design and George Kuh's theoretical framework of student engagement in a single-sex setting, 32 students, 23 faculty members, and eight administrators were interviewed to gain a better understanding of these two single-sex schools. Documents also were gathered which included admissions figures, graduation rates, first-year retention rates, choice of major, and data from the National Survey of Student Engagement. Analysis of these sources provided a rich description of each college and the students' educational experience both academically and co-curricularly. Conclusions from this research indicate that students share a common collegiate experience regardless of whether they attended Hampden-Sydney or Sweet Briar. Only one of the students interviewed sought to enroll in a single-sex college. The rest of the students decided to matriculate because of the schools' academic programs, extracurricular activities, Honor Code, and the low faculty/student ratio. Secondly, students decided to remain enrolled at either Hampden-Sydney or Sweet Briar because of the single-sex culture, the bonds they formed with faculty, and that they were challenged academically. The students perceive their growth and development to be more significant than their peers who attend larger coeducational institutions. These sentiments are shared by the faculty and administrators who are amazed at the transformation of their students from boys and girls to men and women. All of the students would matriculate again and all but one were adamant that their institution remain single-sex. However, despite the positives outcomes from the research, the higher education market suggests that students prefer a coeducational environment. [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/en-US/products/dissertations/individuals.shtml.]