Homesickness is a complex phenomenon that operates on a spectrum and impacts individuals' psychological, cognitive, and physical functioning. Sufferers experience a preoccupation of home and a strong desire to return home. In higher education, homesickness among first-year students has been linked to a higher risk of dropping out of school, symptoms of depression and anxiety, and a lack of satisfaction with the overall college experience. Through the lens of belongingness theory, this phenomenological study examined the essence of the homesick experience among first-time undergraduate college students living in the residence halls of a private Catholic college in the Northeast. The seven participants self-identified as experiencing homesickness during their first week away from home and agreed to participate in three semi-structured interviews across the span of the Fall 2020 semester when COVID-19 precautions were in place. Most participants spoke about homesickness as a paradoxical experience filled with mixed emotions. Common triggers of homesickness included reminders of home, a lack of activities and connections, and being alone. Participants indicated that establishing a sense of comfort in their new environment played a central role in reducing symptoms of homesickness. Lastly, the COVID-19 pandemic prolonged students' homesickness and created an additional obstacle from achieving a sense of belonging at college. This study adds important dimensions to the complex nature of homesickness and its progression for first-year college students. Recommendations for parental guardians, higher education administration, and students are outlined for reducing or avoiding homesickness. [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.]