In March of 2020, state governments in the United States began implementing stay-at-home orders in an attempt to curtail the spread of COVID-19. As a result, most people experienced a decrease in face-to-face interactions as they limited their participation in social gatherings, travel, and in-person work. Although these orders aimed to stop the spread of COVID-19, a potential unintended consequence of these guidelines was an increase in loneliness, which has several negative mental and physical health consequences. The goals of the present study were to investigate the extent that one's romantic relationship status and living arrangements affected self-reports of loneliness and to track how self-reports of loneliness changed over the span of 1 month following the first stay-at-home orders in the United States. Participants (N = 311) reported their loneliness at three time points in 2-week intervals. Results showed considerable overlap between living arrangements and romantic relationship status in predicting loneliness; however, it appears that living with another person has a greater protective effect against loneliness compared to relationship status. That is, whereas living with others or being in a romantic relationship both predicted lower loneliness scores, one's living arrangements accounted for variance in loneliness scores beyond what was accounted for by one's relationship status. The researcher also explored whether loneliness increased across three time points throughout data collection. Results showed that loneliness levels remained approximately the same across time. An unhypothesized interaction effect did emerge between time and age. Subsequent probing of this interact effects showed that young adults experienced the greatest level of loneliness but this loneliness decreased over the month, whereas older adults experienced less loneliness but experienced a small increase in loneliness over the during this time. Together, these results suggest that certain groups of people were more likely to experience loneliness during the COVID-19 pandemic.