This study uses data from the past three Population and Housing Censuses to examine trends in singlehood and solitary living among individuals aged 50 and above in Taiwan. The key findings include the following: (1) The never-married rate at age 50 increased from 4.8% to 12.9%, with a larger increase among women. Higher education lowers this rate for men but increases it for women. (2) Single older women show positive educational selection; for men, the pattern is nonlinear. (3) The likelihood of living solitarily among singles aged 50+ declined from 0.61 to 0.44, with men more likely to live solitarily but with a narrowing gender gap. (4) Education positively affects singlehood and solitary living, particularly for women. (5) Continued employment and good health increase solitary living, whereas homeownership reduces it.