Purpose: To evaluate how Video Display Terminal (VDT) use, Contact Lens (CL) wear, and eyedrop use affect ocular surface parameters in participants with ocular discomfort and how these factors may vary across different age groups. Methods: The current cross-sectional study initially involved a total of 252 participants who completed a self-administered survey to collect information about ocular discomfort and lifestyle factors. This online survey was composed of an Ocular Surface Disease Index (OSDI) questionnaire and three extra questions regarding lifestyle factors (VDT use, CL wear, and eyedrop use). Only 185 symptomatic participants, those with OSDI values > 12, were scheduled to undergo a comprehensive ocular examination that included tear film osmolarity, Fluorescein Break-Up Time (FBUT), Maximum Blink Interval (MBI), and corneal staining. Results: Differences in ocular parameters and lifestyle factors across age groups (<40 years, 40–60 years, >60 years) were analyzed, along with their correlations and regression. Significant age group differences were found in OSDI, osmolarity, FBUT, and MBI (One-way ANOVA, all p ≤ 0.029). Correlations were observed between CL wear and osmolarity and MBI (Pearson’s correlation, both p ≤ 0.049). Multiple regression confirmed age associations with OSDI, osmolarity, FBUT, and MBI (Multiple linear regression, all p ≤ 0.040) and found links between VDT use and osmolarity and MBI (Multiple linear regression, both p ≤ 0.038) and between eyedrop use and OSDI (Multiple linear regression, p = 0.040). Conclusion: Aging is a primary factor affecting ocular homeostasis, with older adults showing lower FBUT and MBI values and higher osmolarity. Prolonged use of VDTs exacerbates this effect, further contributing to ocular discomfort and destabilized tear film. No associations between CL wear and any of the ocular parameters were found. Eyedrop use shows varied effects on ocular comfort across age groups, emphasizing the need for age-specific ocular care. Overall, these findings confirm that aging and extended VDT use play a significant role in ocular surface discomfort.