Gingivitis and periodontitis are highly prevalent in Hong Kong, where the provision of oral health services is predominantly private. This cross-sectional study aimed to investigate the association between the oral symptoms of gum bleeding and self-reported behavioral factors, beliefs, and knowledge among Hong Kong Chinese. The research team commissioned the Public Opinion Programme of The University of Hong Kong to conduct a structured, population-based, computer-assisted telephone interview (CATI), which covered questions related to the demography, perception, and knowledge (including traditional Cantonese beliefs) of gum health, dental attendance, oral health behavior, and dental anxiety. A total of 1,265 individuals aged 25–60 years old were successfully contacted, and 704 (55.7%) reported prior gum bleeding experience. A total of 516 individuals (64.9% females, median 55–60 years) completed the CATI satisfactorily, and 321 (62.2%) experienced gum bleeding in the past 12 months. The factors that were significantly associated with reports of gum bleeding in the past 12 months include having periodontitis, sensitive teeth, having tertiary or higher education, flossing/interdental cleaning, not cleaning teeth well enough, lack of sleep, consuming too much ‘heaty’ food, avoiding going to the dentist when gums are bleeding, and waiting for gum bleeding to subside (p < 0.05, r2 =0.198; forward stepwise logistic regression). Within the limitations of this study, approximately half of the Hong Kong working-age adults surveyed reported experiencing gum bleeding, and 62.2% of the participants experienced it within the past 12 months. Members of Hong Kong’s working-age population who reported having higher levels of education appeared more readily aware of their gum problems. Those with bleeding gums, especially those who have discernable periodontitis, poor dental awareness/behaviors, and/or a poor lifestyle should be targeted to receive education and encouragement, which will allow them to take action and improve their own gum health.