OBJECTIVE We examined loose cigarette (loosie) purchasing behavior among young adult (aged 18-26 years) smokers at bars in New York City and factors associated with purchase and use. METHODS Between June and December 2013, we conducted cross-sectional surveys (n = 1916) in randomly selected bars and nightclubs. Using multivariable logistic regression models, we examined associations of loose cigarette purchasing and use with smoking frequency, price, social norms, cessation behaviors, and demographics. RESULTS Forty-five percent (n = 621) of nondaily smokers and 57% (n = 133) of daily smokers had ever purchased a loosie; 15% of nondaily smokers and 4% of daily smokers reported that their last cigarette was a loosie. Nondaily smokers who never smoked daily were more likely than were daily smokers to have last smoked a loosie (odds ratio = 7.27; 95% confidence interval = 2.35, 22.48). Quitting behaviors and perceived approval of smoking were associated with ever purchasing and recently smoking loosies. CONCLUSIONS Loosie purchase and use is common among young adults, especially nondaily smokers. Smoking patterns and attitudes should be considered to reduce loose cigarette purchasing among young adults in New York City.