Background: Sexting, the sharing of sexually suggestive photos, may be a gateway behavior to early sexual activity and increase the likelihood of social ostracism. Methods: Youth Risk Behavior Survey (N = 6021) data from 2015 among Pennsylvania 9th-12th grade students were used to examine associations between consensual and nonconsensual sexting and substance use, mental health, neighborhood safety, and demographic variables. Results: Almost one-third (29%) of students reported consensual sexting, while 3% reported nonconsensual sexting. Female students were 49% less likely to report consensual sexting (OR = 0.69, 95% confidence interval [CI]: [0.54, 0.87]); consensual sexting was significantly more likely in students who reported depressive symptoms (OR = 1.39, 95% CI: [1.10, 1.75]), electronic bullying (OR = 1.46, 95% CI: [1.05, 2.04]), suicide attempts (OR = 1.96, 95% CI: [1.22, 3.17]), current tobacco use (OR = 1.99, 95% CI: [1.30, 3.03]), current alcohol use (OR = 4.23, 95% CI: [3.04, 5.89]), ever having sex (OR = 5.21, 95% CI: [3.87, 7.02]), and reported both ever having sex, and current alcohol use (OR = 7.74, 95% CI: [5.37, 11.14]). Conclusions: High school students, particularly men, that report sexting may be more likely to participate in other risk behaviors and experience negative mental health outcomes. Further research should clarify the temporality of links between sexting, cyberbullying, depression, and suicide to inform mental health screening and treatment availability in high schools.