Objective: To understand how self-reported malicious intent relates to characteristics of stalking-like behavior among adolescents, including type of stalking-like behavior and number of people targeted. Methods: Data were collected nationally online between 2010 and 2012 from 1,058 adolescents, 14 to 21 years old. Measures included lifetime rates of 6 stalking-like behaviors, self-reported malicious intent (i.e., the explicit intent to frighten, upset, anger, or annoy someone), and 3 psychosocial correlates. Results: Thirty-six percent of youth reported ever engaging in at least 1 of the 6 stalking-like behaviors. “Trying to get someone’s attention by doing something ‘over the top’” and “trying to talk to someone who does not want to talk to you,” representing hyper-intimacy and intrusive pursuit respectively, were the most frequently reported stalking-like behaviors. Eight percent reported engaging in at least 1 of the 6 stalking-like behaviors with malicious intent. Twelve percent reported targeting at least 2 different people. Engaging in these behaviors in-person was most common; online was least common. The odds of reporting stalking-like behavior decreased incrementally with age. Propensity to respond to stimuli with anger and alcohol use were positively associated whereas empathy was negatively associated with the report of perpetrating stalking-like behaviors. Conclusions: Engaging in stalking-like behavior was not uncommon in adolescence, but self-reports of malicious intent were relatively rare. The most frequently reported behaviors may reflect inexperience in youths’ relationship formation and dissolution skills. Health professionals should be aware that adolescents are not immune to engaging in stalking-like behaviors and are willing to answer direct questions about these behaviors and their intent.