In today's world, more adolescents are using the Internet as an avenue for social communication and a source of information and to experiment with risky online behaviors. To better understand how early adolescents are using the Internet, a study was undertaken to more clearly identify online use and online risky behaviors and to describe any online relationships with strangers middle-school students may be participating in. This exploratory study adapted the Youth Internet Safety Survey of Finkelhor et al to identify the usage and characteristics of online youth, solicitation of youth, and risky behaviors. Four hundred and four students, with a mean age of 12 years, were recruited from public and parochial schools located in the Northeast. Findings from this study indicate that of a total sample of 404 middle-school students, a small grouping (n = 59; 14.6%) are beginning risky online communication behaviors with strangers. Students who communicated online with strangers were older and had higher rates of posting personal information, risky online behaviors, and stealing. The majority of this group (84%) met offline with the online stranger, and three students reported having been assaulted. Findings suggest that early adolescents are beginning risky online and offline behaviors. Understanding their experiences is important since they highlight how middle-school students are undertaking risks in a new environment that many adults and parents do not fully understand. Clinicians, educators, healthcare providers, and other professionals need to be informed of Internet behaviors in order to assess for risk, to make referrals, to intervene, and to educate.