This study examined teens’ use of socially interactive technologies (SITs), such as online social sites, cell phones/text messaging, and instant messaging (IM), and the role that social anxiety plays on how teens communicate with others (technologically or face-to-face). Participants included 280 high school students from a large western city. On average, 35–40% of teens reported using cell phones/text messaging and online social sites between 1 and 4 h daily, 24% reported using IMs 1–4 h daily and only 8% reported using email between 1 and 4 h daily. Females tended to use cell phones/text messaging and online social sites more so than did males. In assessing social anxiety, analyses revealed a positive relationship between social anxiety (not comfortable talking with others face-to-face) and (1) talking with others online and (2) talking with others via text messaging. In contrast, there was a positive relationship between the lack of social anxiety (feeling “comfortable” talking with others) and making friends online. Assessing gender differences and social anxiety also revealed significant differences. Results revealed females reported more social anxiety (not comfortable talking with others in person) than did males. In addition, females, more than males, reported feeling more comfortable using SITs (text messaging and online social sites only) rather than talking with others face-to-face.