Individuals in pursuit of, or currently in, a romantic relationship typically communicate via technology, extending to sexting with one another. Sexting is commonly understood as the sending and receiving of sexually suggestive or sexually explicit photos, video, or text via cell phone or other technologies. The characteristics that fuel whether one engages in sexting are not well understood. In this study, 459 unmarried, heterosexual undergraduate students (female = 328; male = 131), aged 18 to 25 years, from three universities completed an online questionnaire about their behaviors with technology and romantic relationships. In general, low attachment avoidance and high fear of negative evaluation from the dating partner predicted sending a sexually suggestive photo or video, sending a photo or video in one's underwear or lingerie, and sending a sexually suggestive text. High fear of negative evaluation predicted sending a nude photo or video as well as sending a text message propositioning sex. Low attachment avoidance, greater fear of negative evaluation, and greater social distress when dating were associated with sexting behaviors.