This study examined the relationship between adolescents' attachment style and their decision to enter mentoring relationships. The participants were 569 Greek Cypriot high school students. It was found that adolescents who have a mentor are more secure in their attachment than those who do not. Girls with low scores in secure attachment do not enter easily into mentoring relationships. Older adolescents are more anxious in their attachments, probably because they can better appreciate the possible difficulties if something goes wrong; thus, they are more reluctant to take the risk of starting a mentoring relationship than younger students. Furthermore, secure attachment was found to be positively correlated to the perceived impact of the whole experience: the more secure the attachment, the stronger the mentoring bond seems to be. (Contains 6 tables.)