Transcripts of chat logs of sexually exploitative interactions between offenders and victims that took place via Internet communication platforms were analysed. The aim of the study was to examine victims’ behaviour and responses to approaches by offenders as part of such interactions, as well as ascertain victims’ motivation for their engagement. The data set comprised five cases, amounting to 29 transcripts, and was analysed using qualitative thematic analysis. Additionally, police reports were reviewed for descriptive and case-specific information. All offenders were men aged between 27 and 52 years (M = 33.6, SD = 5.6). The number of victims with whom offenders communicated ranged from one to twelve (M = 4.6, SD = 4.5). Victims were aged between 11 and 15 years (M = 13.00, SD = 1.2), and were both female (n = 17) and male (n = 6). Our findings highlight that while the majority of young people in this sample appeared to engage in such interactions for reasons of curiosity and sexual exploration/experimentation, other cases involved serious offences of sexual abuse. The victims in these cases presented with a number of vulnerability factors. Findings are discussed in light of conceptualising young people’s negative online experiences along a continuum.