The paper presents a design exploration into emotional communication through mobile phones for teenagers. A participatory design approach was followed, that lead to the development of two potential enhancements to text messaging services that are feasible with today’s mobile phones. These enhancements refer to using MMS technology for: identifying callers through personalized avatars which are also coupled with context related information for the caller and using semi-automated text enhancements. Preliminary evaluation results are encouraging regarding the value of the emotional and contextual cues that can be conveyed in this way.