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As part of a project to evaluate the effectiveness of Tutor.com's Live Homework Help service, the authors examined over 100 transcripts of online transactions between teens and the virtual reference librarians in California who connect students to Live Homework Help tutors. Using content analysis, the authors document and discuss the difference in online communication styles between teens and adults. In addition, the transactions are measured against Reference and User Services Association's (RUSA) reference performance guidelines and are found to be severely lacking in the qualities required for effective reference service. Recommendations are made within the context of positive library service to young adults, including recommendations on how to make virtual reference encounters with teens more responsive to their homework needs.