Emoticons have become a common phenomenon in email correspondence between students and professors. Even though the use of emoticons in formal writing is considered inappropriate and unprofessional, more and more students are using these nonverbal communication tools to add context or emphasis to their email messages to professors. This paper examines the association between the use of emoticons and professors' perceptions of higher education students' email messages with and without emoticons in two countries, Serbia and Slovenia. The students' emails were collected and assessed on several levels. The students' messages were examined with particular attention to the appropriateness of the students' writing style. In addition, the students' level of digital literacy, their attitude toward a professor, and gender differences in the use of emoticons were examined. Furthermore, an online questionnaire was used to identify characteristic differences between students who use emoticons and students who do not. The results show that messages with emoticons are rated lower on several dimensions than messages without emoticons. In addition, students who use emoticons show lower digital literacy and perceive their professors as more understanding and helpful. Emoticon use is not related to gender. The results suggest that students should avoid using emoticons even if they have a positive attitude toward their professor.