Psychotherapists often encounter generational differences between themselves and their adolescent clients. Understanding these differences can enhance the communication, interventions, and trust between the therapist and adolescent client. The use of text messages in the lives of adolescents has increased. While there is emerging literature on the significance of texting for an adolescent’s feelings of connection with his/her peers, much less is known about the addition of this form of communication within counseling sessions. This paper uses one case of conjoint therapy with a father and daughter to explore these issues. The role of texting for the adolescent is explored, the role the texting inhabited in the sessions is discussed, and clinical significance of social media on psychotherapy are explored.