This dissertation investigates how men’s gender roles and their way of expressing emotions impact on the therapeutic encounter. It is often considered that men have greater difficulty than women engaging intimately and emotionally with their therapist and their social environment. Psychological and social factors are studied to inform the therapeutic work from a psychotherapist’s perspective. This dissertation is a modified systematic literature review which investigates the psychologically oriented literature available on this topic. Emotional constriction was found to be a significant negative factor on mental health issues for many men. Difficulties in family and work relationships, anxiety, depression and men’s attitudes towards help seeking can be linked to men’s inability to express themselves emotionally. The suggestion is made for therapists to be attuned to men’s particular way of connecting- and self-object needs for eschewing overt dependency. Clinical implications are highlighted for the practicing psychotherapist. Further research is recommended as being necessary to establish how gender variables and attitudes across both genders and across cultures affect the therapeutic relationship.