Within the context of an evolutionary theoretical framework, the current research attempted to study the reasons that cause difficulties in starting an intimate relationship in the Greek cultural context. In particular, using qualitative research methods (interviews and open-ended questionnaires), Study 1 (N = 205) identified 58 reasons that make it difficult for people to start an intimate relationship. Using an online sample of 1,095 Greek-speaking participants (N = 1,095), Study 2 classified these reasons in 12 factors. More than 80% of the participants indicated that they faced above moderate or severe difficulties in at least one factor, while about 40% faced difficulties in three or more factors. Significant gender and age effects were found across the different factors. Using second order principal components analysis, the 12 factors were classified in three broader domains of difficulties in starting a relationship.