Despite a strong potential for healthy sexual relationships, high functioning individuals with an autism spectrum disorder often struggle with the appropriateness of their courtship behaviours. Using Leslie's (1992) theory of mind (ToM) theory of autism, we investigated two mediators of the association between autistic traits and inappropriate courtship in a non-clinical sample: (1) ToM, and (2) a bias to perceive ambiguous social cues as flirting. University students (N = 195) completed an online battery containing the Autism Quotient (AQ), a measure of inappropriate courtship, a popular test of ToM (Eyes Test-Revised), a measure of flirt perception bias, and a question about singles' venues attendance. AQ was indirectly associated with inappropriate courtship through two pathways: (1) a single-mediator model based on ToM; and (2) a two-mediator serial model with ToM leading to a flirtation perception bias, leading to more frequent inappropriate courtship. Adding flirtation perception and singles' venues attendance to the ToM-mediation model increased the percent of variance accounted for from 17% to 25%, while each mediator remained statistically significant. Sex did not significantly moderate the models. To our knowledge, this is the first model accounting for courtship difficulties in persons with autistic traits. Limitations and applications are considered.