Cimicomorpha is one of the most diverse groups in true bugs, and attract a great attention for a variety of reasons, among them, extraordinary insemination methods in the bed bugs and their relatives (Cimicoidea), feeding-habits alternations in the plant bugs (Miridae), parasitism in the bed bugs and their relatives (Cimicidae and Polyctenidae), agricultural pests in the lace bugs and the plant bugs (Tingidae and Miridae), biological control agents in the minute pirate bugs and the plant bugs (e.g., the genus Orius), disease transmission in the Triatominae (Reduviidae), and micro-habitat transition in the assassin bugs and the flower bugs (Reduviidae and Anthocoridae). In this talk, we propose the phylogenetic relationships within the Cimicomorpha especially including some critical taxa in terms of the biological traits such as haemocoelic insemination and parasitism (e.g., the species belonging to Lasiochilidae, Lyctocoridae, Prostemminae and Corydromius). Based on the phylogenetic results, we also present the evolutionary history of the specialized biological traits of the Cimicomorpha using phylogenetic comparative analyses.